CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Alkene - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy","wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"859689c5-645e-454b-ab3d-e880d7b3f473","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Alkene","wgTitle":"Alkene","wgCurRevisionId":1282619601,"wgRevisionId":1282619601,"wgArticleId":2761,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description is different from Wikidata","Use dmy dates from August 2022","Wikipedia articles needing clarification from September 2023","Alkenes"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Alkene","wgRelevantArticleId":2761,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":50000,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q81406","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGELevelingUpEnabledForUser":false}; RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","mediawiki.page.gallery.styles":"ready","ext.math.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.tablesorter.styles":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.tablesorter","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.quicksurveys.init","ext.growthExperiments.SuggestedEditSession"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.math.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cjquery.tablesorter.styles%7Cmediawiki.page.gallery.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.22"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/c/c3/Ethylene-3D-vdW.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="933"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene-3D-vdW.png/960px-Ethylene-3D-vdW.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="622"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="497"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Alkene - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Alkene"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Alkene&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Alkene"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Alkene rootpage-Alkene skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" title="Main menu" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li><li id="n-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages"><span>Special pages</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Alkene" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Alkene" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Alkene" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Alkene" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Structural_isomerism" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structural_isomerism"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Structural isomerism</span> </div> </a> <ul id="toc-Structural_isomerism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structure_and_bonding" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Structure and bonding</span> </div> </a> <button aria-controls="toc-Structure_and_bonding-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Structure and bonding subsection</span> </button> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> <li id="toc-Bonding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Bonding</span> </div> </a> <ul id="toc-Bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Shape" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Shape"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Shape</span> </div> </a> <ul id="toc-Shape-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isomerism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isomerism"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Isomerism</span> </div> </a> <ul id="toc-Isomerism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Physical properties</span> </div> </a> <button aria-controls="toc-Physical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Physical properties subsection</span> </button> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> <li id="toc-Boiling_and_melting_points" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Boiling_and_melting_points"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Boiling and melting points</span> </div> </a> <ul id="toc-Boiling_and_melting_points-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Infrared_spectroscopy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Infrared_spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Infrared spectroscopy</span> </div> </a> <ul id="toc-Infrared_spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-NMR_spectroscopy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#NMR_spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>NMR spectroscopy</span> </div> </a> <ul id="toc-NMR_spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Combustion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combustion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Combustion</span> </div> </a> <ul id="toc-Combustion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Addition_to_the_unsaturated_bonds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_to_the_unsaturated_bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Addition to the unsaturated bonds</span> </div> </a> <ul id="toc-Addition_to_the_unsaturated_bonds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cycloaddition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cycloaddition"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Cycloaddition</span> </div> </a> <ul id="toc-Cycloaddition-sublist" class="vector-toc-list"> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Polymerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Polymerization</span> </div> </a> <ul id="toc-Polymerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Allylic_substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Allylic_substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Allylic substitution</span> </div> </a> <ul id="toc-Allylic_substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metathesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metathesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Metathesis</span> </div> </a> <ul id="toc-Metathesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_complexation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_complexation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.6</span> <span>Metal complexation</span> </div> </a> <ul id="toc-Metal_complexation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reaction_overview" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reaction_overview"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.7</span> <span>Reaction overview</span> </div> </a> <ul id="toc-Reaction_overview-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Industrial_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Industrial methods</span> </div> </a> <ul id="toc-Industrial_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Elimination_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Elimination reactions</span> </div> </a> <ul id="toc-Elimination_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_from_carbonyl_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis_from_carbonyl_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Synthesis from carbonyl compounds</span> </div> </a> <ul id="toc-Synthesis_from_carbonyl_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_from_alkenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis_from_alkenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Synthesis from alkenes</span> </div> </a> <ul id="toc-Synthesis_from_alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_alkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>From alkynes</span> </div> </a> <ul id="toc-From_alkynes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Rearrangements_and_related_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rearrangements_and_related_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Rearrangements and related reactions</span> </div> </a> <ul id="toc-Rearrangements_and_related_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Application" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Application"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Application</span> </div> </a> <ul id="toc-Application-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Natural occurrence</span> </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-IUPAC_Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#IUPAC_Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>IUPAC Nomenclature</span> </div> </a> <button aria-controls="toc-IUPAC_Nomenclature-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle IUPAC Nomenclature subsection</span> </button> <ul id="toc-IUPAC_Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Cis–trans_isomerism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cis–trans_isomerism"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span><i>Cis</i>–<i>trans</i> isomerism</span> </div> </a> <ul id="toc-Cis–trans_isomerism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Groups_containing_C=C_double_bonds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Groups_containing_C=C_double_bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Groups containing C=C double bonds</span> </div> </a> <ul id="toc-Groups_containing_C=C_double_bonds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Nomenclature links</span> </div> </a> <ul id="toc-Nomenclature_links-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Alkene</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 83 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-83" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">83 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Alkeen" title="Alkeen – Afrikaans" lang="af" hreflang="af" data-title="Alkeen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D9%8A%D9%86" title="ألكين – Arabic" lang="ar" hreflang="ar" data-title="ألكين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Alquenu" title="Alquenu – Asturian" lang="ast" hreflang="ast" data-title="Alquenu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Alkenl%C9%99r" title="Alkenlər – Azerbaijani" lang="az" hreflang="az" data-title="Alkenlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%95%E0%A6%BF%E0%A6%A8" title="অ্যালকিন – Bangla" lang="bn" hreflang="bn" data-title="অ্যালকিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD%D1%8B" title="Алкены – Belarusian" lang="be" hreflang="be" data-title="Алкены" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%BA%D0%B5%D0%BD%D1%8B" title="Алькены – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Алькены" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Alkeno" title="Alkeno – Central Bikol" lang="bcl" hreflang="bcl" data-title="Alkeno" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD" title="Алкен – Bulgarian" lang="bg" hreflang="bg" data-title="Алкен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Alken" title="Alken – Bosnian" lang="bs" hreflang="bs" data-title="Alken" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Alqu%C3%A8" title="Alquè – Catalan" lang="ca" hreflang="ca" data-title="Alquè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Alkeny" title="Alkeny – Czech" lang="cs" hreflang="cs" data-title="Alkeny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Alcen" title="Alcen – Welsh" lang="cy" hreflang="cy" data-title="Alcen" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alken_(kulbrinte)" title="Alken (kulbrinte) – Danish" lang="da" hreflang="da" data-title="Alken (kulbrinte)" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Alkene" title="Alkene – German" lang="de" hreflang="de" data-title="Alkene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alkeenid" title="Alkeenid – Estonian" lang="et" hreflang="et" data-title="Alkeenid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CE%AD%CE%BD%CE%B9%CE%B1" title="Αλκένια – Greek" lang="el" hreflang="el" data-title="Αλκένια" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alqueno" title="Alqueno – Spanish" lang="es" hreflang="es" data-title="Alqueno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Alkeno" title="Alkeno – Esperanto" lang="eo" hreflang="eo" data-title="Alkeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Alkeno" title="Alkeno – Basque" lang="eu" hreflang="eu" data-title="Alkeno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%D9%86" title="آلکن – Persian" lang="fa" hreflang="fa" data-title="آلکن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Alken" title="Alken – Faroese" lang="fo" hreflang="fo" data-title="Alken" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Alc%C3%A8ne" title="Alcène – French" lang="fr" hreflang="fr" data-title="Alcène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Ailc%C3%A9in" title="Ailcéin – Irish" lang="ga" hreflang="ga" data-title="Ailcéin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alqueno" title="Alqueno – Galician" lang="gl" hreflang="gl" data-title="Alqueno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%EC%BC%84" title="알켄 – Korean" lang="ko" hreflang="ko" data-title="알켄" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%AC%D5%AF%D5%A5%D5%B6%D5%B6%D5%A5%D6%80" title="Ալկեններ – Armenian" lang="hy" hreflang="hy" data-title="Ալկեններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%90%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%80%E0%A4%A8" title="ऐल्कीन – Hindi" lang="hi" hreflang="hi" data-title="ऐल्कीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alkeni" title="Alkeni – Croatian" lang="hr" hreflang="hr" data-title="Alkeni" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Alkeno" title="Alkeno – Ido" lang="io" hreflang="io" data-title="Alkeno" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkena" title="Alkena – Indonesian" lang="id" hreflang="id" data-title="Alkena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Alkenar" title="Alkenar – Icelandic" lang="is" hreflang="is" data-title="Alkenar" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alcheni" title="Alcheni – Italian" lang="it" hreflang="it" data-title="Alcheni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%9F" title="אלקן – Hebrew" lang="he" hreflang="he" data-title="אלקן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%B2%E0%B3%8D%E0%B2%95%E0%B3%80%E0%B2%A8%E0%B3%8D" title="ಆಲ್ಕೀನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಆಲ್ಕೀನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%9A%E1%83%99%E1%83%94%E1%83%9C%E1%83%98" title="ალკენი – Georgian" lang="ka" hreflang="ka" data-title="ალკენი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD%D0%B4%D0%B5%D1%80" title="Алкендер – Kazakh" lang="kk" hreflang="kk" data-title="Алкендер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Alken" title="Alken – Kurdish" lang="ku" hreflang="ku" data-title="Alken" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Alkenum" title="Alkenum – Latin" lang="la" hreflang="la" data-title="Alkenum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Alk%C4%93ni" title="Alkēni – Latvian" lang="lv" hreflang="lv" data-title="Alkēni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkenas" title="Alkenas – Lithuanian" lang="lt" hreflang="lt" data-title="Alkenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Alchen" title="Alchen – Lombard" lang="lmo" hreflang="lmo" data-title="Alchen" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alk%C3%A9nek" title="Alkének – Hungarian" lang="hu" hreflang="hu" data-title="Alkének" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD" title="Алкен – Macedonian" lang="mk" hreflang="mk" data-title="Алкен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%86%E0%B5%BD%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%80%E0%B5%BB" title="ആൽക്കീൻ – Malayalam" lang="ml" hreflang="ml" data-title="ആൽക്കീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alkena" title="Alkena – Malay" lang="ms" hreflang="ms" data-title="Alkena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mdf mw-list-item"><a href="https://mdf.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D1%82%D1%82%D0%BD%D0%B5" title="Алкеттне – Moksha" lang="mdf" hreflang="mdf" data-title="Алкеттне" data-language-autonym="Мокшень" data-language-local-name="Moksha" class="interlanguage-link-target"><span>Мокшень</span></a></li><li class="interlanguage-link interwiki-fj mw-list-item"><a href="https://fj.wikipedia.org/wiki/Alkene" title="Alkene – Fijian" lang="fj" hreflang="fj" data-title="Alkene" data-language-autonym="Na Vosa Vakaviti" data-language-local-name="Fijian" class="interlanguage-link-target"><span>Na Vosa Vakaviti</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alkeen" title="Alkeen – Dutch" lang="nl" hreflang="nl" data-title="Alkeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%B1%E3%83%B3" title="アルケン – Japanese" lang="ja" hreflang="ja" data-title="アルケン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alkener" title="Alkener – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Alkener" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Alken" title="Alken – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Alken" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Alkiinii" title="Alkiinii – Oromo" lang="om" hreflang="om" data-title="Alkiinii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Alkenlar" title="Alkenlar – Uzbek" lang="uz" hreflang="uz" data-title="Alkenlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%85%E0%A8%B2%E0%A8%95%E0%A9%80%E0%A8%A8" title="ਅਲਕੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਅਲਕੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkeny" title="Alkeny – Polish" lang="pl" hreflang="pl" data-title="Alkeny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Alceno" title="Alceno – Portuguese" lang="pt" hreflang="pt" data-title="Alceno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Alchen%C4%83" title="Alchenă – Romanian" lang="ro" hreflang="ro" data-title="Alchenă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD%D1%8B" title="Алкены – Rusyn" lang="rue" hreflang="rue" data-title="Алкены" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD%D1%8B" title="Алкены – Russian" lang="ru" hreflang="ru" data-title="Алкены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Alkenet" title="Alkenet – Albanian" lang="sq" hreflang="sq" data-title="Alkenet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alkene" title="Alkene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Alkene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Alk%C3%A9n" title="Alkén – Slovak" lang="sk" hreflang="sk" data-title="Alkén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alken" title="Alken – Slovenian" lang="sl" hreflang="sl" data-title="Alken" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D9%84%DA%A9%DB%8C%D9%86" title="ئەلکین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەلکین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD_(%D1%98%D0%B5%D0%B4%D0%B8%D1%9A%D0%B5%D1%9A%D0%B5)" title="Алкен (једињење) – Serbian" lang="sr" hreflang="sr" data-title="Алкен (једињење)" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Alken" title="Alken – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Alken" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alk%C3%A9na" title="Alkéna – Sundanese" lang="su" hreflang="su" data-title="Alkéna" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Alkeenit" title="Alkeenit – Finnish" lang="fi" hreflang="fi" data-title="Alkeenit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Alken" title="Alken – Swedish" lang="sv" hreflang="sv" data-title="Alken" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Alkeno" title="Alkeno – Tagalog" lang="tl" hreflang="tl" data-title="Alkeno" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%86%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%80%E0%AE%A9%E0%AF%8D" title="ஆல்க்கீன் – Tamil" lang="ta" hreflang="ta" data-title="ஆல்க்கீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/Alkin" title="Alkin – Kabyle" lang="kab" hreflang="kab" data-title="Alkin" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%A5%E0%B8%84%E0%B8%B5%E0%B8%99" title="แอลคีน – Thai" lang="th" hreflang="th" data-title="แอลคีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alken" title="Alken – Turkish" lang="tr" hreflang="tr" data-title="Alken" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B5%D0%BD%D0%B8" title="Алкени – Ukrainian" lang="uk" hreflang="uk" data-title="Алкени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D9%90%DB%8C%D9%86" title="الکِین – Urdu" lang="ur" hreflang="ur" data-title="الکِین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Alken" title="Alken – Vietnamese" lang="vi" hreflang="vi" data-title="Alken" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E7%83%AF%E7%83%B4" title="烯烴 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="烯烴" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Alkeno" title="Alkeno – Waray" lang="war" hreflang="war" data-title="Alkeno" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%83%AF%E7%83%83" title="烯烃 – Wu" lang="wuu" hreflang="wuu" data-title="烯烃" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%83%AF%E7%83%B4" title="烯烴 – Cantonese" lang="yue" hreflang="yue" data-title="烯烴" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%83%AF%E7%83%83" title="烯烃 – Chinese" lang="zh" hreflang="zh" data-title="烯烃" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q81406#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Alkene" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Alkene" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Alkene"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Alkene&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Alkene&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Alkene"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Alkene&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Alkene&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Alkene" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Alkene" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Alkene&oldid=1282619601" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Alkene&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Alkene&id=1282619601&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAlkene"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAlkene"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Alkene&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Alkene&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Alkenes" hreflang="en"><span>Wikimedia Commons</span></a></li><li class="wb-otherproject-link wb-otherproject-wikibooks mw-list-item"><a href="https://en.wikibooks.org/wiki/Organic_Chemistry/Alkenes" hreflang="en"><span>Wikibooks</span></a></li><li class="wb-otherproject-link wb-otherproject-wikiquote mw-list-item"><a href="https://en.wikiquote.org/wiki/Alkene" hreflang="en"><span>Wikiquote</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q81406" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Hydrocarbon compound containing one or more C=C bonds</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Alkane" title="Alkane">alkane</a> or <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">"Olefin" redirects here. For the material, see <a href="/wiki/Olefin_fiber" title="Olefin fiber">olefin fiber</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ethylene-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene-3D-vdW.png/120px-Ethylene-3D-vdW.png" decoding="async" width="120" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene-3D-vdW.png/250px-Ethylene-3D-vdW.png 1.5x" data-file-width="1100" data-file-height="855" /></a><figcaption>A 3D model of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>, the simplest alkene</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>alkene</b>, or <b>olefin</b>, is a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> containing a <a href="/wiki/Carbon" title="Carbon">carbon</a>–carbon <a href="/wiki/Double_bond" title="Double bond">double bond</a>.<sup id="cite_ref-Wade_1-0" class="reference"><a href="#cite_note-Wade-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The double bond may be internal or at the terminal position. Terminal alkenes are also known as <a href="/wiki/Alpha-olefin" class="mw-redirect" title="Alpha-olefin">α-olefins</a>. </p><p>The <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (IUPAC) <a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">recommends using</a> the name "alkene" only for <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> hydrocarbons with just one double bond; <b>alkadiene</b>, <b>alkatriene</b>, etc., or <b><a href="/wiki/Polyene" title="Polyene">polyene</a></b> for acyclic hydrocarbons with two or more double bonds; <b>cycloalkene</b>, <b>cycloalkadiene</b>, etc. for <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds.<sup id="cite_ref-PAC1995.alkenes_2-0" class="reference"><a href="#cite_note-PAC1995.alkenes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PAC1995.olefins_3-0" class="reference"><a href="#cite_note-PAC1995.olefins-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PAC1995_4-0" class="reference"><a href="#cite_note-PAC1995-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Acyclic alkenes, with only one double bond and no other <a href="/wiki/Functional_group" title="Functional group">functional groups</a> (also known as <b>mono-enes</b>) form a <a href="/wiki/Homologous_series" title="Homologous series">homologous series</a> of <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> with the general formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i></sub></span> with <i>n</i> being a >1 natural number (which is two <a href="/wiki/Hydrogen" title="Hydrogen">hydrogens</a> less than the corresponding <a href="/wiki/Alkane" title="Alkane">alkane</a>). When <i>n</i> is four or more, <a href="/wiki/Isomer" title="Isomer">isomers</a> are possible, distinguished by the position and <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">conformation</a> of the double bond. </p><p>Alkenes are generally colorless <a href="/wiki/Polarity_(chemistry)" class="mw-redirect" title="Polarity (chemistry)">non-polar</a> compounds, somewhat similar to alkanes but more reactive. The first few members of the series are gases or liquids at room temperature. The simplest alkene, <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub></span>) (or "ethene" in the <a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC nomenclature</a>) is the <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> produced on the largest scale industrially.<sup id="cite_ref-cenews_5-0" class="reference"><a href="#cite_note-cenews-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">Aromatic</a> compounds are often drawn as cyclic alkenes, however their structure and properties are sufficiently distinct that they are not classified as alkenes or olefins.<sup id="cite_ref-PAC1995.olefins_3-1" class="reference"><a href="#cite_note-PAC1995.olefins-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Hydrocarbons with two overlapping double bonds (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C=C=C</span>) are called <a href="/wiki/Allenes" title="Allenes">allenes</a>—the simplest such compound is itself called <i><a href="/wiki/Propadiene" title="Propadiene">allene</a></i>—and those with three or more overlapping bonds (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C=C=C=C</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C=C=C=C=C</span>, etc.) are called <a href="/wiki/Cumulene" title="Cumulene">cumulenes</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structural_isomerism">Structural isomerism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=1" title="Edit section: Structural isomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes having four or more <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms can form diverse <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a>. Most alkenes are also isomers of <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>. Acyclic alkene structural isomers with only one double bond follow:<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub></span>: <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> only</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">6</sub></span>: <a href="/wiki/Propylene" title="Propylene">propylene</a> only</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">8</sub></span>: 3 isomers: <a href="/wiki/1-Butene" title="1-Butene">1-butene</a>, <a href="/wiki/2-Butene" class="mw-redirect" title="2-Butene">2-butene</a>, and <a href="/wiki/Isobutylene" title="Isobutylene">isobutylene</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">10</sub></span>: 5 isomers: <a href="/wiki/Pentene" title="Pentene">1-pentene</a>, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, <a href="/wiki/2-Methyl-2-butene" title="2-Methyl-2-butene">2-methyl-2-butene</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub></span>: 13 isomers: 1-hexene, 2-hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-methyl-2-pentene, 3-methyl-2-pentene, 4-methyl-2-pentene, 2,3-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, 2-ethyl-1-butene</li></ul> <p>Many of these molecules exhibit <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i>–<i>trans</i> isomerism</a>. There may also be <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> carbon atoms particularly within the larger molecules (from <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub></span>). The number of potential isomers increases rapidly with additional carbon atoms. </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=2" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Bonding">Bonding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=3" title="Edit section: Bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ethylene_3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Ethylene_3D.png/250px-Ethylene_3D.png" decoding="async" width="200" height="223" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Ethylene_3D.png/330px-Ethylene_3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Ethylene_3D.png/500px-Ethylene_3D.png 2x" data-file-width="549" data-file-height="613" /></a><figcaption>Ethylene (ethene), showing the pi bond in green</figcaption></figure> <p>A carbon–carbon double bond consists of a <a href="/wiki/Sigma_bond" title="Sigma bond">sigma bond</a> and a <a href="/wiki/Pi_bond" title="Pi bond">pi bond</a>. This double bond is stronger than a single <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> (611 <a href="/wiki/Joule" title="Joule">kJ</a>/<a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a> for C=C vs. 347 kJ/mol for C–C),<sup id="cite_ref-Wade_1-1" class="reference"><a href="#cite_note-Wade-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> but not twice as strong. Double bonds are shorter than single bonds with an average <a href="/wiki/Bond_length" title="Bond length">bond length</a> of 1.33 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">Å</a> (133 <a href="/wiki/Picometre" title="Picometre">pm</a>) vs 1.53 Å for a typical C-C single bond.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Each carbon atom of the double bond uses its three sp<sup>2</sup> <a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">hybrid orbitals</a> to form sigma bonds to three atoms (the other carbon atom and two hydrogen atoms). The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by the axes of the three sp<sup>2</sup> hybrid orbitals, combine to form the pi bond. This bond lies outside the main C–C axis, with half of the bond on one side of the molecule and a half on the other. With a strength of 65 kcal/mol, the pi bond is significantly weaker than the sigma bond. </p><p>Rotation about the carbon–carbon double bond is restricted because it incurs an energetic cost to break the alignment of the <a href="/wiki/P_orbital" class="mw-redirect" title="P orbital">p orbitals</a> on the two carbon atoms. Consequently <i>cis</i> or <i>trans</i> isomers interconvert so slowly that they can be freely handled at ambient conditions without isomerization. More complex alkenes may be named with the <a href="/wiki/E-Z_notation" class="mw-redirect" title="E-Z notation"><i>E</i>–<i>Z</i> notation</a> for molecules with three or four different <a href="/wiki/Substituent" title="Substituent">substituents</a> (side groups). For example, of the <a href="/wiki/Butene#Isomers" title="Butene">isomers of butene</a>, the two methyl groups of (<i>Z</i>)-but-2<a href="/wiki/-ene" title="-ene">-ene</a> (a.k.a. <i>cis</i>-2-butene) appear on the same side of the double bond, and in (<i>E</i>)-but-2-ene (a.k.a. <i>trans</i>-2-butene) the methyl groups appear on opposite sides. These two isomers of butene have distinct properties. </p> <div class="mw-heading mw-heading3"><h3 id="Shape">Shape</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=4" title="Edit section: Shape"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As predicted by the <a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR</a> model of <a href="/wiki/Electron" title="Electron">electron</a> pair repulsion, the <a href="/wiki/Molecular_geometry" title="Molecular geometry">molecular geometry</a> of alkenes includes <a href="/wiki/Bond_angle" class="mw-redirect" title="Bond angle">bond angles</a> about each carbon atom in a double bond of about 120°. The angle may vary because of <a href="/wiki/Steric_strain" class="mw-redirect" title="Steric strain">steric strain</a> introduced by <a href="/wiki/Nonbonded_interactions" class="mw-redirect" title="Nonbonded interactions">nonbonded interactions</a> between <a href="/wiki/Functional_group" title="Functional group">functional groups</a> attached to the carbon atoms of the double bond. For example, the C–C–C bond angle in <a href="/wiki/Propylene" title="Propylene">propylene</a> is 123.9°. </p><p>For bridged alkenes, <a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a> states that a double bond cannot occur at the bridgehead of a bridged ring system unless the rings are large enough.<sup id="cite_ref-Bansal_8-0" class="reference"><a href="#cite_note-Bansal-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Following Fawcett and defining <i>S</i> as the total number of non-bridgehead atoms in the rings,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> bicyclic systems require <i>S</i> ≥ 7 for stability<sup id="cite_ref-Bansal_8-1" class="reference"><a href="#cite_note-Bansal-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and tricyclic systems require <i>S</i> ≥ 11.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Isomerism">Isomerism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=5" title="Edit section: Isomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">Cis–trans isomerism</a> and <a href="/wiki/E%E2%80%93Z_notation" title="E–Z notation">E–Z notation</a></div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>,the <a href="/wiki/Prefix" title="Prefix">prefixes</a> <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis- and trans-</a> are used to describe the positions of functional groups attached to <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms joined by a double bond. In Latin, <i>cis</i> and <i>trans</i> mean "on this side of" and "on the other side of" respectively. Therefore, if the functional groups are both on the same side of the carbon chain, the bond is said to have <b>cis-</b> configuration, otherwise (i.e. the functional groups are on the opposite side of the carbon chain), the bond is said to have <b>trans-</b> configuration. </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cis-2-Buten.svg" class="mw-file-description" title="structure of cis-2-butene"><img alt="structure of cis-2-butene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Cis-2-Buten.svg/120px-Cis-2-Buten.svg.png" decoding="async" width="120" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Cis-2-Buten.svg/180px-Cis-2-Buten.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Cis-2-Buten.svg/240px-Cis-2-Buten.svg.png 2x" data-file-width="149" data-file-height="91" /></a></span></div> <div class="gallerytext">structure of cis-2-butene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Trans-2-Buten.svg" class="mw-file-description" title="structure of trans-2-butene"><img alt="structure of trans-2-butene" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Trans-2-Buten.svg/120px-Trans-2-Buten.svg.png" decoding="async" width="120" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Trans-2-Buten.svg/180px-Trans-2-Buten.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Trans-2-Buten.svg/240px-Trans-2-Buten.svg.png 2x" data-file-width="149" data-file-height="91" /></a></span></div> <div class="gallerytext">structure of trans-2-butene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Trans-2-butene.svg" class="mw-file-description" title="(E)-But-2-ene"><img alt="(E)-But-2-ene" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Trans-2-butene.svg/120px-Trans-2-butene.svg.png" decoding="async" width="120" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Trans-2-butene.svg/180px-Trans-2-butene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Trans-2-butene.svg/240px-Trans-2-butene.svg.png 2x" data-file-width="512" data-file-height="390" /></a></span></div> <div class="gallerytext">(<i>E</i>)-But-2-ene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cis-2-butene.svg" class="mw-file-description" title="(Z)-But-2-ene"><img alt="(Z)-But-2-ene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cis-2-butene.svg/120px-Cis-2-butene.svg.png" decoding="async" width="120" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cis-2-butene.svg/180px-Cis-2-butene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cis-2-butene.svg/240px-Cis-2-butene.svg.png 2x" data-file-width="512" data-file-height="377" /></a></span></div> <div class="gallerytext">(<i>Z</i>)-But-2-ene</div> </li> </ul> <p>For there to be cis- and trans- configurations, there must be a carbon chain, or at least one <a href="/wiki/Functional_group" title="Functional group">functional group</a> attached to each carbon is the same for both. <a href="/wiki/E%E2%80%93Z_notation" title="E–Z notation">E- and Z- configuration</a> can be used instead in a more general case where all four functional groups attached to carbon atoms in a double bond are different. E- and Z- are abbreviations of German words <i>zusammen</i> (together) and <i>entgegen</i> (opposite). In E- and Z-isomerism, each functional group is assigned a priority based on the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">Cahn–Ingold–Prelog priority rules</a>. If the two groups with higher priority are on the same side of the double bond, the bond is assigned <b>Z-</b> configuration, otherwise (i.e. the two groups with higher priority are on the opposite side of the double bond), the bond is assigned <b>E-</b> configuration. Cis- and trans- configurations do not have a fixed relationship between <b>E</b>- and <b>Z</b>-configurations. </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=6" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many of the physical properties of alkenes and <a href="/wiki/Alkane" title="Alkane">alkanes</a> are similar: they are colorless, nonpolar, and combustible. The <a href="/wiki/Physical_state" class="mw-redirect" title="Physical state">physical state</a> depends on <a href="/wiki/Molecular_mass" title="Molecular mass">molecular mass</a>: like the corresponding saturated hydrocarbons, the simplest alkenes (<a href="/wiki/Ethylene" title="Ethylene">ethylene</a>, <a href="/wiki/Propylene" title="Propylene">propylene</a>, and <a href="/wiki/Butene" title="Butene">butene</a>) are gases at room temperature. Linear alkenes of approximately five to sixteen carbon atoms are liquids, and higher alkenes are waxy solids. The melting point of the solids also increases with increase in molecular mass. </p><p>Alkenes generally have stronger smells than their corresponding alkanes. Ethylene has a sweet and musty odor. Strained alkenes, in particular, like norbornene and <a href="/wiki/Trans-Cyclooctene" title="Trans-Cyclooctene"><i>trans</i>-cyclooctene</a> are known to have strong, unpleasant odors, a fact consistent with the stronger π complexes they form with metal ions including copper.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Boiling_and_melting_points">Boiling and melting points</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=7" title="Edit section: Boiling and melting points"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Below is a list of the boiling and melting points of various alkenes with the corresponding alkane and alkyne analogues.<sup id="cite_ref-alkene_properties_12-0" class="reference"><a href="#cite_note-alkene_properties-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Melting and boiling points in <a href="/wiki/Celsius" title="Celsius">°C</a> </caption> <tbody><tr> <th>Number of<br />carbons </th> <th> </th> <th>Alkane </th> <th>Alkene </th> <th>Alkyne </th></tr> <tr> <td rowspan="3">2 </td> <td>Name</td> <td>ethane</td> <td>ethylene</td> <td>acetylene </td></tr> <tr> <td>Melting point</td> <td>−183</td> <td>−169</td> <td>−80.7 </td></tr> <tr> <td>Boiling point</td> <td>−89</td> <td>−104</td> <td>−84.7 </td></tr> <tr> <td rowspan="3">3 </td> <td>Name</td> <td>propane</td> <td>propylene</td> <td>propyne </td></tr> <tr> <td>Melting point</td> <td>−190</td> <td>−185</td> <td>−102.7 </td></tr> <tr> <td>Boiling point</td> <td>−42</td> <td>−47</td> <td>−23.2 </td></tr> <tr> <td rowspan="3">4 </td> <td>Name</td> <td>butane</td> <td>1-butene</td> <td>1-butyne </td></tr> <tr> <td>Melting point</td> <td>−138</td> <td>−185.3</td> <td>−125.7 </td></tr> <tr> <td>Boiling point</td> <td>−0.5</td> <td>−6.2</td> <td>8.0 </td></tr> <tr> <td rowspan="3">5 </td> <td>Name</td> <td>pentane</td> <td>1-pentene</td> <td>1-pentyne </td></tr> <tr> <td>Melting point</td> <td>−130</td> <td>−165.2</td> <td>−90.0 </td></tr> <tr> <td>Boiling point</td> <td>36</td> <td>29.9</td> <td>40.1 </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Infrared_spectroscopy">Infrared spectroscopy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=8" title="Edit section: Infrared spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Infrared" title="Infrared">IR</a> spectrum, the stretching/compression of C=C bond gives a peak at 1670–1600 <a href="/wiki/Wave_number" class="mw-redirect" title="Wave number">cm<sup>−1</sup></a>. The band is weak in symmetrical alkenes. The bending of C=C bond absorbs between 1000 and 650 cm<sup>−1</sup> wavelength </p> <div class="mw-heading mw-heading3"><h3 id="NMR_spectroscopy">NMR spectroscopy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=9" title="Edit section: NMR spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <sup>1</sup>H <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> spectroscopy, the <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> bonded to the carbon adjacent to double bonds will give a <a href="/wiki/Chemical_shift" title="Chemical shift">δ<sub>H</sub></a> of 4.5–6.5 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a>. The double bond will also <a href="/wiki/Electromagnetic_shielding" title="Electromagnetic shielding">deshield</a> the hydrogen attached to the carbons adjacent to sp<sup>2</sup> carbons, and this generates δ<sub>H</sub>=1.6–2. ppm peaks.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Cis/trans isomers are distinguishable due to different <a href="/wiki/J-coupling" title="J-coupling">J-coupling</a> effect. Cis <a href="/wiki/Vicinal_(chemistry)" title="Vicinal (chemistry)">vicinal</a> hydrogens will have coupling constants in the range of 6–14 <a href="/wiki/Hz" class="mw-redirect" title="Hz">Hz</a>, whereas the trans will have coupling constants of 11–18 Hz.<sup id="cite_ref-NMR_of_Alkenes_15-0" class="reference"><a href="#cite_note-NMR_of_Alkenes-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>In their <sup>13</sup>C NMR spectra of alkenes, double bonds also deshield the carbons, making them have low field shift. C=C double bonds usually have chemical shift of about 100–170 ppm.<sup id="cite_ref-NMR_of_Alkenes_15-1" class="reference"><a href="#cite_note-NMR_of_Alkenes-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Combustion">Combustion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=10" title="Edit section: Combustion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like most other <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a>, alkenes <a href="/wiki/Combustion" title="Combustion">combust</a> to give carbon dioxide and water. </p><p>The combustion of alkenes release less energy than burning same <a href="/wiki/Molarity" class="mw-redirect" title="Molarity">molarity</a> of saturated ones with same number of carbons. This trend can be clearly seen in the list of <a href="/wiki/Enthalpy_of_combustion" class="mw-redirect" title="Enthalpy of combustion">standard enthalpy of combustion</a> of hydrocarbons.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Combustion energies of various hydrocarbons </caption> <tbody><tr> <th>Number of<br />carbons </th> <th>Substance </th> <th>Type </th> <th>Formula </th> <th>H<sub>c</sub><sup>ø</sup><br />(kJ/mol) </th></tr> <tr> <td rowspan="3">2 </td> <td><a href="/wiki/Ethane" title="Ethane">ethane</a> </td> <td>saturated </td> <td>C<sub>2</sub>H<sub>6</sub> </td> <td>−1559.7 </td></tr> <tr> <td><a href="/wiki/Ethylene" title="Ethylene">ethylene</a> </td> <td>unsaturated </td> <td>C<sub>2</sub>H<sub>4</sub> </td> <td>−1410.8 </td></tr> <tr> <td><a href="/wiki/Acetylene" title="Acetylene">acetylene</a> </td> <td>unsaturated </td> <td>C<sub>2</sub>H<sub>2</sub> </td> <td>−1300.8 </td></tr> <tr> <td rowspan="3">3 </td> <td><a href="/wiki/Propane" title="Propane">propane</a> </td> <td>saturated </td> <td>CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> </td> <td>−2219.2 </td></tr> <tr> <td><a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a> </td> <td>unsaturated </td> <td>CH<sub>3</sub>CH=CH<sub>2</sub> </td> <td>−2058.1 </td></tr> <tr> <td><a href="/wiki/Propyne" title="Propyne">propyne</a> </td> <td>unsaturated </td> <td>CH<sub>3</sub>C≡CH </td> <td>−1938.7 </td></tr> <tr> <td rowspan="3">4 </td> <td><a href="/wiki/Butane" title="Butane">butane</a> </td> <td>saturated </td> <td>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> </td> <td>−2876.5 </td></tr> <tr> <td><a href="/wiki/1-butene" class="mw-redirect" title="1-butene">1-butene</a> </td> <td>unsaturated </td> <td>CH<sub>2</sub>=CH−CH<sub>2</sub>CH<sub>3</sub> </td> <td>−2716.8 </td></tr> <tr> <td><a href="/wiki/1-butyne" class="mw-redirect" title="1-butyne">1-butyne</a> </td> <td>unsaturated </td> <td>CH≡C-CH<sub>2</sub>CH<sub>3</sub> </td> <td>−2596.6 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=11" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes are relatively stable compounds, but are more reactive than <a href="/wiki/Alkane" title="Alkane">alkanes</a>. Most reactions of alkenes involve additions to this pi bond, forming new <a href="/wiki/Sigma_bond" title="Sigma bond">single bonds</a>. Alkenes serve as a feedstock for the <a href="/wiki/Petrochemical_industry" title="Petrochemical industry">petrochemical industry</a> because they can participate in a wide variety of reactions, prominently polymerization and alkylation. Except for ethylene, alkenes have two sites of reactivity: the carbon–carbon pi-bond and the presence of <a href="/wiki/Allylic" class="mw-redirect" title="Allylic">allylic</a> CH centers. The former dominates but the allylic sites are important too. </p> <div class="mw-heading mw-heading3"><h3 id="Addition_to_the_unsaturated_bonds">Addition to the unsaturated bonds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=12" title="Edit section: Addition to the unsaturated bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ear.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ear.png/400px-Ear.png" decoding="async" width="400" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ear.png/600px-Ear.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ear.png/800px-Ear.png 2x" data-file-width="1594" data-file-height="300" /></a><figcaption>typical electrophilic addition reaction of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a></figcaption></figure> <p><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> involves the addition of <a href="/wiki/Hydrogen" title="Hydrogen">H<sub>2</sub></a> ,resulting in an alkane. The equation of hydrogenation of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> to form <a href="/wiki/Ethane" title="Ethane">ethane</a> is: </p> <dl><dd>H<sub>2</sub>C=CH<sub>2</sub> + H<sub>2</sub>→H<sub>3</sub>C−CH<sub>3</sub></dd></dl> <p>Hydrogenation reactions usually require <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> to increase their <a href="/wiki/Reaction_rate" title="Reaction rate">reaction rate</a>. The total number of hydrogens that can be added to an unsaturated hydrocarbon depends on its <a href="/wiki/Degree_of_unsaturation" title="Degree of unsaturation">degree of unsaturation</a>. </p><p>Similarly, <a href="/wiki/Halogenation" title="Halogenation">halogenation</a> involves the addition of a halogen molecule, such as <a href="/wiki/Bromine" title="Bromine">Br<sub>2</sub></a>, resulting in a dihaloalkane. The equation of bromination of ethylene to form ethane is: </p> <dl><dd>H<sub>2</sub>C=CH<sub>2</sub> + Br<sub>2</sub>→H<sub>2</sub>CBr−CH<sub>2</sub>Br</dd></dl> <p>Unlike hydrogenation, these halogenation reactions do not require catalysts. The reaction occurs in two steps, with a <a href="/wiki/Halonium_ion" title="Halonium ion">halonium ion</a> as an intermediate. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/250px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" decoding="async" width="170" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/330px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/500px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 2x" data-file-width="1100" data-file-height="712" /></a><figcaption>Structure of a <a href="/wiki/Bromonium_ion" class="mw-redirect" title="Bromonium ion">bromonium ion</a></figcaption></figure> <p><a href="/wiki/Bromine_test" title="Bromine test">Bromine test</a> is used to test the saturation of hydrocarbons.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The bromine test can also be used as an indication of the <a href="/wiki/Degree_of_unsaturation" title="Degree of unsaturation">degree of unsaturation</a> for unsaturated hydrocarbons. <a href="/wiki/Bromine_number" title="Bromine number">Bromine number</a> is defined as gram of bromine able to react with 100g of product.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Similar as hydrogenation, the halogenation of bromine is also depend on the number of π bond. A higher bromine number indicates higher degree of unsaturation. </p><p>The π bonds of alkenes hydrocarbons are also susceptible to <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a>. The reaction usually involves <a href="/wiki/Strong_acid" class="mw-redirect" title="Strong acid">strong acid</a> as <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The first step in hydration often involves formation of a <a href="/wiki/Carbocation" title="Carbocation">carbocation</a>. The net result of the reaction will be an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. The reaction equation for hydration of ethylene is: </p> <dl><dd>H<sub>2</sub>C=CH<sub>2</sub> + H<sub>2</sub>O→<a href="/wiki/Ethanol" title="Ethanol"><span class="tmpl-colored-link" style="color: black; text-decoration: inherit;">H<sub>3</sub>C-CH<sub>2</sub>OH</span></a></dd></dl> <figure typeof="mw:File/Thumb"><a href="/wiki/File:HBr-addition.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/HBr-addition.svg/500px-HBr-addition.svg.png" decoding="async" width="350" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/HBr-addition.svg/960px-HBr-addition.svg.png 1.5x" data-file-width="1384" data-file-height="221" /></a><figcaption>Example of hydrohalogenation: addition of <a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">HBr</a> to an alkene</figcaption></figure> <p><a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a> involves addition of H−X to unsaturated hydrocarbons. This reaction results in new C−H and C−X σ bonds. The formation of the intermediate carbocation is selective and follows <a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov's rule</a>. The hydrohalogenation of alkene will result in <a href="/wiki/Haloalkane" title="Haloalkane">haloalkane</a>. The reaction equation of HBr addition to ethylene is: </p> <dl><dd>H<sub>2</sub>C=CH<sub>2</sub> + HBr → <a href="/wiki/Bromoethane" title="Bromoethane"><span class="tmpl-colored-link" style="color: black; text-decoration: inherit;">H<sub>3</sub>C−CH<sub>2</sub>Br</span></a></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Cycloaddition">Cycloaddition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=13" title="Edit section: Cycloaddition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Diels-Alder_(1,3-butadiene_%2B_ethylene)_red.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg/250px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg.png" decoding="async" width="220" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg/330px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg/500px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29_red.svg.png 2x" data-file-width="638" data-file-height="227" /></a><figcaption>a Diels-Alder reaction</figcaption></figure> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:4%2B2_cycloaddition_cyclopentadiene_O2.svg" class="mw-file-description"><img alt="Generation of singlet oxygen and its [4+2]-cycloaddition with cyclopentadiene" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/4%2B2_cycloaddition_cyclopentadiene_O2.svg/350px-4%2B2_cycloaddition_cyclopentadiene_O2.svg.png" decoding="async" width="350" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/4%2B2_cycloaddition_cyclopentadiene_O2.svg/525px-4%2B2_cycloaddition_cyclopentadiene_O2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/4%2B2_cycloaddition_cyclopentadiene_O2.svg/700px-4%2B2_cycloaddition_cyclopentadiene_O2.svg.png 2x" data-file-width="304" data-file-height="136" /></a><figcaption></figcaption></figure> <p>Alkenes add to <a href="/wiki/Diene" title="Diene">dienes</a> to give <a href="/wiki/Cyclohexene" title="Cyclohexene">cyclohexenes</a>. This conversion is an example of a <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a>. Such reaction proceed with retention of stereochemistry. The rates are sensitive to electron-withdrawing or electron-donating substituents. When irradiated by UV-light, alkenes dimerize to give <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutanes</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Another example is the <a href="/wiki/Ene_reaction#Singlet-oxygen_ene_reaction" title="Ene reaction">Schenck ene reaction</a>, in which singlet oxygen reacts with an <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> structure to give a transposed allyl <a href="/wiki/Peroxide" title="Peroxide">peroxide</a>: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Schenck_ene_reaction.svg" class="mw-file-description"><img alt="Reaction of singlet oxygen with an allyl structure to give allyl peroxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Schenck_ene_reaction.svg/200px-Schenck_ene_reaction.svg.png" decoding="async" width="200" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Schenck_ene_reaction.svg/300px-Schenck_ene_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Schenck_ene_reaction.svg/400px-Schenck_ene_reaction.svg.png 2x" data-file-width="137" data-file-height="46" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Oxidation">Oxidation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=14" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes react with <a href="/wiki/Peroxy_acid" title="Peroxy acid">percarboxylic acids</a> and even hydrogen peroxide to yield <a href="/wiki/Epoxide" title="Epoxide">epoxides</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">RCH=CH<sub class="template-chem2-sub">2</sub> + RCO<sub class="template-chem2-sub">3</sub>H → RCHOCH<sub class="template-chem2-sub">2</sub> + RCO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <p>For ethylene, the <a href="/wiki/Epoxidation" class="mw-redirect" title="Epoxidation">epoxidation</a> is conducted on a very large scale industrially using oxygen in the presence of silver-based catalysts: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub> + 1/<sub class="template-chem2-sub">2</sub> O<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>O</span></dd></dl> <p>Alkenes react with ozone, leading to the scission of the double bond. The process is called <a href="/wiki/Ozonolysis" title="Ozonolysis">ozonolysis</a>. Often the reaction procedure includes a mild reductant, such as dimethylsulfide (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">SMe<sub class="template-chem2-sub">2</sub></span>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">RCH=CHR' + O<sub class="template-chem2-sub">3</sub> + SMe<sub class="template-chem2-sub">2</sub> → RCHO + R'CHO + O=SMe<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C=CHR' + O<sub class="template-chem2-sub">3</sub> → R<sub class="template-chem2-sub">2</sub>CHO + R'CHO + O=SMe<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>When treated with a hot concentrated, acidified solution of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap"><a href="/wiki/Potassium_permanganate" title="Potassium permanganate">KMnO<sub class="template-chem2-sub">4</sub></a></span>, alkenes are cleaved to form <a href="/wiki/Ketone" title="Ketone">ketones</a> and/or <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>. The stoichiometry of the reaction is sensitive to conditions. This reaction and the ozonolysis can be used to determine the position of a double bond in an unknown alkene. </p><p>The oxidation can be stopped at the <a href="/wiki/Vicinal_(chemistry)" title="Vicinal (chemistry)">vicinal</a> <a href="/wiki/Diol" title="Diol">diol</a> rather than full cleavage of the alkene by using <a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">osmium tetroxide</a> or other oxidants: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R'CH=CR2 + 1/2 O2 + H2O -> R'CH(OH)-C(OH)R2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CR</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <mstyle displaystyle="false" scriptlevel="0"> <mfrac> <mn>1</mn> <mn>2</mn> </mfrac> </mstyle> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R'CH=CR2 + 1/2 O2 + H2O -> R'CH(OH)-C(OH)R2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/b9b11bf68bf9f68d3a71c16df1783a2e37eb24d8" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.171ex; width:54.759ex; height:3.509ex;" alt="{\displaystyle {\ce {R'CH=CR2 + 1/2 O2 + H2O -> R'CH(OH)-C(OH)R2}}}" /></span></dd></dl> <p>This reaction is called <a href="/wiki/Dihydroxylation" title="Dihydroxylation">dihydroxylation</a>. </p><p>In the presence of an appropriate <a href="/wiki/Photosensitiser" class="mw-redirect" title="Photosensitiser">photosensitiser</a>, such as <a href="/wiki/Methylene_blue" title="Methylene blue">methylene blue</a> and light, alkenes can undergo reaction with reactive oxygen species generated by the photosensitiser, such as <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radicals</a>, <a href="/wiki/Singlet_oxygen" title="Singlet oxygen">singlet oxygen</a> or <a href="/wiki/Superoxide" title="Superoxide">superoxide</a> ion. Reactions of the excited sensitizer can involve electron or hydrogen transfer, usually with a reducing substrate (Type I reaction) or interaction with oxygen (Type II reaction).<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> These various alternative processes and reactions can be controlled by choice of specific reaction conditions, leading to a wide range of products. A common example is the [4+2]-<a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> of singlet oxygen with a <a href="/wiki/Diene" title="Diene">diene</a> such as <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> to yield an <a href="/wiki/Endoperoxide" class="mw-redirect" title="Endoperoxide">endoperoxide</a>: </p> <div class="mw-heading mw-heading3"><h3 id="Polymerization">Polymerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=15" title="Edit section: Polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Polyolefin" title="Polyolefin">polyolefin</a></div> <p>Terminal alkenes are precursors to <a href="/wiki/Polymer" title="Polymer">polymers</a> via processes termed <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>. Some polymerizations are of great economic significance, as they generate the plastics <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> and <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>. Polymers from alkene are usually referred to as <i><a href="/wiki/Polyolefin" title="Polyolefin">polyolefins</a></i> although they contain no olefins. Polymerization can proceed via diverse mechanisms. <a href="/wiki/Conjugated_system" title="Conjugated system">Conjugated</a> <a href="/wiki/Diene" title="Diene">dienes</a> such as <a href="/wiki/Buta-1,3-diene" class="mw-redirect" title="Buta-1,3-diene">buta-1,3-diene</a> and <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> (2-methylbuta-1,3-diene) also produce polymers, one example being natural rubber. </p> <div class="mw-heading mw-heading3"><h3 id="Allylic_substitution">Allylic substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=16" title="Edit section: Allylic substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The presence of a C=C π bond in unsaturated hydrocarbons weakens the dissociation energy of the <a href="/wiki/Allylic" class="mw-redirect" title="Allylic">allylic</a> C−H bonds. Thus, these groupings are susceptible to <a href="/wiki/Free_radical_substitution" class="mw-redirect" title="Free radical substitution">free radical substitution</a> at these C-H sites as well as addition reactions at the C=C site. In the presence of <a href="/wiki/Radical_initiator" title="Radical initiator">radical initiators</a>, allylic C-H bonds can be halogenated.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The presence of two C=C bonds flanking one methylene, i.e., doubly allylic, results in particularly weak HC-H bonds. The high reactivity of these situations is the basis for certain free radical reactions, manifested in the chemistry of <a href="/wiki/Drying_oil" title="Drying oil">drying oils</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Metathesis">Metathesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=17" title="Edit section: Metathesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes undergo <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>, which cleaves and interchanges the substituents of the alkene. A related reaction is <a href="/wiki/Ethenolysis" title="Ethenolysis">ethenolysis</a>:<sup id="cite_ref-JFH_23-0" class="reference"><a href="#cite_note-JFH-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\overset {\text{diisobutene}}{{\ce {(CH3)3C-CH=C(CH3)2}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{neohexane}}{{\ce {(CH3)3C-CH=}}{\color {red}{\ce {CH2}}}}}+{\ce {(CH3)2C=}}{\color {red}{\ce {CH2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>C</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> <mtext>diisobutene</mtext> </mover> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> </mrow> <mtext>neohexane</mtext> </mover> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\overset {\text{diisobutene}}{{\ce {(CH3)3C-CH=C(CH3)2}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{neohexane}}{{\ce {(CH3)3C-CH=}}{\color {red}{\ce {CH2}}}}}+{\ce {(CH3)2C=}}{\color {red}{\ce {CH2}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/93b6179061564347ca8a0365a44799899a0c55a7" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:82.438ex; height:4.843ex;" alt="{\displaystyle {\overset {\text{diisobutene}}{{\ce {(CH3)3C-CH=C(CH3)2}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{neohexane}}{{\ce {(CH3)3C-CH=}}{\color {red}{\ce {CH2}}}}}+{\ce {(CH3)2C=}}{\color {red}{\ce {CH2}}}}" /></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Metal_complexation">Metal complexation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=18" title="Edit section: Metal complexation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:DCDmodel.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/DCDmodel.png/250px-DCDmodel.png" decoding="async" width="220" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/DCDmodel.png/330px-DCDmodel.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/DCDmodel.png/500px-DCDmodel.png 2x" data-file-width="2210" data-file-height="948" /></a><figcaption>The <a href="/wiki/Dewar-Chatt-Duncanson_model" class="mw-redirect" title="Dewar-Chatt-Duncanson model">Dewar-Chatt-Duncanson model</a> for alkene-metal bonding.</figcaption></figure> <dl><dd><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ni(cod)2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ni%28cod%292.png/250px-Ni%28cod%292.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ni%28cod%292.png/330px-Ni%28cod%292.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ni%28cod%292.png/440px-Ni%28cod%292.png 2x" data-file-width="477" data-file-height="258" /></a><figcaption>Structure of <a href="/wiki/Bis(cyclooctadiene)nickel(0)" title="Bis(cyclooctadiene)nickel(0)">bis(cyclooctadiene)nickel(0)</a>, a metal–alkene complex</figcaption></figure></dd></dl> <p>In <a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">transition metal alkene complexes</a>, alkenes serve as ligands for metals.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In this case, the π electron density is donated<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (September 2023)">clarification needed</span></a></i>]</sup> to the metal d orbitals. The stronger the donation is, the stronger the <a href="/wiki/Back_bonding" class="mw-redirect" title="Back bonding">back bonding</a> from the metal d orbital to π* anti-bonding orbital of the alkene. This effect lowers the bond order of the alkene and increases the C-C <a href="/wiki/Bond_length" title="Bond length">bond length</a>. One example is the complex <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">PtCl<sub class="template-chem2-sub">3</sub>(C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>)]<sup class="template-chem2-sup">−</sup></span>. These complexes are related to the mechanisms of metal-catalyzed reactions of unsaturated hydrocarbons.<sup id="cite_ref-JFH_23-1" class="reference"><a href="#cite_note-JFH-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reaction_overview">Reaction overview</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=19" title="Edit section: Reaction overview"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable" style="background-color:white;float: center; border-collapse: collapse; margin: 0em 1em;" border="1" cellpadding="2" cellspacing="0"> <tbody><tr> <th width="200px">Reaction name</th> <th>Product</th> <th class="unsortable">Comment </th></tr> <tr> <td valign="top"><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> </td> <td valign="top">alkanes </td> <td>addition of hydrogen </td></tr> <tr> <td><a href="/w/index.php?title=Hydroalkenylation&action=edit&redlink=1" class="new" title="Hydroalkenylation (page does not exist)">Hydroalkenylation</a> </td> <td>alkenes </td> <td>hydrometalation / insertion / beta-elimination by metal catalyst </td></tr> <tr> <td valign="top"><a href="/wiki/Halogen_addition_reaction" title="Halogen addition reaction">Halogen addition reaction</a> </td> <td valign="top">1,2-dihalide </td> <td>electrophilic addition of halogens </td></tr> <tr> <td valign="top"><a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a> (<a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov</a>) </td> <td valign="top">haloalkanes </td> <td>addition of hydrohalic acids </td></tr> <tr> <td valign="top">Anti-Markovnikov <a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">hydrohalogenation</a> </td> <td valign="top">haloalkanes </td> <td>free radicals mediated addition of hydrohalic acids </td></tr> <tr> <td valign="top"><a href="/wiki/Hydroamination" title="Hydroamination">Hydroamination</a> </td> <td valign="top">amines </td> <td>addition of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">N−H</span> bond across <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C−C</span> double bond </td></tr> <tr> <td valign="top"><a href="/wiki/Hydroformylation" title="Hydroformylation">Hydroformylation</a> </td> <td valign="top">aldehydes </td> <td>industrial process, addition of CO and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub></span> </td></tr> <tr> <td valign="top"><a href="/wiki/Hydrocarboxylation" class="mw-redirect" title="Hydrocarboxylation">Hydrocarboxylation</a> and <a href="/wiki/Koch_reaction" title="Koch reaction">Koch reaction</a> </td> <td valign="top">carboxylic acid </td> <td>industrial process, addition of CO and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span>. </td></tr> <tr> <td valign="top"><a href="/wiki/Carboalkoxylation" title="Carboalkoxylation">Carboalkoxylation</a> </td> <td valign="top">ester </td> <td>industrial process, addition of CO and alcohol. </td></tr> <tr> <td valign="top"><a href="/wiki/Alkylation" title="Alkylation">alkylation</a> </td> <td valign="top">ester </td> <td>industrial process: alkene alkylating carboxylic acid with <a href="/wiki/Silicotungstic_acid" title="Silicotungstic acid">silicotungstic acid</a> the catalyst. </td></tr> <tr> <td valign="top"><a href="/wiki/Sharpless_bishydroxylation" class="mw-redirect" title="Sharpless bishydroxylation">Sharpless bishydroxylation</a> </td> <td valign="top">diols </td> <td>oxidation, reagent: osmium tetroxide, chiral ligand </td></tr> <tr> <td valign="top"><a href="/wiki/Woodward_cis-hydroxylation" title="Woodward cis-hydroxylation">Woodward <i>cis</i>-hydroxylation</a> </td> <td valign="top">diols </td> <td>oxidation, reagents: iodine, silver acetate </td></tr> <tr> <td valign="top"><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a> </td> <td valign="top">aldehydes or ketones </td> <td>reagent: ozone </td></tr> <tr> <td><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a> </td> <td>alkenes </td> <td>two alkenes rearrange to form two new alkenes </td></tr> <tr> <td><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a> </td> <td>cyclohexenes </td> <td>cycloaddition with a diene </td></tr> <tr> <td><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a> </td> <td>cyclopentenones </td> <td>cycloaddition with an alkyne and CO </td></tr> <tr> <td><a href="/wiki/Hydroboration%E2%80%93oxidation" class="mw-redirect" title="Hydroboration–oxidation">Hydroboration–oxidation</a> </td> <td>alcohols </td> <td>reagents: borane, then a peroxide </td></tr> <tr> <td><a href="/wiki/Oxymercuration-reduction" class="mw-redirect" title="Oxymercuration-reduction">Oxymercuration-reduction</a> </td> <td>alcohols </td> <td>electrophilic addition of mercuric acetate, then reduction </td></tr> <tr> <td><a href="/wiki/Prins_reaction" title="Prins reaction">Prins reaction</a> </td> <td>1,3-diols </td> <td>electrophilic addition with aldehyde or ketone </td></tr> <tr> <td><a href="/wiki/Paterno%E2%80%93B%C3%BCchi_reaction" class="mw-redirect" title="Paterno–Büchi reaction">Paterno–Büchi reaction</a> </td> <td>oxetanes </td> <td>photochemical reaction with aldehyde or ketone </td></tr> <tr> <td><a href="/wiki/Epoxidation" class="mw-redirect" title="Epoxidation">Epoxidation</a> </td> <td>epoxide </td> <td>electrophilic addition of a peroxide </td></tr> <tr> <td><a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a> </td> <td>cyclopropanes </td> <td>addition of carbenes or carbenoids </td></tr> <tr> <td><a href="/wiki/Hydroacylation" title="Hydroacylation">Hydroacylation</a> </td> <td>ketones </td> <td>oxidative addition / reductive elimination by metal catalyst </td></tr> <tr> <td><a href="/wiki/Hydrophosphination" title="Hydrophosphination">Hydrophosphination</a> </td> <td>phosphines </td> <td> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=20" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial_methods">Industrial methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=21" title="Edit section: Industrial methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes are produced by hydrocarbon <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a>. Raw materials are mostly <a href="/wiki/Natural-gas_condensate" title="Natural-gas condensate">natural-gas condensate</a> components (principally ethane and propane) in the US and Mideast and <a href="/wiki/Naphtha" title="Naphtha">naphtha</a> in Europe and Asia. Alkanes are broken apart at high temperatures, often in the presence of a <a href="/wiki/Zeolite" title="Zeolite">zeolite</a> catalyst, to produce a mixture of primarily aliphatic alkenes and lower molecular weight alkanes. The mixture is feedstock and temperature dependent, and separated by fractional distillation. This is mainly used for the manufacture of small alkenes (up to six carbons).<sup id="cite_ref-Wade2_25-0" class="reference"><a href="#cite_note-Wade2-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:OctaneCracking.svg" class="mw-file-description" title="Cracking of n-octane to give pentane and propene"><img alt="Cracking of n-octane to give pentane and propene" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/OctaneCracking.svg/500px-OctaneCracking.svg.png" decoding="async" width="500" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/OctaneCracking.svg/750px-OctaneCracking.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/OctaneCracking.svg/1000px-OctaneCracking.svg.png 2x" data-file-width="512" data-file-height="49" /></a><figcaption>Cracking of <i>n</i>-octane to give pentane and propene</figcaption></figure> <p>Related to this is catalytic <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a>, where an alkane loses hydrogen at high temperatures to produce a corresponding alkene.<sup id="cite_ref-Wade_1-2" class="reference"><a href="#cite_note-Wade-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> This is the reverse of the <a href="/wiki/Catalytic_hydrogenation" class="mw-redirect" title="Catalytic hydrogenation">catalytic hydrogenation</a> of alkenes. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:ButaneDehydrogenation.svg" class="mw-file-description" title="Dehydrogenation of butane to give butadiene and isomers of butene"><img alt="Dehydrogenation of butane to give butadiene and isomers of butene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/ButaneDehydrogenation.svg/600px-ButaneDehydrogenation.svg.png" decoding="async" width="600" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/ButaneDehydrogenation.svg/900px-ButaneDehydrogenation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/ButaneDehydrogenation.svg/1200px-ButaneDehydrogenation.svg.png 2x" data-file-width="512" data-file-height="50" /></a><figcaption>Dehydrogenation of butane to give butadiene and isomers of butene</figcaption></figure> <p>This process is also known as <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">reforming</a>. Both processes are endothermic and are driven towards the alkene at high temperatures by <a href="/wiki/Entropy" title="Entropy">entropy</a>. </p><p><a href="/wiki/Catalytic" class="mw-redirect" title="Catalytic">Catalytic</a> synthesis of higher α-alkenes (of the type RCH=CH<sub>2</sub>) can also be achieved by a reaction of ethylene with the <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compound</a> <a href="/wiki/Triethylaluminium" title="Triethylaluminium">triethylaluminium</a> in the presence of <a href="/wiki/Nickel" title="Nickel">nickel</a>, <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>, or <a href="/wiki/Platinum" title="Platinum">platinum</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Elimination_reactions">Elimination reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=22" title="Edit section: Elimination reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>One of the principal methods for alkene synthesis in the laboratory is the <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reaction</a> of alkyl halides, alcohols, and similar compounds. Most common is the β-elimination via the E2 or E1 mechanism.<sup id="cite_ref-PataiBook1964_26-0" class="reference"><a href="#cite_note-PataiBook1964-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> A commercially significant example is the production of <a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a>. </p><p>The E2 mechanism provides a more reliable β-elimination method than E1 for most alkene syntheses. Most E2 eliminations start with an alkyl halide or alkyl sulfonate ester (such as a <a href="/wiki/Tosylate" class="mw-redirect" title="Tosylate">tosylate</a> or <a href="/wiki/Triflate" title="Triflate">triflate</a>). When an alkyl halide is used, the reaction is called a <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a>. For unsymmetrical products, the more substituted alkenes (those with fewer hydrogens attached to the C=C) tend to predominate (see <a href="/wiki/Zaitsev%27s_rule" class="mw-redirect" title="Zaitsev's rule">Zaitsev's rule</a>). Two common methods of elimination reactions are dehydrohalogenation of alkyl halides and dehydration of alcohols. A typical example is shown below; note that if possible, the H is <i>anti</i> to the leaving group, even though this leads to the less stable <i>Z</i>-isomer.<sup id="cite_ref-Cram1956_27-0" class="reference"><a href="#cite_note-Cram1956-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:E2EliminationExample.png" class="mw-file-description" title="An example of an E2 Elimination"><img alt="An example of an E2 Elimination" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/E2EliminationExample.png/500px-E2EliminationExample.png" decoding="async" width="500" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/E2EliminationExample.png/750px-E2EliminationExample.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/E2EliminationExample.png/1000px-E2EliminationExample.png 2x" data-file-width="1607" data-file-height="365" /></a><figcaption>An example of an E2 Elimination</figcaption></figure> <p>Alkenes can be synthesized from alcohols via <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydration</a>, in which case water is lost via the E1 mechanism. For example, the dehydration of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> produces ethylene: </p> <dl><dd>CH<sub>3</sub>CH<sub>2</sub>OH → H<sub>2</sub>C=CH<sub>2</sub> + H<sub>2</sub>O</dd></dl> <p>An alcohol may also be converted to a better leaving group (e.g., <a href="/wiki/Xanthate" title="Xanthate">xanthate</a>), so as to allow a milder <i>syn</i>-elimination such as the <a href="/wiki/Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a> and the <a href="/wiki/Grieco_elimination" title="Grieco elimination">Grieco elimination</a>. Related reactions include eliminations by β-haloethers (the <a href="/wiki/Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a>) and esters (<a href="/wiki/Ester_pyrolysis" title="Ester pyrolysis">ester pyrolysis</a>). A <a href="/wiki/Thioketone" title="Thioketone">thioketone</a> and a <a href="/wiki/Phosphite_ester" title="Phosphite ester">phosphite ester</a> combined (the <a href="/wiki/Corey-Winter_olefination" class="mw-redirect" title="Corey-Winter olefination">Corey-Winter olefination</a>) or <a href="/wiki/Diphosphorus_tetraiodide" title="Diphosphorus tetraiodide">diphosphorus tetraiodide</a> will deoxygenate <a href="/wiki/Glycol" class="mw-redirect" title="Glycol">glycols</a> to alkenes. </p><p>Alkenes can be prepared indirectly from alkyl <a href="/wiki/Amine" title="Amine">amines</a>. The amine or ammonia is not a suitable leaving group, so the amine is first either <a href="/wiki/Alkylation" title="Alkylation">alkylated</a> (as in the <a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a>) or oxidized to an <a href="/wiki/Amine_oxide" title="Amine oxide">amine oxide</a> (the <a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a>) to render a smooth elimination possible. The Cope reaction is a <i>syn</i>-elimination that occurs at or below 150 °C, for example:<sup id="cite_ref-CopeElimination1973_28-0" class="reference"><a href="#cite_note-CopeElimination1973-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:CopeEliminationExample.svg" class="mw-file-description" title="Synthesis of cyclooctene via Cope elimination"><img alt="Synthesis of cyclooctene via Cope elimination" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/CopeEliminationExample.svg/300px-CopeEliminationExample.svg.png" decoding="async" width="300" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/CopeEliminationExample.svg/450px-CopeEliminationExample.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/CopeEliminationExample.svg/600px-CopeEliminationExample.svg.png 2x" data-file-width="512" data-file-height="131" /></a><figcaption>Synthesis of cyclooctene via Cope elimination</figcaption></figure> <p>The Hofmann elimination is unusual in that the <i>less</i> substituted (non-<a href="/wiki/Zaitsev%27s_rule" class="mw-redirect" title="Zaitsev's rule">Zaitsev</a>) alkene is usually the major product. </p><p>Alkenes are generated from α-halo<a href="/wiki/Sulfone" title="Sulfone">sulfones</a> in the <a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a>, via a three-membered ring sulfone intermediate. </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis_from_carbonyl_compounds">Synthesis from carbonyl compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=23" title="Edit section: Synthesis from carbonyl compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Another important class of methods for alkene synthesis involves construction of a new carbon–carbon double bond by coupling or condensation of a carbonyl compound (such as an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> or <a href="/wiki/Ketone" title="Ketone">ketone</a>) to a <a href="/wiki/Carbanion" title="Carbanion">carbanion</a> or its equivalent. Pre-eminent is the <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a>. Knoevenagel condensations are a related class of reactions that convert carbonyls into alkenes.Well-known methods are called <i>olefinations</i>. The <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> is illustrative, but other related methods are known, including the <a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a>. </p><p>The Wittig reaction involves reaction of an aldehyde or ketone with a <a href="/wiki/Wittig_reagent" class="mw-redirect" title="Wittig reagent">Wittig reagent</a> (or phosphorane) of the type Ph<sub>3</sub>P=CHR to produce an alkene and <a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">Ph<sub>3</sub>P=O</a>. The Wittig reagent is itself prepared easily from <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a> and an alkyl halide.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Wittig_reaction_example.svg" class="mw-file-description" title="A typical example of the Wittig reaction"><img alt="A typical example of the Wittig reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Wittig_reaction_example.svg/500px-Wittig_reaction_example.svg.png" decoding="async" width="350" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Wittig_reaction_example.svg/960px-Wittig_reaction_example.svg.png 1.5x" data-file-width="1280" data-file-height="495" /></a><figcaption>A typical example of the Wittig reaction</figcaption></figure> <p>Related to the Wittig reaction is the <a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a>, which uses silicon-based reagents in place of the phosphorane. This reaction allows for the selection of <i>E</i>- or <i>Z</i>-products. If an <i>E</i>-product is desired, another alternative is the <a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a>, which uses the carbanion generated from a <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> <a href="/wiki/Sulfone" title="Sulfone">sulfone</a>. The <a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a> based on an organochromium intermediate also delivers E-products. A titanium compound, <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a>, is useful for the synthesis of methylene compounds; in this case, even esters and amides react. </p><p>A pair of ketones or aldehydes can be <a href="/wiki/Deoxygenation" title="Deoxygenation">deoxygenated</a> to generate an alkene. Symmetrical alkenes can be prepared from a single aldehyde or ketone coupling with itself, using <a href="/wiki/Titanium" title="Titanium">titanium</a> metal reduction (the <a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a>). If different ketones are to be coupled, a more complicated method is required, such as the <a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a>. </p><p>A single ketone can also be converted to the corresponding alkene via its tosylhydrazone, using <a href="/wiki/Sodium_methoxide" title="Sodium methoxide">sodium methoxide</a> (the <a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a>) or an alkyllithium (the <a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a>). </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis_from_alkenes">Synthesis from alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=24" title="Edit section: Synthesis from alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The formation of longer alkenes via the step-wise polymerisation of smaller ones is appealing, as <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (the smallest alkene) is both inexpensive and readily available, with hundreds of millions of tonnes produced annually. The <a href="/wiki/Ziegler%E2%80%93Natta_process" class="mw-redirect" title="Ziegler–Natta process">Ziegler–Natta process</a> allows for the formation of very long chains, for instance those used for <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a>. Where shorter chains are wanted, as they for the production of <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>, then processes incorporating a <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a> step, such as the <a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a> are important. </p><p>Olefin metathesis is also used commercially for the interconversion of ethylene and 2-butene to propylene. Rhenium- and molybdenum-containing <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">heterogeneous catalysis</a> are used in this process:<sup id="cite_ref-KO_30-0" class="reference"><a href="#cite_note-KO-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CH<sub>2</sub>=CH<sub>2</sub> + CH<sub>3</sub>CH=CHCH<sub>3</sub> → 2 CH<sub>2</sub>=CHCH<sub>3</sub></dd></dl> <p>Transition metal catalyzed <a href="/wiki/Hydrovinylation" title="Hydrovinylation">hydrovinylation</a> is another important alkene synthesis process starting from alkene itself.<sup id="cite_ref-Vogt2010_31-0" class="reference"><a href="#cite_note-Vogt2010-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> It involves the addition of a hydrogen and a vinyl group (or an alkenyl group) across a double bond. </p> <div class="mw-heading mw-heading3"><h3 id="From_alkynes">From alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=25" title="Edit section: From alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reduction of <a href="/wiki/Alkyne" title="Alkyne">alkynes</a> is a useful method for the <a href="/wiki/Stereoselectivity" title="Stereoselectivity">stereoselective</a> synthesis of disubstituted alkenes. If the <i>cis</i>-alkene is desired, <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> in the presence of <a href="/wiki/Lindlar%27s_catalyst" class="mw-redirect" title="Lindlar's catalyst">Lindlar's catalyst</a> (a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead) is commonly used, though hydroboration followed by hydrolysis provides an alternative approach. Reduction of the alkyne by <a href="/wiki/Sodium" title="Sodium">sodium</a> metal in liquid <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> gives the <i>trans</i>-alkene.<sup id="cite_ref-ZweifelNantz_32-0" class="reference"><a href="#cite_note-ZweifelNantz-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:AlkyneToAlkene.png" class="mw-file-description" title="Synthesis of cis- and trans-alkenes from alkynes"><img alt="Synthesis of cis- and trans-alkenes from alkynes" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/AlkyneToAlkene.png/600px-AlkyneToAlkene.png" decoding="async" width="600" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/AlkyneToAlkene.png/900px-AlkyneToAlkene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/AlkyneToAlkene.png/1200px-AlkyneToAlkene.png 2x" data-file-width="3099" data-file-height="446" /></a><figcaption>Synthesis of <i>cis</i>- and <i>trans</i>-alkenes from alkynes</figcaption></figure> <p>For the preparation multisubstituted alkenes, <a href="/wiki/Carbometalation" title="Carbometalation">carbometalation</a> of alkynes can give rise to a large variety of alkene derivatives. </p> <div class="mw-heading mw-heading3"><h3 id="Rearrangements_and_related_reactions">Rearrangements and related reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=26" title="Edit section: Rearrangements and related reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes can be synthesized from other alkenes via <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reactions</a>. Besides <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a> (described <a href="#Synthesis_from_alkenes">above</a>), many <a href="/wiki/Pericyclic_reaction" title="Pericyclic reaction">pericyclic reactions</a> can be used such as the <a href="/wiki/Ene_reaction" title="Ene reaction">ene reaction</a> and the <a href="/wiki/Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:3,3copeexpansion.svg" class="mw-file-description" title="Cope rearrangement of divinylcyclobutane to cyclooctadiene"><img alt="Cope rearrangement of divinylcyclobutane to cyclooctadiene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/3%2C3copeexpansion.svg/180px-3%2C3copeexpansion.svg.png" decoding="async" width="180" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/3%2C3copeexpansion.svg/270px-3%2C3copeexpansion.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/3%2C3copeexpansion.svg/360px-3%2C3copeexpansion.svg.png 2x" data-file-width="251" data-file-height="108" /></a><figcaption>Cope rearrangement of divinylcyclobutane to cyclooctadiene</figcaption></figure> <p>In the <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a>, a <a href="/wiki/Cyclohexene" title="Cyclohexene">cyclohexene</a> derivative is prepared from a diene and a reactive or electron-deficient alkene. </p><p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Application">Application</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=27" title="Edit section: Application"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unsaturated hydrocarbons are widely used to produce plastics, medicines, and other useful materials. </p> <table class="wikitable"> <caption> </caption> <tbody><tr> <th>Name </th> <th>Structure </th> <th>Use </th></tr> <tr> <td><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a> </td> <td><figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Ethene_structural.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/60px-Ethene_structural.svg.png" decoding="async" width="60" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/120px-Ethene_structural.svg.png 1.5x" data-file-width="170" data-file-height="160" /></a><figcaption></figcaption></figure> </td> <td> <ul><li>Monomers for synthesizing <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a></li></ul> </td></tr> <tr> <td><a href="/wiki/Butadiene" title="Butadiene">1,3-butadiene</a> </td> <td><figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:1,3-butadiene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/100px-1%2C3-butadiene.svg.png" decoding="async" width="100" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/150px-1%2C3-butadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/200px-1%2C3-butadiene.svg.png 2x" data-file-width="1024" data-file-height="800" /></a><figcaption></figcaption></figure> </td> <td> <ul><li>For manufacturing <a href="/wiki/Synthetic_rubber" title="Synthetic rubber">synthetic rubber</a></li></ul> </td></tr> <tr> <td><a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a> </td> <td><figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Vinyl_chloride.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Vinyl_chloride.svg/60px-Vinyl_chloride.svg.png" decoding="async" width="60" height="29" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Vinyl_chloride.svg/90px-Vinyl_chloride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Vinyl_chloride.svg/120px-Vinyl_chloride.svg.png 2x" data-file-width="165" data-file-height="80" /></a><figcaption></figcaption></figure> </td> <td> <ul><li>Precursor to <a href="/wiki/PVC" class="mw-redirect" title="PVC">PVC</a></li></ul> </td></tr> <tr> <td><a href="/wiki/Styrene" title="Styrene">styrene</a> </td> <td><figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Styrene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Styrene.svg/90px-Styrene.svg.png" decoding="async" width="90" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Styrene.svg/135px-Styrene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Styrene.svg/180px-Styrene.svg.png 2x" data-file-width="109" data-file-height="73" /></a><figcaption></figcaption></figure> </td> <td> <ul><li>precursor to <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a></li></ul> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=28" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes are prevalent in nature. Plants are the main natural source of alkenes in the form of <a href="/wiki/Terpene" title="Terpene">terpenes</a>.<sup id="cite_ref-Ninkuu_2021_33-0" class="reference"><a href="#cite_note-Ninkuu_2021-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Many of the most vivid natural pigments are terpenes; e.g. <a href="/wiki/Lycopene" title="Lycopene">lycopene</a> (red in tomatoes), <a href="/wiki/Carotene" title="Carotene">carotene</a> (orange in carrots), and <a href="/wiki/Xanthophyll" title="Xanthophyll">xanthophylls</a> (yellow in egg yolk). The simplest of all alkenes, <a href="/wiki/Ethylene_(plant_hormone)" title="Ethylene (plant hormone)">ethylene</a> is a <a href="/wiki/Signaling_molecule" class="mw-redirect" title="Signaling molecule">signaling molecule</a> that influences the ripening of plants. </p><p>The <a href="/wiki/Curiosity_(rover)" title="Curiosity (rover)">Curiosity</a> rover discovered on Mars long chain alkanes with up to 12 consecutive carbon atoms. They could be derived from either abiotic or biological sources.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Selected unsaturated compounds in nature</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Limonene-2D-skeletal.svg" class="mw-file-description" title="Limonene, a monoterpene."><img alt="Limonene, a monoterpene." src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Limonene-2D-skeletal.svg/60px-Limonene-2D-skeletal.svg.png" decoding="async" width="49" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Limonene-2D-skeletal.svg/120px-Limonene-2D-skeletal.svg.png 1.5x" data-file-width="769" data-file-height="1881" /></a></span></div> <div class="gallerytext"><a href="/wiki/Limonene" title="Limonene">Limonene</a>, a <a href="/wiki/Monoterpene" title="Monoterpene">monoterpene</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-Caryophyllen.svg" class="mw-file-description" title="Humulene, a sesquiterpene."><img alt="Humulene, a sesquiterpene." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Alpha-Caryophyllen.svg/120px-Alpha-Caryophyllen.svg.png" decoding="async" width="120" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Alpha-Caryophyllen.svg/180px-Alpha-Caryophyllen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Alpha-Caryophyllen.svg/240px-Alpha-Caryophyllen.svg.png 2x" data-file-width="233" data-file-height="218" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Humulene" title="Humulene">Humulene</a>, a <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpene</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Taxadiene.svg" class="mw-file-description" title="Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent."><img alt="Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/120px-Taxadiene.svg.png" decoding="async" width="120" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/180px-Taxadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/240px-Taxadiene.svg.png 2x" data-file-width="512" data-file-height="327" /></a></span></div> <div class="gallerytext"><a href="/wiki/Taxadiene" title="Taxadiene">Taxadiene</a>, a <a href="/wiki/Diterpene" title="Diterpene">diterpene</a>, precursor to the diterpenoid <a href="/wiki/Taxol" class="mw-redirect" title="Taxol">taxol</a>, an anticancer agent.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Squalene.svg" class="mw-file-description" title="Squalene, a triterpene and universal precursor to natural steroids."><img alt="Squalene, a triterpene and universal precursor to natural steroids." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Squalene.svg/120px-Squalene.svg.png" decoding="async" width="120" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Squalene.svg/250px-Squalene.svg.png 1.5x" data-file-width="420" data-file-height="70" /></a></span></div> <div class="gallerytext"><a href="/wiki/Squalene" title="Squalene">Squalene</a>, a <a href="/wiki/Triterpene" title="Triterpene">triterpene</a> and universal precursor to natural <a href="/wiki/Steroid" title="Steroid">steroids</a>.</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="IUPAC_Nomenclature">IUPAC Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=29" title="Edit section: IUPAC Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the nomenclature is not followed widely, according to IUPAC, an alkene is an acyclic hydrocarbon with just one double bond between carbon atoms.<sup id="cite_ref-PAC1995.alkenes_2-1" class="reference"><a href="#cite_note-PAC1995.alkenes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Olefins comprise a larger collection of cyclic and acyclic alkenes as well as dienes and polyenes.<sup id="cite_ref-PAC1995.olefins_3-2" class="reference"><a href="#cite_note-PAC1995.olefins-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>To form the root of the <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC names</a> for straight-chain alkenes, change the <i>-an-</i> infix of the parent to <i>-en-</i>. For example, <b>CH<sub>3</sub>-CH<sub>3</sub></b> is the <a href="/wiki/Alkane" title="Alkane">alkane</a> <i>ethANe</i>. The name of <b>CH<sub>2</sub>=CH<sub>2</sub></b> is therefore <i>ethENe</i>. </p><p>For straight-chain alkenes with 4 or more carbon atoms, that name does not completely identify the compound. For those cases, and for branched acyclic alkenes, the following rules apply: </p> <ol><li>Find the longest carbon chain in the molecule. If that chain does not contain the double bond, name the compound according to the alkane naming rules. Otherwise:</li> <li>Number the carbons in that chain starting from the end that is closest to the double bond.</li> <li>Define the location <i>k</i> of the double bond as being the number of its first carbon.</li> <li>Name the side groups (other than hydrogen) according to the appropriate rules.</li> <li>Define the position of each side group as the number of the chain carbon it is attached to.</li> <li>Write the position and name of each side group.</li> <li>Write the names of the alkane with the same chain, replacing the "-ane" suffix by "<i>k</i>-ene".</li></ol> <p>The position of the double bond is often inserted before the name of the chain (e.g. "2-pentene"), rather than before the suffix ("pent-2-ene"). </p><p>The positions need not be indicated if they are unique. Note that the double bond may imply a different chain numbering than that used for the corresponding alkane: <span class="chemf nowrap">(H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>C)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>C–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span> is "2,2-dimethyl pentane", whereas <span class="chemf nowrap">(H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>C)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>C–<span class="chemf nowrap">CH</span>=<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> is "3,3-dimethyl 1-pentene". </p><p>More complex rules apply for polyenes and <a href="/wiki/Cycloalkene" title="Cycloalkene">cycloalkenes</a>.<sup id="cite_ref-PAC1995_4-1" class="reference"><a href="#cite_note-PAC1995-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Alkene_nomenclature.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Alkene_nomenclature.svg/550px-Alkene_nomenclature.svg.png" decoding="async" width="550" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Alkene_nomenclature.svg/825px-Alkene_nomenclature.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Alkene_nomenclature.svg/1100px-Alkene_nomenclature.svg.png 2x" data-file-width="1360" data-file-height="251" /></a><figcaption>Naming substituted hex-1-enes</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Cis–trans_isomerism"><span id="Cis.E2.80.93trans_isomerism"></span><i>Cis</i>–<i>trans</i> isomerism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=30" title="Edit section: Cis–trans isomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If the double bond of an acyclic mono-ene is not the first bond of the chain, the name as constructed above still does not completely identify the compound, because of <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i>–<i>trans</i> isomerism</a>. Then one must specify whether the two single C–C bonds adjacent to the double bond are on the same side of its plane, or on opposite sides. For monoalkenes, the configuration is often indicated by the prefixes <i>cis</i>- (from <a href="/wiki/Latin" title="Latin">Latin</a> "on this side of") or <i>trans</i>- ("across", "on the other side of") before the name, respectively; as in <i>cis</i>-2-pentene or <i>trans</i>-2-butene. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Cis-trans_example.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/330px-Cis-trans_example.svg.png" decoding="async" width="300" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/500px-Cis-trans_example.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/600px-Cis-trans_example.svg.png 2x" data-file-width="540" data-file-height="230" /></a><figcaption>The difference between <i>cis-</i> and <i>trans-</i> isomers</figcaption></figure> <p>More generally, <i>cis</i>–<i>trans</i> isomerism will exist if each of the two carbons of in the double bond has two different atoms or groups attached to it. Accounting for these cases, the IUPAC recommends the more general <a href="/wiki/E%E2%80%93Z_notation" title="E–Z notation">E–Z notation</a>, instead of the <i>cis</i> and <i>trans</i> prefixes. This notation considers the group with highest <a href="/wiki/Cahn-Ingold-Prelog_priority_rule" class="mw-redirect" title="Cahn-Ingold-Prelog priority rule">CIP priority</a> in each of the two carbons. If these two groups are on opposite sides of the double bond's plane, the configuration is labeled <i>E</i> (from the <a href="/wiki/German_language" title="German language">German</a> <i>entgegen</i> meaning "opposite"); if they are on the same side, it is labeled <i>Z</i> (from German <i>zusammen</i>, "together"). This labeling may be taught with mnemonic "<i>Z</i> means 'on ze zame zide'".<sup id="cite_ref-murr2014_35-0" class="reference"><a href="#cite_note-murr2014-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:EZalkenes2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/EZalkenes2.png/500px-EZalkenes2.png" decoding="async" width="400" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/EZalkenes2.png/960px-EZalkenes2.png 1.5x" data-file-width="1683" data-file-height="576" /></a><figcaption>The difference between <i>E</i> and <i>Z</i> isomers</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Groups_containing_C=C_double_bonds"><span id="Groups_containing_C.3DC_double_bonds"></span>Groups containing C=C double bonds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=31" title="Edit section: Groups containing C=C double bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>IUPAC recognizes two names for hydrocarbon groups containing carbon–carbon double bonds, the <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl group</a> and the <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a> group.<sup id="cite_ref-PAC1995_4-2" class="reference"><a href="#cite_note-PAC1995-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:AlkenylGroups.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/AlkenylGroups.png/250px-AlkenylGroups.png" decoding="async" width="200" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/AlkenylGroups.png/330px-AlkenylGroups.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/AlkenylGroups.png/500px-AlkenylGroups.png 2x" data-file-width="1146" data-file-height="314" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=32" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wiktionary-logo-en-v2.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/120px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/alkene" class="extiw" title="wiktionary:Special:Search/alkene">alkene</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735" /><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wikiquote-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></a></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Alkene" class="extiw" title="q:Special:Search/Alkene">Alkene</a></b></i>.</div></div> </div> <ul><li><a href="/wiki/Alpha-olefin" class="mw-redirect" title="Alpha-olefin">Alpha-olefin</a></li> <li><a href="/wiki/Annulene" title="Annulene">Annulene</a></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbon</a> ("Arene")</li> <li><a href="/wiki/Dendralene" title="Dendralene">Dendralene</a></li> <li><a href="/wiki/Nitroalkene" title="Nitroalkene">Nitroalkene</a></li> <li><a href="/wiki/Radialene" title="Radialene">Radialene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Nomenclature_links">Nomenclature links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=33" title="Edit section: Nomenclature links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_53.htm">Rule A-3. Unsaturated Compounds and Univalent Radicals</a> <a href="/wiki/IUPAC_Color_Books#Blue_Book" title="IUPAC Color Books">IUPAC Blue Book</a>.</li> <li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_78.htm">Rule A-4. Bivalent and Multivalent Radicals</a> IUPAC Blue Book.</li> <li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_60.htm">Rules A-11.3, A-11.4, A-11.5 Unsaturated monocyclic hydrocarbons and substituents</a> IUPAC Blue Book.</li> <li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_73.htm">Rule A-23. Hydrogenated Compounds of Fused Polycyclic Hydrocarbons</a> IUPAC Blue Book.</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkene&action=edit&section=34" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Wade-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wade_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wade_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Wade_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFWade2006" class="citation book cs1">Wade, L.G. (2006). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00lgwa_203"><i>Organic Chemistry</i></a></span> (6th ed.). Pearson <a href="/wiki/Prentice_Hall" title="Prentice Hall">Prentice Hall</a>. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00lgwa_203/page/n322">279</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4058-5345-3" title="Special:BookSources/978-1-4058-5345-3"><bdi>978-1-4058-5345-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=279&rft.edition=6th&rft.pub=Pearson+Prentice+Hall&rft.date=2006&rft.isbn=978-1-4058-5345-3&rft.aulast=Wade&rft.aufirst=L.G.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganicchemistry00lgwa_203&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-PAC1995.alkenes-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-PAC1995.alkenes_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PAC1995.alkenes_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00224.html">alkenes</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00224">10.1351/goldbook.A00224</a></span> </li> <li id="cite_note-PAC1995.olefins-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-PAC1995.olefins_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PAC1995.olefins_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PAC1995.olefins_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/O04281.html">olefins</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.O04281">10.1351/goldbook.O04281</a></span> </li> <li id="cite_note-PAC1995-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-PAC1995_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PAC1995_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PAC1995_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMossSmithTavernier1995" class="citation journal cs1">Moss, G. P.; Smith, P. A. S.; Tavernier, D. (1995). <a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac199567081307">"Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure (IUPAC Recommendations 1995)"</a>. <i><a href="/wiki/Pure_and_Applied_Chemistry" title="Pure and Applied Chemistry">Pure and Applied Chemistry</a></i>. <b>67</b> (<span class="nowrap">8–</span>9): <span class="nowrap">1307–</span>75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac199567081307">10.1351/pac199567081307</a></span>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:95004254">95004254</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+and+Applied+Chemistry&rft.atitle=Glossary+of+Class+Names+of+Organic+Compounds+and+Reactive+Intermediates+Based+on+Structure+%28IUPAC+Recommendations+1995%29&rft.volume=67&rft.issue=%3Cspan+class%3D%22nowrap%22%3E8%E2%80%93%3C%2Fspan%3E9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1307-%3C%2Fspan%3E75&rft.date=1995&rft_id=info%3Adoi%2F10.1351%2Fpac199567081307&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A95004254%23id-name%3DS2CID&rft.aulast=Moss&rft.aufirst=G.+P.&rft.au=Smith%2C+P.+A.+S.&rft.au=Tavernier%2C+D.&rft_id=https%3A%2F%2Fdoi.org%2F10.1351%252Fpac199567081307&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-cenews-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-cenews_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">"Production: Growth is the Norm". <i>Chemical and Engineering News</i>. <b>84</b> (28): <span class="nowrap">59–</span>236. 10 July 2006. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcen-v084n034.p059">10.1021/cen-v084n034.p059</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+and+Engineering+News&rft.atitle=Production%3A+Growth+is+the+Norm&rft.volume=84&rft.issue=28&rft.pages=%3Cspan+class%3D%22nowrap%22%3E59-%3C%2Fspan%3E236&rft.date=2006-07-10&rft_id=info%3Adoi%2F10.1021%2Fcen-v084n034.p059&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSloane_"A000631"" class="citation web cs1"><a href="/wiki/Neil_Sloane" title="Neil Sloane">Sloane, N. J. A.</a> (ed.). <a rel="nofollow" class="external text" href="https://oeis.org/A000631">"Sequence A000631 (Number of ethylene derivatives with n carbon atoms)"</a>. <i>The <a href="/wiki/On-Line_Encyclopedia_of_Integer_Sequences" title="On-Line Encyclopedia of Integer Sequences">On-Line Encyclopedia of Integer Sequences</a></i>. OEIS Foundation.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+On-Line+Encyclopedia+of+Integer+Sequences&rft.atitle=Sequence%26%23x20%3BA000631%26%23x20%3B%28Number+of+ethylene+derivatives+with+n+carbon+atoms%29&rft_id=https%3A%2F%2Foeis.org%2FA000631&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, p. 23, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.pages=23&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.aulast=Smith&rft.aufirst=Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-Bansal-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Bansal_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Bansal_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBansal1998" class="citation book cs1">Bansal, Raj K. (1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=bga3xjLVCo0C&pg=PT29">"Bredt's Rule"</a>. <i>Organic Reaction Mechanisms</i> (3rd ed.). <a href="/wiki/McGraw-Hill_Education" class="mw-redirect" title="McGraw-Hill Education">McGraw-Hill Education</a>. pp. <span class="nowrap">14–</span>16. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-07-462083-0" title="Special:BookSources/978-0-07-462083-0"><bdi>978-0-07-462083-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Bredt%27s+Rule&rft.btitle=Organic+Reaction+Mechanisms&rft.pages=%3Cspan+class%3D%22nowrap%22%3E14-%3C%2Fspan%3E16&rft.edition=3rd&rft.pub=McGraw-Hill+Education&rft.date=1998&rft.isbn=978-0-07-462083-0&rft.aulast=Bansal&rft.aufirst=Raj+K.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dbga3xjLVCo0C%26pg%3DPT29&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFawcett1950" class="citation journal cs1">Fawcett, Frank S. (1950). "Bredt's Rule of Double Bonds in Atomic-Bridged-Ring Structures". <i><a href="/wiki/Chem._Rev." class="mw-redirect" title="Chem. Rev.">Chem. Rev.</a></i> <b>47</b> (2): <span class="nowrap">219–</span>274. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60147a003">10.1021/cr60147a003</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24538877">24538877</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Rev.&rft.atitle=Bredt%27s+Rule+of+Double+Bonds+in+Atomic-Bridged-Ring+Structures&rft.volume=47&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E219-%3C%2Fspan%3E274&rft.date=1950&rft_id=info%3Adoi%2F10.1021%2Fcr60147a003&rft_id=info%3Apmid%2F24538877&rft.aulast=Fawcett&rft.aufirst=Frank+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1">"Bredt's Rule". <i>Comprehensive Organic Name Reactions and Reagents</i>. Vol. 116. 2010. pp. <span class="nowrap">525–</span>8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470638859.conrr116">10.1002/9780470638859.conrr116</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-63885-9" title="Special:BookSources/978-0-470-63885-9"><bdi>978-0-470-63885-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Bredt%27s+Rule&rft.btitle=Comprehensive+Organic+Name+Reactions+and+Reagents&rft.pages=%3Cspan+class%3D%22nowrap%22%3E525-%3C%2Fspan%3E8&rft.date=2010&rft_id=info%3Adoi%2F10.1002%2F9780470638859.conrr116&rft.isbn=978-0-470-63885-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDuanBlockLiConnelly2012" class="citation journal cs1">Duan, Xufang; Block, Eric; Li, Zhen; Connelly, Timothy; Zhang, Jian; Huang, Zhimin; Su, Xubo; Pan, Yi; Wu, Lifang (28 February 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295281">"Crucial role of copper in detection of metal-coordinating odorants"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>109</b> (9): <span class="nowrap">3492–</span>7. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2012PNAS..109.3492D">2012PNAS..109.3492D</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1111297109">10.1073/pnas.1111297109</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295281">3295281</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22328155">22328155</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Crucial+role+of+copper+in+detection+of+metal-coordinating+odorants&rft.volume=109&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3492-%3C%2Fspan%3E7&rft.date=2012-02-28&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3295281%23id-name%3DPMC&rft_id=info%3Apmid%2F22328155&rft_id=info%3Adoi%2F10.1073%2Fpnas.1111297109&rft_id=info%3Abibcode%2F2012PNAS..109.3492D&rft.aulast=Duan&rft.aufirst=Xufang&rft.au=Block%2C+Eric&rft.au=Li%2C+Zhen&rft.au=Connelly%2C+Timothy&rft.au=Zhang%2C+Jian&rft.au=Huang%2C+Zhimin&rft.au=Su%2C+Xubo&rft.au=Pan%2C+Yi&rft.au=Wu%2C+Lifang&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3295281&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-alkene_properties-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-alkene_properties_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNguyenClark2019" class="citation web cs1">Nguyen, Trung; Clark, Jim (23 April 2019). <a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alkenes/Properties_of_Alkenes/Physical_Properties_of_Alkenes">"Physical Properties of Alkenes"</a>. <i>Chemistry LibreTexts</i><span class="reference-accessdate">. Retrieved <span class="nowrap">27 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=Physical+Properties+of+Alkenes&rft.date=2019-04-23&rft.aulast=Nguyen&rft.aufirst=Trung&rft.au=Clark%2C+Jim&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_%28Organic_Chemistry%29%2FAlkenes%2FProperties_of_Alkenes%2FPhysical_Properties_of_Alkenes&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOphardt2003" class="citation web cs1">Ophardt, Charles (2003). <a rel="nofollow" class="external text" href="http://chemistry.elmhurst.edu/vchembook/501hcboilingpts.html">"Boiling Points and Structures of Hydrocarbons"</a>. <i>Virtual Chembook</i><span class="reference-accessdate">. Retrieved <span class="nowrap">27 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Virtual+Chembook&rft.atitle=Boiling+Points+and+Structures+of+Hydrocarbons&rft.date=2003&rft.aulast=Ophardt&rft.aufirst=Charles&rft_id=http%3A%2F%2Fchemistry.elmhurst.edu%2Fvchembook%2F501hcboilingpts.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHanson" class="citation web cs1">Hanson, John. <a rel="nofollow" class="external text" href="http://www2.ups.edu/faculty/hanson/Spectroscopy/NMR/HNMRshift.htm">"Overview of Chemical Shifts in H-NMR"</a>. <i>ups.edu</i><span class="reference-accessdate">. Retrieved <span class="nowrap">5 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ups.edu&rft.atitle=Overview+of+Chemical+Shifts+in+H-NMR&rft.aulast=Hanson&rft.aufirst=John&rft_id=http%3A%2F%2Fwww2.ups.edu%2Ffaculty%2Fhanson%2FSpectroscopy%2FNMR%2FHNMRshift.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-NMR_of_Alkenes-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-NMR_of_Alkenes_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NMR_of_Alkenes_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alkenes/Properties_of_Alkenes/Nuclear_Magnetic_Resonance_(NMR)_of_Alkenes">"Nuclear Magnetic Resonance (NMR) of Alkenes"</a>. <i>Chemistry LibreTexts</i>. 23 April 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">5 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=Nuclear+Magnetic+Resonance+%28NMR%29+of+Alkenes&rft.date=2019-04-23&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_%28Organic_Chemistry%29%2FAlkenes%2FProperties_of_Alkenes%2FNuclear_Magnetic_Resonance_%28NMR%29_of_Alkenes&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www2.ucdsb.on.ca/tiss/stretton/database/organic_thermo.htm">"Organic Compounds: Physical and Thermochemical Data"</a>. <i>ucdsb.on.ca</i><span class="reference-accessdate">. Retrieved <span class="nowrap">5 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ucdsb.on.ca&rft.atitle=Organic+Compounds%3A+Physical+and+Thermochemical+Data&rft_id=http%3A%2F%2Fwww2.ucdsb.on.ca%2Ftiss%2Fstretton%2Fdatabase%2Forganic_thermo.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShrinerHermannMorrillCurtin1997" class="citation book cs1">Shriner, R.L.; Hermann, C.K.F.; Morrill, T.C.; Curtin, D.Y.; Fuson, R.C. (1997). <i>The Systematic Identification of Organic Compounds</i>. Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-59748-1" title="Special:BookSources/0-471-59748-1"><bdi>0-471-59748-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Systematic+Identification+of+Organic+Compounds&rft.pub=Wiley&rft.date=1997&rft.isbn=0-471-59748-1&rft.aulast=Shriner&rft.aufirst=R.L.&rft.au=Hermann%2C+C.K.F.&rft.au=Morrill%2C+T.C.&rft.au=Curtin%2C+D.Y.&rft.au=Fuson%2C+R.C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.hach.com/asset-get.download.jsa?id=3980387617">"Bromine Number"</a>. <i>Hach company</i><span class="reference-accessdate">. Retrieved <span class="nowrap">5 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Hach+company&rft.atitle=Bromine+Number&rft_id=https%3A%2F%2Fwww.hach.com%2Fasset-get.download.jsa%3Fid%3D3980387617&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFClark2007" class="citation web cs1">Clark, Jim (November 2007). <a rel="nofollow" class="external text" href="https://www.chemguide.co.uk/physical/catalysis/hydrate.html">"The Mechanism for the Acid Catalysed Hydration of Ethene"</a>. <i>Chemguide</i><span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemguide&rft.atitle=The+Mechanism+for+the+Acid+Catalysed+Hydration+of+Ethene&rft.date=2007-11&rft.aulast=Clark&rft.aufirst=Jim&rft_id=https%3A%2F%2Fwww.chemguide.co.uk%2Fphysical%2Fcatalysis%2Fhydrate.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.aulast=Smith&rft.aufirst=Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBaptistaCadetMascioGhogare2017" class="citation journal cs1">Baptista, Maurício S.; Cadet, Jean; Mascio, Paolo Di; Ghogare, Ashwini A.; Greer, Alexander; Hamblin, Michael R.; Lorente, Carolina; Nunez, Silvia Cristina; Ribeiro, Martha Simões; Thomas, Andrés H.; Vignoni, Mariana; Yoshimura, Tania Mateus (2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5500392">"Type I and Type II Photosensitized Oxidation Reactions: Guidelines and Mechanistic Pathways"</a>. <i>Photochemistry and Photobiology</i>. <b>93</b> (4): <span class="nowrap">912–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fphp.12716">10.1111/php.12716</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5500392">5500392</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28084040">28084040</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Photochemistry+and+Photobiology&rft.atitle=Type+I+and+Type+II+Photosensitized+Oxidation+Reactions%3A+Guidelines+and+Mechanistic+Pathways&rft.volume=93&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E912-%3C%2Fspan%3E9&rft.date=2017&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5500392%23id-name%3DPMC&rft_id=info%3Apmid%2F28084040&rft_id=info%3Adoi%2F10.1111%2Fphp.12716&rft.aulast=Baptista&rft.aufirst=Maur%C3%ADcio+S.&rft.au=Cadet%2C+Jean&rft.au=Mascio%2C+Paolo+Di&rft.au=Ghogare%2C+Ashwini+A.&rft.au=Greer%2C+Alexander&rft.au=Hamblin%2C+Michael+R.&rft.au=Lorente%2C+Carolina&rft.au=Nunez%2C+Silvia+Cristina&rft.au=Ribeiro%2C+Martha+Sim%C3%B5es&rft.au=Thomas%2C+Andr%C3%A9s+H.&rft.au=Vignoni%2C+Mariana&rft.au=Yoshimura%2C+Tania+Mateus&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5500392&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOdaKawaseKurata1996" class="citation journal cs1">Oda, Masaji; Kawase, Takeshi; Kurata, Hiroyuki (1996). "1,3,5-Cyclooctatriene". <i>Organic Syntheses</i>. <b>73</b>: 240. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.073.0240">10.15227/orgsyn.073.0240</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=1%2C3%2C5-Cyclooctatriene&rft.volume=73&rft.pages=240&rft.date=1996&rft_id=info%3Adoi%2F10.15227%2Forgsyn.073.0240&rft.aulast=Oda&rft.aufirst=Masaji&rft.au=Kawase%2C+Takeshi&rft.au=Kurata%2C+Hiroyuki&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-JFH-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-JFH_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JFH_23-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHartwig2010" class="citation book cs1">Hartwig, John (2010). <i>Organotransition Metal Chemistry: From Bonding to Catalysis</i>. New York: University Science Books. p. 1160. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-938787-15-7" title="Special:BookSources/978-1-938787-15-7"><bdi>978-1-938787-15-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organotransition+Metal+Chemistry%3A+From+Bonding+to+Catalysis&rft.place=New+York&rft.pages=1160&rft.pub=University+Science+Books&rft.date=2010&rft.isbn=978-1-938787-15-7&rft.aulast=Hartwig&rft.aufirst=John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToreki2015" class="citation web cs1">Toreki, Rob (31 March 2015). <a rel="nofollow" class="external text" href="http://www.ilpi.com/organomet/alkene.html">"Alkene Complexes"</a>. <i>Organometallic HyperTextbook</i><span class="reference-accessdate">. Retrieved <span class="nowrap">29 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Organometallic+HyperTextbook&rft.atitle=Alkene+Complexes&rft.date=2015-03-31&rft.aulast=Toreki&rft.aufirst=Rob&rft_id=http%3A%2F%2Fwww.ilpi.com%2Forganomet%2Falkene.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-Wade2-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wade2_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWade2006" class="citation book cs1">Wade, L.G. (2006). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00wade_388"><i>Organic Chemistry</i></a></span> (6th ed.). Pearson <a href="/wiki/Prentice_Hall" title="Prentice Hall">Prentice Hall</a>. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00wade_388/page/n351">309</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4058-5345-3" title="Special:BookSources/978-1-4058-5345-3"><bdi>978-1-4058-5345-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=309&rft.edition=6th&rft.pub=Pearson+Prentice+Hall&rft.date=2006&rft.isbn=978-1-4058-5345-3&rft.aulast=Wade&rft.aufirst=L.G.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganicchemistry00wade_388&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-PataiBook1964-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-PataiBook1964_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSaunders1964" class="citation book cs1">Saunders, W. H. (1964). "Elimination Reactions in Solution". In Patai, Saul (ed.). <i>The Chemistry of Alkenes</i>. PATAI'S Chemistry of Functional Groups. Wiley Interscience. pp. <span class="nowrap">149–</span>201. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771044">10.1002/9780470771044</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77104-4" title="Special:BookSources/978-0-470-77104-4"><bdi>978-0-470-77104-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Elimination+Reactions+in+Solution&rft.btitle=The+Chemistry+of+Alkenes&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pages=%3Cspan+class%3D%22nowrap%22%3E149-%3C%2Fspan%3E201&rft.pub=Wiley+Interscience&rft.date=1964&rft_id=info%3Adoi%2F10.1002%2F9780470771044&rft.isbn=978-0-470-77104-4&rft.aulast=Saunders&rft.aufirst=W.+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-Cram1956-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cram1956_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCramGreeneDepuy1956" class="citation journal cs1">Cram, D.J.; Greene, Frederick D.; Depuy, C. H. (1956). "Studies in Stereochemistry. XXV. Eclipsing Effects in the E2 Reaction1". <i>Journal of the American Chemical Society</i>. <b>78</b> (4): <span class="nowrap">790–</span>6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01585a024">10.1021/ja01585a024</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Studies+in+Stereochemistry.+XXV.+Eclipsing+Effects+in+the+E2+Reaction1&rft.volume=78&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E790-%3C%2Fspan%3E6&rft.date=1956&rft_id=info%3Adoi%2F10.1021%2Fja01585a024&rft.aulast=Cram&rft.aufirst=D.J.&rft.au=Greene%2C+Frederick+D.&rft.au=Depuy%2C+C.+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-CopeElimination1973-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-CopeElimination1973_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBachAndrzejewskiDusold1973" class="citation journal cs1">Bach, R.D.; Andrzejewski, Denis; Dusold, Laurence R. (1973). "Mechanism of the Cope elimination". <i>J. Org. Chem</i>. <b>38</b> (9): <span class="nowrap">1742–</span>3. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00949a029">10.1021/jo00949a029</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Mechanism+of+the+Cope+elimination&rft.volume=38&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1742-%3C%2Fspan%3E3&rft.date=1973&rft_id=info%3Adoi%2F10.1021%2Fjo00949a029&rft.aulast=Bach&rft.aufirst=R.D.&rft.au=Andrzejewski%2C+Denis&rft.au=Dusold%2C+Laurence+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCrowell1964" class="citation book cs1">Crowell, Thomas I. (1964). "Alkene-Forming Condensation Reactions". In Patai, Saul (ed.). <i>The Chemistry of Alkenes</i>. PATAI'S Chemistry of Functional Groups. Wiley Interscience. pp. <span class="nowrap">241–</span>270. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771044.ch4">10.1002/9780470771044.ch4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77104-4" title="Special:BookSources/978-0-470-77104-4"><bdi>978-0-470-77104-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alkene-Forming+Condensation+Reactions&rft.btitle=The+Chemistry+of+Alkenes&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pages=%3Cspan+class%3D%22nowrap%22%3E241-%3C%2Fspan%3E270&rft.pub=Wiley+Interscience&rft.date=1964&rft_id=info%3Adoi%2F10.1002%2F9780470771044.ch4&rft.isbn=978-0-470-77104-4&rft.aulast=Crowell&rft.aufirst=Thomas+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-KO-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-KO_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDelaudeNoels2005" class="citation encyclopaedia cs1">Delaude, Lionel; Noels, Alfred F. (2005). "Metathesis". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. Weinheim: Wiley-VCH. pp. metanoel.a01. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.metanoel.a01">10.1002/0471238961.metanoel.a01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-23896-6" title="Special:BookSources/978-0-471-23896-6"><bdi>978-0-471-23896-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Metathesis&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.place=Weinheim&rft.pages=metanoel.a01&rft.pub=Wiley-VCH&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F0471238961.metanoel.a01&rft.isbn=978-0-471-23896-6&rft.aulast=Delaude&rft.aufirst=Lionel&rft.au=Noels%2C+Alfred+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-Vogt2010-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-Vogt2010_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVogt2010" class="citation journal cs1">Vogt, D. (2010). "Cobalt-Catalyzed Asymmetric Hydrovinylation". <i>Angew. Chem. Int. Ed</i>. <b>49</b> (40): <span class="nowrap">7166–</span>8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201003133">10.1002/anie.201003133</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20672269">20672269</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Cobalt-Catalyzed+Asymmetric+Hydrovinylation&rft.volume=49&rft.issue=40&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7166-%3C%2Fspan%3E8&rft.date=2010&rft_id=info%3Adoi%2F10.1002%2Fanie.201003133&rft_id=info%3Apmid%2F20672269&rft.aulast=Vogt&rft.aufirst=D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-ZweifelNantz-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-ZweifelNantz_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZweifelNantz2007" class="citation book cs1">Zweifel, George S.; Nantz, Michael H. (2007). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/modernorganicsyn00zwei"><i>Modern Organic Synthesis: An Introduction</i></a></span>. W. H. Freeman. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/modernorganicsyn00zwei/page/n373">366</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7167-7266-8" title="Special:BookSources/978-0-7167-7266-8"><bdi>978-0-7167-7266-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+Organic+Synthesis%3A+An+Introduction&rft.pages=366&rft.pub=W.+H.+Freeman&rft.date=2007&rft.isbn=978-0-7167-7266-8&rft.aulast=Zweifel&rft.aufirst=George+S.&rft.au=Nantz%2C+Michael+H.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fmodernorganicsyn00zwei&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-Ninkuu_2021-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ninkuu_2021_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNinkuuZhangYanFu2021" class="citation journal cs1">Ninkuu, Vincent; Zhang, Lin; Yan, Jianpei; et al. (June 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199371">"Biochemistry of Terpenes and Recent Advances in Plant Protection"</a>. <i>International Journal of Molecular Sciences</i>. <b>22</b> (11): 5710. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fijms22115710">10.3390/ijms22115710</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199371">8199371</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34071919">34071919</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Molecular+Sciences&rft.atitle=Biochemistry+of+Terpenes+and+Recent+Advances+in+Plant+Protection&rft.volume=22&rft.issue=11&rft.pages=5710&rft.date=2021-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8199371%23id-name%3DPMC&rft_id=info%3Apmid%2F34071919&rft_id=info%3Adoi%2F10.3390%2Fijms22115710&rft.aulast=Ninkuu&rft.aufirst=Vincent&rft.au=Zhang%2C+Lin&rft.au=Yan%2C+Jianpei&rft.au=Fu%2C+Zenchao&rft.au=Yang%2C+Tengfeng&rft.au=Zeng%2C+Hongmei&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8199371&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFreissinetGlavinArcherTeinturier2025" class="citation journal cs1">Freissinet, Caroline; Glavin, Daniel P.; Archer, P. Douglas; Teinturier, Samuel; Buch, Arnaud; Szopa, Cyril; Lewis, James M. T.; Williams, Amy J.; Navarro-Gonzalez, Rafael; Dworkin, Jason P.; Franz, Heather. B.; Millan, Maëva; Eigenbrode, Jennifer L.; Summons, R. E.; House, Christopher H. (March 2025). <a rel="nofollow" class="external text" href="https://www.pnas.org/doi/10.1073/pnas.2420580122">"Long-chain alkanes preserved in a Martian mudstone"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>122</b> (13): e2420580122. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.2420580122">10.1073/pnas.2420580122</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=Long-chain+alkanes+preserved+in+a+Martian+mudstone&rft.volume=122&rft.issue=13&rft.pages=e2420580122&rft.date=2025-03&rft_id=info%3Adoi%2F10.1073%2Fpnas.2420580122&rft.aulast=Freissinet&rft.aufirst=Caroline&rft.au=Glavin%2C+Daniel+P.&rft.au=Archer%2C+P.+Douglas&rft.au=Teinturier%2C+Samuel&rft.au=Buch%2C+Arnaud&rft.au=Szopa%2C+Cyril&rft.au=Lewis%2C+James+M.+T.&rft.au=Williams%2C+Amy+J.&rft.au=Navarro-Gonzalez%2C+Rafael&rft.au=Dworkin%2C+Jason+P.&rft.au=Franz%2C+Heather.+B.&rft.au=Millan%2C+Ma%C3%ABva&rft.au=Eigenbrode%2C+Jennifer+L.&rft.au=Summons%2C+R.+E.&rft.au=House%2C+Christopher+H.&rft_id=https%3A%2F%2Fwww.pnas.org%2Fdoi%2F10.1073%2Fpnas.2420580122&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> <li id="cite_note-murr2014-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-murr2014_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMcMurry2014" class="citation book cs1">McMurry, John E. (2014). <i>Organic Chemistry with Biological Applications</i> (3rd ed.). Cengage Learning. p. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KDIeCgAAQBAJ&pg=PA189">189</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-285-84291-2" title="Special:BookSources/978-1-285-84291-2"><bdi>978-1-285-84291-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry+with+Biological+Applications&rft.pages=189&rft.edition=3rd&rft.pub=Cengage+Learning&rft.date=2014&rft.isbn=978-1-285-84291-2&rft.aulast=McMurry&rft.aufirst=John+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkene" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Hydrocarbons181" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:azzurro;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrocarbons" title="Template:Hydrocarbons"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrocarbons" title="Template talk:Hydrocarbons"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons181" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2135" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a class="mw-selflink selflink">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /></div><div role="navigation" class="navbox" aria-labelledby="Alkenes39" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alkenes" title="Template:Alkenes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alkenes" title="Template talk:Alkenes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alkenes" title="Special:EditPage/Template:Alkenes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alkenes39" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Alkenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub></span>)</li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">6</sub></span>)</li> <li><a href="/wiki/Butene" title="Butene">Butene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">8</sub></span>)</li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">10</sub></span>)</li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub></span>)</li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">14</sub></span>)</li> <li><a href="/wiki/Octene" title="Octene">Octene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">16</sub></span>)</li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">18</sub></span>)</li> <li><a href="/wiki/Decene" title="Decene">Decene</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">20</sub></span>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a> from <a href="/wiki/Haloalkane" title="Haloalkane">haloalkane</a></li> <li><a href="/wiki/Dehydration_reaction" title="Dehydration reaction">Dehydration reaction</a> from <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a></li> <li><a href="/wiki/Semihydrogenation" class="mw-redirect" title="Semihydrogenation">Semihydrogenation</a> from <a href="/wiki/Alkyne" title="Alkyne">alkyne</a></li> <li><a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a></li> <li><a href="/wiki/Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a></li> <li><a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Grieco_elimination" title="Grieco elimination">Grieco elimination</a></li> <li><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrazone_iodination" title="Hydrazone iodination">Hydrazone iodination</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Halogenation" title="Halogenation">Halogenation</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a></li> <li><a href="/wiki/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a></li> <li><a href="/wiki/Oxymercuration_reaction" title="Oxymercuration reaction">Oxymercuration reaction</a></li> <li><a href="/wiki/Hydroboration" title="Hydroboration">Hydroboration</a></li> <li><a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></li> <li><a href="/wiki/Epoxidation" class="mw-redirect" title="Epoxidation">Epoxidation</a></li> <li><a href="/wiki/Dihydroxylation" title="Dihydroxylation">Dihydroxylation</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a></li> <li><a href="/wiki/Polymerization" title="Polymerization">Polymerization</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a></li> <li><a href="/wiki/Dehydrogenation" title="Dehydrogenation">Dehydrogenation</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Friedel-Crafts_Alkylation" class="mw-redirect" title="Friedel-Crafts Alkylation">Friedel-Crafts Alkylation</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups729" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a class="mw-selflink selflink">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li> <li><a href="/wiki/Thia-crown_ether" title="Thia-crown ether">Thia-crown ether</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry854" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Branches_of_chemistry" title="Template:Branches of chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Branches_of_chemistry" title="Template talk:Branches of chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Branches_of_chemistry" title="Special:EditPage/Template:Branches of chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Branches_of_chemistry854" style="font-size:114%;margin:0 4em">Branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Glossary_of_chemical_formulae" title="Glossary of chemical formulae">Glossary of chemical formulae</a></li> <li><a href="/wiki/List_of_biomolecules" title="List of biomolecules">List of biomolecules</a></li> <li><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">List of inorganic compounds</a></li> <li><a href="/wiki/Periodic_table" title="Periodic table">Periodic table</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Nanochemistry" title="Nanochemistry">Nanochemistry</a> <ul><li><a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">Supramolecular chemistry</a></li></ul></li> <li><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> <ul><li><a href="/wiki/Green_chemistry" title="Green chemistry">Green chemistry</a></li> <li><a href="/wiki/Click_chemistry" title="Click chemistry">Click chemistry</a></li> <li><a href="/wiki/Combinatorial_chemistry" title="Combinatorial chemistry">Combinatorial chemistry</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li></ul></li> <li><a href="/wiki/Chemical_engineering" title="Chemical engineering">Chemical engineering</a> <ul><li><a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometry</a></li></ul></li> <li><a href="/wiki/Materials_science" title="Materials science">Materials science</a> <ul><li><a href="/wiki/Metallurgy" title="Metallurgy">Metallurgy</a></li> <li><a href="/wiki/Ceramic_engineering" title="Ceramic engineering">Ceramic engineering</a></li> <li><a href="/wiki/Polymer_science" title="Polymer science">Polymer science</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/History_of_chemistry" title="History of chemistry">History of chemistry</a></li> <li><a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a></li> <li><a href="/wiki/Timeline_of_chemistry" title="Timeline of chemistry">Timeline of chemistry</a> <ul><li><a href="/wiki/Discovery_of_chemical_elements" title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chemistry" title="Category:Chemistry">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/20px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Chemistry" class="extiw" title="commons:Category:Chemistry">Commons</a></b></li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Symbol_portal_class.svg" class="mw-file-description" title="Portal"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/20px-Symbol_portal_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/40px-Symbol_portal_class.svg.png 1.5x" data-file-width="180" data-file-height="185" /></a></span> <b><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Portal</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="WikiProject"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/16px-People_icon.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/24px-People_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/32px-People_icon.svg.png 2x" data-file-width="100" data-file-height="100" /></span></span> <b><a href="/wiki/Wikipedia:WikiProject_Chemistry" title="Wikipedia:WikiProject Chemistry">WikiProject</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319" /></div><div role="navigation" class="navbox authority-control" aria-labelledby="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q81406#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1516" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q81406#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1516" style="font-size:114%;margin:0 4em"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q81406#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="http://id.worldcat.org/fast/805415/">FAST</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4001207-4">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85094589">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Alcènes"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11948674t">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Alcènes"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11948674t">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00562061">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="alkeny"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph462040&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007546028505171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Alkene&oldid=1282619601">https://en.wikipedia.org/w/index.php?title=Alkene&oldid=1282619601</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Category</a>: <ul><li><a href="/wiki/Category:Alkenes" title="Category:Alkenes">Alkenes</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_August_2022" title="Category:Use dmy dates from August 2022">Use dmy dates from August 2022</a></li><li><a href="/wiki/Category:Wikipedia_articles_needing_clarification_from_September_2023" title="Category:Wikipedia articles needing clarification from September 2023">Wikipedia articles needing clarification from September 2023</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 27 March 2025, at 15:14<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Alkene&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://www.wikimedia.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/static/images/footer/wikimedia-button.svg" width="84" height="29"><img src="/static/images/footer/wikimedia.svg" width="25" height="25" alt="Wikimedia Foundation" lang="en" loading="lazy"></picture></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/w/resources/assets/poweredby_mediawiki.svg" width="88" height="31"><img src="/w/resources/assets/mediawiki_compact.svg" alt="Powered by MediaWiki" lang="en" width="25" height="25" loading="lazy"></picture></a></li> </ul> </footer> </div> </div> </div> <div class="vector-header-container vector-sticky-header-container"> <div id="vector-sticky-header" class="vector-sticky-header"> <div class="vector-sticky-header-start"> <div class="vector-sticky-header-icon-start vector-button-flush-left vector-button-flush-right" aria-hidden="true"> <button class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-sticky-header-search-toggle" tabindex="-1" data-event-name="ui.vector-sticky-search-form.icon"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </button> </div> <div role="search" class="vector-search-box-vue vector-search-box-show-thumbnail vector-search-box"> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail"> <form action="/w/index.php" id="vector-sticky-search-form" class="cdx-search-input cdx-search-input--has-end-button"> <div class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia"> <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <div class="vector-sticky-header-context-bar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-sticky-header-toc" class="vector-dropdown mw-portlet mw-portlet-sticky-header-toc vector-sticky-header-toc vector-button-flush-left" > <input type="checkbox" id="vector-sticky-header-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-sticky-header-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-sticky-header-toc-label" for="vector-sticky-header-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-sticky-header-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div class="vector-sticky-header-context-bar-primary" aria-hidden="true" ><span class="mw-page-title-main">Alkene</span></div> </div> </div> <div class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>83 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-5c6f46dcf-q4v2d","wgBackendResponseTime":238,"wgPageParseReport":{"limitreport":{"cputime":"0.790","walltime":"1.033","ppvisitednodes":{"value":7133,"limit":1000000},"postexpandincludesize":{"value":277568,"limit":2097152},"templateargumentsize":{"value":7082,"limit":2097152},"expansiondepth":{"value":15,"limit":100},"expensivefunctioncount":{"value":11,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":193997,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 728.320 1 -total"," 39.15% 285.166 1 Template:Reflist"," 23.21% 169.026 16 Template:Navbox"," 14.09% 102.637 10 Template:Cite_book"," 13.89% 101.177 1 Template:Hydrocarbons"," 8.43% 61.401 31 Template:Chem2"," 8.43% 61.383 11 Template:Cite_journal"," 7.43% 54.148 1 Template:Short_description"," 5.23% 38.098 1 Template:Authority_control"," 4.88% 35.515 9 Template:Cite_web"]},"scribunto":{"limitreport-timeusage":{"value":"0.408","limit":"10.000"},"limitreport-memusage":{"value":8527669,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-5c6f46dcf-6mmvb","timestamp":"20250331025547","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Alkene","url":"https:\/\/en.wikipedia.org\/wiki\/Alkene","sameAs":"http:\/\/www.wikidata.org\/entity\/Q81406","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q81406","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2001-12-01T09:30:27Z","dateModified":"2025-03-27T15:14:21Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/c\/c3\/Ethylene-3D-vdW.png","headline":"unsaturated chemical compound containing one carbon-to-carbon double bond"}</script> </body> </html>