CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-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-disabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Ether: Difference between revisions - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-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-disabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day 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":"a4a33c07-d892-4b9c-aaea-377a885db091","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Ether","wgTitle":"Ether","wgCurRevisionId":1259858737,"wgRevisionId":1259858737,"wgArticleId":9263,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description is different from Wikidata","Ethers","Functional groups","Impression material"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Ether","wgRelevantArticleId":9263,"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":20000,"extRevisionSliderTimeOffset":0,"wgDiffOldId":1259809383,"wgDiffNewId":1259858737,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q103230","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":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.visualEditor.diffPage.init.styles":"ready","oojs-ui.styles.icons-accessibility":"ready","oojs-ui.styles.icons-editing-advanced":"ready","oojs-ui-core.styles":"ready","oojs-ui.styles.indicators":"ready","mediawiki.widgets.styles":"ready","oojs-ui-core.icons":"ready","ext.RevisionSlider.lazyCss":"ready","mediawiki.interface.helpers.styles":"ready","mediawiki.diff.styles":"ready","ext.cite.styles":"ready","mediawiki.helplink":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"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.visualEditor.diffPage.init","ext.RevisionSlider.lazyJs","mediawiki.diff","ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","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","wikibase.sidebar.tracking"];</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.RevisionSlider.lazyCss%7Cext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.visualEditor.diffPage.init.styles%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cmediawiki.diff.styles%7Cmediawiki.helplink%7Cmediawiki.interface.helpers.styles%7Cmediawiki.widgets.styles%7Coojs-ui-core.icons%2Cstyles%7Coojs-ui.styles.icons-accessibility%2Cicons-editing-advanced%2Cindicators%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.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="noindex,nofollow,max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/1200px-Ether-%28general%29.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="555"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/800px-Ether-%28general%29.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="370"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/640px-Ether-%28general%29.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="296"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Ether: Difference between revisions - 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/Ether"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Ether&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/Ether"> <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="//login.wikimedia.org"> </head> <body class="mw-article-diff skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Ether rootpage-Ether 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" > <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> </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/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_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=Ether&returntoquery=curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383" 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=Ether&returntoquery=curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383" 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/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_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=Ether&returntoquery=curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383" 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=Ether&returntoquery=curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383" 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-Structure_and_bonding" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</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-Vinyl-_and_acetylenic_ethers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vinyl-_and_acetylenic_ethers"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Vinyl- and acetylenic ethers</span> </div> </a> <ul id="toc-Vinyl-_and_acetylenic_ethers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-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 Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Trivial_name" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Trivial_name"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Trivial name</span> </div> </a> <ul id="toc-Trivial_name-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polyethers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polyethers"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Polyethers</span> </div> </a> <ul id="toc-Polyethers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Related_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Related_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Related compounds</span> </div> </a> <ul id="toc-Related_compounds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <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> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <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-Cleavage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cleavage"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Cleavage</span> </div> </a> <ul id="toc-Cleavage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Peroxide_formation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Peroxide_formation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Peroxide formation</span> </div> </a> <ul id="toc-Peroxide_formation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lewis_bases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lewis_bases"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Lewis bases</span> </div> </a> <ul id="toc-Lewis_bases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alpha-halogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alpha-halogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Alpha-halogenation</span> </div> </a> <ul id="toc-Alpha-halogenation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <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-Dehydration_of_alcohols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydration_of_alcohols"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Dehydration of alcohols</span> </div> </a> <ul id="toc-Dehydration_of_alcohols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrophilic_addition_of_alcohols_to_alkenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrophilic_addition_of_alcohols_to_alkenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Electrophilic addition of alcohols to alkenes</span> </div> </a> <ul id="toc-Electrophilic_addition_of_alcohols_to_alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epoxides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epoxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Epoxides</span> </div> </a> <ul id="toc-Epoxides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Williamson_and_Ullmann_ether_syntheses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Williamson_and_Ullmann_ether_syntheses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Williamson and Ullmann ether syntheses</span> </div> </a> <ul id="toc-Williamson_and_Ullmann_ether_syntheses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Important_ethers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Important_ethers"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Important ethers</span> </div> </a> <ul id="toc-Important_ethers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</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" > <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">Ether: Difference between revisions</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 76 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-76" 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">76 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/Eter_(chemie)" title="Eter (chemie) – Afrikaans" lang="af" hreflang="af" data-title="Eter (chemie)" 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%A5%D9%8A%D8%AB%D8%B1" title="إيثر – Arabic" lang="ar" hreflang="ar" data-title="إيثر" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sad%C9%99_efirl%C9%99r" title="Sadə efirlər – Azerbaijani" lang="az" hreflang="az" data-title="Sadə efirlər" 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%87%E0%A6%A5%E0%A6%BE%E0%A6%B0" title="ইথার – Bangla" lang="bn" hreflang="bn" data-title="ইথার" 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%9F%D1%80%D0%BE%D1%81%D1%82%D1%8B%D1%8F_%D1%8D%D1%84%D1%96%D1%80%D1%8B" title="Простыя эфіры – Belarusian" lang="be" hreflang="be" data-title="Простыя эфіры" 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%9F%D1%80%D0%BE%D1%81%D1%82%D1%8B%D1%8F_%D1%8D%D1%82%D1%8D%D1%80%D1%8B" title="Простыя этэры – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Простыя этэры" 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/Eter" title="Eter – Central Bikol" lang="bcl" hreflang="bcl" data-title="Eter" 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%95%D1%82%D0%B5%D1%80_(%D1%85%D0%B8%D0%BC%D0%B8%D1%8F)" title="Етер (химия) – Bulgarian" lang="bg" hreflang="bg" data-title="Етер (химия)" 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/Eter" title="Eter – Bosnian" lang="bs" hreflang="bs" data-title="Eter" 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/%C3%88ter" title="Èter – Catalan" lang="ca" hreflang="ca" data-title="Èter" 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/Ethery" title="Ethery – Czech" lang="cs" hreflang="cs" data-title="Ethery" 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/Ether" title="Ether – Welsh" lang="cy" hreflang="cy" data-title="Ether" 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/Ether_(kemi)" title="Ether (kemi) – Danish" lang="da" hreflang="da" data-title="Ether (kemi)" 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/Ether" title="Ether – German" lang="de" hreflang="de" data-title="Ether" 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/Eetrid" title="Eetrid – Estonian" lang="et" hreflang="et" data-title="Eetrid" 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%B9%CE%B8%CE%AD%CF%81%CE%B5%CF%82" title="Αιθέρες – Greek" lang="el" hreflang="el" data-title="Αιθέρες" 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/%C3%89ter_(qu%C3%ADmica)" title="Éter (química) – Spanish" lang="es" hreflang="es" data-title="Éter (química)" 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/Etero_(kemio)" title="Etero (kemio) – Esperanto" lang="eo" hreflang="eo" data-title="Etero (kemio)" 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/Eterrak" title="Eterrak – Basque" lang="eu" hreflang="eu" data-title="Eterrak" 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%A7%D8%AA%D8%B1" title="اتر – Persian" lang="fa" hreflang="fa" data-title="اتر" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89ther-oxyde" title="Éther-oxyde – French" lang="fr" hreflang="fr" data-title="Éther-oxyde" 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/%C3%89itear" title="Éitear – Irish" lang="ga" hreflang="ga" data-title="Éitear" 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/%C3%89ter" title="Éter – Galician" lang="gl" hreflang="gl" data-title="Éter" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%88%E0%AA%A5%E0%AA%B0" title="ઈથર – Gujarati" lang="gu" hreflang="gu" data-title="ઈથર" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%84%B0" title="에터 – Korean" lang="ko" hreflang="ko" data-title="에터" 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%B5%D5%A9%D5%A5%D6%80%D5%B6%D5%A5%D6%80" title="Եթերներ – Armenian" lang="hy" hreflang="hy" data-title="Եթերներ" 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%88%E0%A4%A5%E0%A4%B0" title="ईथर – Hindi" lang="hi" hreflang="hi" data-title="ईथर" 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/Eteri" title="Eteri – Croatian" lang="hr" hreflang="hr" data-title="Eteri" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Eter" title="Eter – Indonesian" lang="id" hreflang="id" data-title="Eter" 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-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Ethere" title="Ethere – Interlingua" lang="ia" hreflang="ia" data-title="Ethere" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Eteri" title="Eteri – Italian" lang="it" hreflang="it" data-title="Eteri" 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%AA%D7%A8_(%D7%9B%D7%99%D7%9E%D7%99%D7%94)" title="אתר (כימיה) – Hebrew" lang="he" hreflang="he" data-title="אתר (כימיה)" 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%88%E0%B2%A5%E0%B2%B0%E0%B3%8D%E2%80%8D%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಈಥರ್‍ಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಈಥರ್‍ಗಳು" 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%94%E1%83%97%E1%83%94%E1%83%A0%E1%83%98" title="ეთერი – Georgian" lang="ka" hreflang="ka" data-title="ეთერი" 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%96%D0%B0%D0%B9_%D1%8D%D1%84%D0%B8%D1%80%D0%BB%D0%B5%D1%80" title="Жай эфирлер – Kazakh" lang="kk" hreflang="kk" data-title="Жай эфирлер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Aether_(chemica)" title="Aether (chemica) – Latin" lang="la" hreflang="la" data-title="Aether (chemica)" 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/%C4%92teri" title="Ēteri – Latvian" lang="lv" hreflang="lv" data-title="Ēteri" 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/Eteriai" title="Eteriai – Lithuanian" lang="lt" hreflang="lt" data-title="Eteriai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/%C3%89ter_(k%C3%A9mia)" title="Éter (kémia) – Hungarian" lang="hu" hreflang="hu" data-title="Éter (kémia)" 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%95%D1%82%D0%B5%D1%80" title="Етер – Macedonian" lang="mk" hreflang="mk" data-title="Етер" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Eter" title="Eter – Malay" lang="ms" hreflang="ms" data-title="Eter" 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-fj mw-list-item"><a href="https://fj.wikipedia.org/wiki/Ether" title="Ether – Fijian" lang="fj" hreflang="fj" data-title="Ether" 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/Ether_(scheikunde)" title="Ether (scheikunde) – Dutch" lang="nl" hreflang="nl" data-title="Ether (scheikunde)" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A4%B0_(%E0%A4%B0%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8)" title="इथर (रसायन) – Nepali" lang="ne" hreflang="ne" data-title="इथर (रसायन)" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%BC%E3%83%86%E3%83%AB_(%E5%8C%96%E5%AD%A6)" title="エーテル (化学) – Japanese" lang="ja" hreflang="ja" data-title="エーテル (化学)" 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/Eter_(kjemi)" title="Eter (kjemi) – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Eter (kjemi)" 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/Eterar" title="Eterar – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Eterar" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Et%C3%A8r_(quimia)" title="Etèr (quimia) – Occitan" lang="oc" hreflang="oc" data-title="Etèr (quimia)" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Efirlar" title="Efirlar – Uzbek" lang="uz" hreflang="uz" data-title="Efirlar" 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%88%E0%A8%A5%E0%A8%B0" title="ਈਥਰ – Punjabi" lang="pa" hreflang="pa" data-title="ਈਥਰ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%AA%DA%BE%D8%B1" title="ایتھر – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ایتھر" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%8A%D8%AA%D8%B1" title="ايتر – Pashto" lang="ps" hreflang="ps" data-title="ايتر" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Ether" title="Ether – Low German" lang="nds" hreflang="nds" data-title="Ether" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Etery" title="Etery – Polish" lang="pl" hreflang="pl" data-title="Etery" 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/%C3%89ter" title="Éter – Portuguese" lang="pt" hreflang="pt" data-title="Éter" 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/Eter" title="Eter – Romanian" lang="ro" hreflang="ro" data-title="Eter" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D1%81%D1%82%D1%8B%D0%B5_%D1%8D%D1%84%D0%B8%D1%80%D1%8B" title="Простые эфиры – Russian" lang="ru" hreflang="ru" data-title="Простые эфиры" 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/Eteri" title="Eteri – Albanian" lang="sq" hreflang="sq" data-title="Eteri" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/%C3%89ter_(ch%C3%A9mia)" title="Éter (chémia) – Slovak" lang="sk" hreflang="sk" data-title="Éter (chémia)" 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/Eter" title="Eter – Slovenian" lang="sl" hreflang="sl" data-title="Eter" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D1%80_(%D1%85%D0%B5%D0%BC%D0%B8%D1%98%D0%B0)" title="Етар (хемија) – Serbian" lang="sr" hreflang="sr" data-title="Етар (хемија)" 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/Etar_(hemija)" title="Etar (hemija) – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etar (hemija)" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Eetterit" title="Eetterit – Finnish" lang="fi" hreflang="fi" data-title="Eetterit" 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/Etrar" title="Etrar – Swedish" lang="sv" hreflang="sv" data-title="Etrar" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%88%E0%AE%A4%E0%AE%B0%E0%AF%8D" title="ஈதர் – Tamil" lang="ta" hreflang="ta" data-title="ஈதர்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%88%E0%B0%A5%E0%B0%B0%E0%B1%81" title="ఈథరు – Telugu" lang="te" hreflang="te" data-title="ఈథరు" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AD%E0%B8%B5%E0%B9%80%E0%B8%97%E0%B8%AD%E0%B8%A3%E0%B9%8C" title="อีเทอร์ – Thai" lang="th" hreflang="th" data-title="อีเทอร์" 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/Eter" title="Eter – Turkish" lang="tr" hreflang="tr" data-title="Eter" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-tyv mw-list-item"><a href="https://tyv.wikipedia.org/wiki/%D0%91%D3%A9%D0%B4%D2%AF%D2%AF%D0%BD_%D1%8D%D1%84%D0%B8%D1%80%D0%BB%D0%B5%D1%80" title="Бөдүүн эфирлер – Tuvinian" lang="tyv" hreflang="tyv" data-title="Бөдүүн эфирлер" data-language-autonym="Тыва дыл" data-language-local-name="Tuvinian" class="interlanguage-link-target"><span>Тыва дыл</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%B5%D1%80%D0%B8" title="Етери – Ukrainian" lang="uk" hreflang="uk" data-title="Етери" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ether" title="Ether – Vietnamese" lang="vi" hreflang="vi" data-title="Ether" 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/%E9%86%9A" title="醚 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="醚" 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/Eter" title="Eter – Waray" lang="war" hreflang="war" data-title="Eter" 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/%E9%86%9A" title="醚 – Wu" lang="wuu" hreflang="wuu" data-title="醚" 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/%E9%86%9A" title="醚 – Cantonese" lang="yue" hreflang="yue" data-title="醚" 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/%E9%86%9A" title="醚 – Chinese" lang="zh" hreflang="zh" data-title="醚" 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/Q103230#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/Ether" 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:Ether" 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/Ether"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Ether&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=Ether&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/Ether"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Ether&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=Ether&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/Ether" 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/Ether" 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="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Ether&oldid=1259858737" 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=Ether&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=Ether&id=1259858737&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%2Fw%2Findex.php%3Ftitle%3DEther%26curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383"><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%2Fw%2Findex.php%3Ftitle%3DEther%26curid%3D9263%26diff%3D1259858737%26oldid%3D1259809383"><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=Ether&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=Ether&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:Ethers" 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/Ethers" 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/Ether" 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/Q103230" 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 id="mw-indicator-mw-helplink" class="mw-indicator"><a href="https://www.mediawiki.org/wiki/Special:MyLanguage/Help:Diff" target="_blank" class="mw-helplink"><span class="mw-helplink-icon"></span>Help</a></div> </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-revslider-container"><span style='width: 100%; text-align: center;' id='ooui-php-1' class='mw-revslider-toggle-button oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-indicatorElement oo-ui-labelElement oo-ui-buttonWidget' data-ooui='{"_":"OO.ui.ButtonWidget","rel":["nofollow"],"framed":false,"indicator":"down","label":"Browse history interactively","title":"Open revision slider","classes":["mw-revslider-toggle-button"]}'><a role='button' title='Open revision slider' tabindex='0' rel='nofollow' class='oo-ui-buttonElement-button'><span class='oo-ui-iconElement-icon oo-ui-iconElement-noIcon'></span><span class='oo-ui-labelElement-label'>Browse history interactively</span><span class='oo-ui-indicatorElement-indicator oo-ui-indicator-down'></span></a></span><div class="mw-revslider-slider-wrapper" style="display: none;"><div class="mw-revslider-placeholder"><div class="mw-revslider-spinner"><div class="mw-revslider-bounce"></div></div></div></div></div><div class="mw-diff-revision-history-links"><a href="/w/index.php?title=Ether&diff=prev&oldid=1259809383" class="mw-diff-revision-history-link-previous" title="Ether">← Previous edit</a></div><div class="mw-diff-table-prefix" dir="ltr" lang="en"><div class="mw-diff-inline-legend oo-ui-element-hidden"><span class="mw-diff-inline-legend-del">Content deleted</span> <span class="mw-diff-inline-legend-ins">Content added</span></div><div class="ve-init-mw-diffPage-diffMode"><span class='oo-ui-widget oo-ui-widget-enabled oo-ui-buttonGroupWidget'><span aria-disabled='true' class='oo-ui-widget oo-ui-widget-disabled oo-ui-buttonElement oo-ui-buttonElement-framed oo-ui-iconElement oo-ui-labelElement oo-ui-buttonWidget'><a role='button' tabindex='-1' aria-disabled='true' rel='nofollow' class='oo-ui-buttonElement-button'><span class='oo-ui-iconElement-icon oo-ui-icon-eye oo-ui-image-invert'></span><span class='oo-ui-labelElement-label'>Visual</span><span class='oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator oo-ui-image-invert'></span></a></span><span class='oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-framed oo-ui-iconElement oo-ui-labelElement oo-ui-buttonWidget oo-ui-buttonElement-active'><a role='button' tabindex='0' rel='nofollow' class='oo-ui-buttonElement-button'><span class='oo-ui-iconElement-icon oo-ui-icon-wikiText oo-ui-image-invert'></span><span class='oo-ui-labelElement-label'>Wikitext</span><span class='oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator oo-ui-image-invert'></span></a></span></span></div><div class="mw-diffPage-inlineToggle-container"><div id='mw-diffPage-inline-toggle-switch-layout' class='oo-ui-layout oo-ui-labelElement oo-ui-fieldLayout oo-ui-fieldLayout-align-left' data-ooui='{"_":"OO.ui.FieldLayout","fieldWidget":{"tag":"mw-diffPage-inline-toggle-switch"},"$overlay":true,"label":"Inline","title":"Switches between inline format and two-column format"}'><div class='oo-ui-fieldLayout-body'><span class='oo-ui-fieldLayout-header'><label title='Switches between inline format and two-column format' id='ooui-php-2' class='oo-ui-labelElement-label'>Inline</label></span><div class='oo-ui-fieldLayout-field'><div id='mw-diffPage-inline-toggle-switch' title='Switches between inline format and two-column format' aria-checked='false' tabindex='0' role='switch' aria-labelledby='ooui-php-2' class='oo-ui-widget oo-ui-widget-enabled oo-ui-toggleWidget oo-ui-toggleWidget-off oo-ui-toggleSwitchWidget' data-ooui='{"_":"OO.ui.ToggleSwitchWidget","href":"\/w\/index.php?title=Ether&curid=9263&diff=1259858737&oldid=1259809383&diff-type=inline","value":false,"title":"Switches between inline format and two-column format"}'><span class='oo-ui-toggleSwitchWidget-glow'></span><a href='/w/index.php?title=Ether&curid=9263&diff=1259858737&oldid=1259809383&diff-type=inline'><span class='oo-ui-toggleSwitchWidget-grip'></span></a></div></div></div></div></div></div><table class="diff diff-type-table diff-contentalign-left diff-editfont-monospace" data-mw="interface"> <col class="diff-marker" /> <col class="diff-content" /> <col class="diff-marker" /> <col class="diff-content" /> <tr class="diff-title" lang="en"> <td colspan="2" class="diff-otitle diff-side-deleted"><div id="mw-diff-otitle1"><strong><a href="/w/index.php?title=Ether&oldid=1259809383" title="Ether">Revision as of 04:37, 27 November 2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=Ether&action=edit&oldid=1259809383" title="Ether">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-11-27T04:37:40Z"></span></strong></div><div id="mw-diff-otitle2"><a href="/wiki/Special:Contributions/2601:742:8000:59B0:8069:B7F6:82AC:9491" class="mw-userlink mw-anonuserlink" title="Special:Contributions/2601:742:8000:59B0:8069:B7F6:82AC:9491" data-mw-revid="1259809383"><bdi>2601:742:8000:59b0:8069:b7f6:82ac:9491</bdi></a> <span class="mw-usertoollinks">(<a href="/w/index.php?title=User_talk:2601:742:8000:59B0:8069:B7F6:82AC:9491&action=edit&redlink=1" class="new mw-usertoollinks-talk" title="User talk:2601:742:8000:59B0:8069:B7F6:82AC:9491 (page does not exist)">talk</a>)</span><div class="mw-diff-usermetadata"></div></div><div id="mw-diff-otitle3"><span class="comment mw-comment-none">No edit summary</span></div><div id="mw-diff-otitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tags</a>: <span class="mw-tag-marker mw-tag-marker-mw-reverted">Reverted</span> <span class="mw-tag-marker mw-tag-marker-mobile_edit">Mobile edit</span> <span class="mw-tag-marker mw-tag-marker-mobile_web_edit">Mobile web edit</span></span></div><div id="mw-diff-otitle4"><a href="/w/index.php?title=Ether&diff=prev&oldid=1259809383" title="Ether" id="differences-prevlink">← Previous edit</a></div></td> <td colspan="2" class="diff-ntitle diff-side-added"><div id="mw-diff-ntitle1"><strong><a href="/w/index.php?title=Ether&oldid=1259858737" title="Ether">Latest revision as of 13:26, 27 November 2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=Ether&action=edit" title="Ether">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-11-27T13:26:45Z"></span> <span class="mw-diff-undo"><a href="/w/index.php?title=Ether&action=edit&undoafter=1259809383&undo=1259858737" title=""Undo" reverts this edit and opens the edit form in preview mode. It allows adding a reason in the summary.">undo</a></span></strong></div><div id="mw-diff-ntitle2"><a href="/wiki/User:Marbletan" class="mw-userlink" title="User:Marbletan" data-mw-revid="1259858737"><bdi>Marbletan</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Marbletan" class="mw-usertoollinks-talk" title="User talk:Marbletan">talk</a> | <a href="/wiki/Special:Contributions/Marbletan" class="mw-usertoollinks-contribs" title="Special:Contributions/Marbletan">contribs</a>)</span><div class="mw-diff-usermetadata"><div class="mw-diff-userroles"><a href="/wiki/Wikipedia:Extended_confirmed_editors" class="mw-redirect" title="Wikipedia:Extended confirmed editors">Extended confirmed users</a></div><div class="mw-diff-usereditcount"><span>4,643</span> edits</div></div></div><div id="mw-diff-ntitle3"> <span class="comment comment--without-parentheses">Undid revision <a href="/wiki/Special:Diff/1259809383" title="Special:Diff/1259809383">1259809383</a> by <a href="/wiki/Special:Contributions/2601:742:8000:59B0:8069:B7F6:82AC:9491" title="Special:Contributions/2601:742:8000:59B0:8069:B7F6:82AC:9491">2601:742:8000:59B0:8069:B7F6:82AC:9491</a> (<a href="/w/index.php?title=User_talk:2601:742:8000:59B0:8069:B7F6:82AC:9491&action=edit&redlink=1" class="new" title="User talk:2601:742:8000:59B0:8069:B7F6:82AC:9491 (page does not exist)">talk</a>)</span></div><div id="mw-diff-ntitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tag</a>: <span class="mw-tag-marker mw-tag-marker-mw-undo"><a href="/wiki/Wikipedia:Undo" class="mw-redirect" title="Wikipedia:Undo">Undo</a></span></span></div><div id="mw-diff-ntitle4"> </div></td> </tr><tr> <td colspan="2" class="diff-lineno">Line 3:</td> <td colspan="2" class="diff-lineno">Line 3:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>[[File:Ether-(general).svg|thumb|150px|The general structure of an ether. R and R' represent most [[organyl]] [[substituent]]s.]]</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>[[File:Ether-(general).svg|thumb|150px|The general structure of an ether. R and R' represent most [[organyl]] [[substituent]]s.]]</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>In [[organic chemistry]], '''ethers''' are a class of [[organic compound|compound]]s that contain an ether [[functional group|group]]—an [[oxygen]] atom bonded to two [[organyl]] groups (e.g., [[alkyl]] or [[aryl]]). They have the general formula {{chem2|R\sO\sR′}}, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or <del class="diffchange diffchange-inline">mixmatched</del> ethers.<ref>{{GoldBookRef|title=ethers|file=E02221}}</ref> A typical example of the first group is the [[solvent]] and [[anaesthetic]] [[diethyl ether]], commonly referred to simply as "ether" ({{chem2|CH3\sCH2\sO\sCH2\sCH3}}). Ethers are common in organic chemistry and even more prevalent in [[biochemistry]], as they are common linkages in [[carbohydrate]]s and [[lignin]].<ref>{{cite book|title=The Ether Linkage|year=1967|editor=Saul Patai|isbn= 978-0-470-77107-5|doi=10.1002/9780470771075|publisher=John Wiley & Sons|series=PATAI'S Chemistry of Functional Groups}}</ref></div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>In [[organic chemistry]], '''ethers''' are a class of [[organic compound|compound]]s that contain an ether [[functional group|group]]—an [[oxygen]] atom bonded to two [[organyl]] groups (e.g., [[alkyl]] or [[aryl]]). They have the general formula {{chem2|R\sO\sR′}}, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or <ins class="diffchange diffchange-inline">unsymmetrical</ins> ethers.<ref>{{GoldBookRef|title=ethers|file=E02221}}</ref> A typical example of the first group is the [[solvent]] and [[anaesthetic]] [[diethyl ether]], commonly referred to simply as "ether" ({{chem2|CH3\sCH2\sO\sCH2\sCH3}}). Ethers are common in organic chemistry and even more prevalent in [[biochemistry]], as they are common linkages in [[carbohydrate]]s and [[lignin]].<ref>{{cite book|title=The Ether Linkage|year=1967|editor=Saul Patai|isbn= 978-0-470-77107-5|doi=10.1002/9780470771075|publisher=John Wiley & Sons|series=PATAI'S Chemistry of Functional Groups}}</ref></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>==Structure and bonding==</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>==Structure and bonding==</div></td> </tr>  </table><hr class='diff-hr' id='mw-oldid' /> <h2 class='diff-currentversion-title'>Latest revision as of 13:26, 27 November 2024</h2> <div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')</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">For the substance whose common name is ether, see <a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a>. For the digital asset, see <a href="/wiki/Ethereum" title="Ethereum">Ethereum</a>. For other uses, see <a href="/wiki/Aether_(disambiguation)" class="mw-redirect mw-disambig" title="Aether (disambiguation)">Aether (disambiguation)</a>.</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ether-(general).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/150px-Ether-%28general%29.svg.png" decoding="async" width="150" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/225px-Ether-%28general%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Ether-%28general%29.svg/300px-Ether-%28general%29.svg.png 2x" data-file-width="512" data-file-height="237" /></a><figcaption>The general structure of an ether. R and R' represent most <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> <a href="/wiki/Substituent" title="Substituent">substituents</a>.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>ethers</b> are a class of <a href="/wiki/Organic_compound" title="Organic compound">compounds</a> that contain an ether <a href="/wiki/Functional_group" title="Functional group">group</a>—an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom bonded to two <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> groups (e.g., <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>). They have 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">R−O−R′</span>, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> A typical example of the first group is the <a href="/wiki/Solvent" title="Solvent">solvent</a> and <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a> <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, commonly referred to simply as "ether" (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−CH<sub class="template-chem2-sub">2</sub>−O−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span>). Ethers are common in organic chemistry and even more prevalent in <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, as they are common linkages in <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and <a href="/wiki/Lignin" title="Lignin">lignin</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <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=Ether&action=edit&section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethers feature bent <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−O−C</span> linkages. In <a href="/wiki/Dimethyl_ether" title="Dimethyl ether">dimethyl ether</a>, the <a href="/wiki/Molecular_geometry#Bonding" title="Molecular geometry">bond angle</a> is 111° and C–O distances are 141 <a href="/wiki/Picometre" title="Picometre">pm</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of <a href="/wiki/Valence_bond_theory" title="Valence bond theory">valence bond theory</a>, the hybridization at oxygen is sp<sup>3</sup>. </p><p>Oxygen is more <a href="/wiki/Electronegativity" title="Electronegativity">electronegative</a> than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">ketones</a> or <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a>), however. </p><p>Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR'. Examples of the former are <a href="/wiki/Dimethyl_ether" title="Dimethyl ether">dimethyl ether</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Dipropyl_ether" class="mw-redirect" title="Dipropyl ether">dipropyl ether</a> etc. Illustrative unsymmetrical ethers are <a href="/wiki/Anisole" title="Anisole">anisole</a> (methoxybenzene) and <a href="/wiki/Dimethoxyethane" title="Dimethoxyethane">dimethoxyethane</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Vinyl-_and_acetylenic_ethers">Vinyl- and acetylenic ethers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=2" title="Edit section: Vinyl- and acetylenic ethers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vinyl- and acetylenic ethers are far less common than alkyl or aryl ethers. Vinylethers, often called <a href="/wiki/Enol_ether" title="Enol ether">enol ethers</a>, are important intermediates in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. Acetylenic ethers are especially rare. <a href="/wiki/Di-tert-butoxyacetylene" title="Di-tert-butoxyacetylene">Di-tert-butoxyacetylene</a> is the most common example of this rare class of compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=3" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/IUPAC_Nomenclature" class="mw-redirect" title="IUPAC Nomenclature">IUPAC Nomenclature</a> system, ethers are named using the general formula <i>"alkoxyalkane"</i>, for example CH<sub>3</sub>–CH<sub>2</sub>–O–CH<sub>3</sub> is <a href="/wiki/Methoxyethane" title="Methoxyethane">methoxyethane</a>. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH<sub>3</sub> would be considered a <i>"<a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">methoxy</a>-"</i> group. The simpler <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> radical is written in front, so CH<sub>3</sub>–O–CH<sub>2</sub>CH<sub>3</sub> would be given as <i>methoxy</i>(CH<sub>3</sub>O)<i>ethane</i>(CH<sub>2</sub>CH<sub>3</sub>). </p> <div class="mw-heading mw-heading3"><h3 id="Trivial_name">Trivial name</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=4" title="Edit section: Trivial name"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>IUPAC rules are often not followed for simple ethers. The trivial names for simple ethers (i.e., those with none or few other functional groups) are a composite of the two substituents followed by "ether". For example, ethyl methyl ether (CH<sub>3</sub>OC<sub>2</sub>H<sub>5</sub>), diphenylether (C<sub>6</sub>H<sub>5</sub>OC<sub>6</sub>H<sub>5</sub>). As for other organic compounds, very common ethers acquired names before rules for nomenclature were formalized. Diethyl ether is simply called ether, but was once called <i>sweet oil of vitriol</i>. Methyl phenyl ether is <a href="/wiki/Anisole" title="Anisole">anisole</a>, because it was originally found in <a href="/wiki/Aniseed" class="mw-redirect" title="Aniseed">aniseed</a>. The <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> ethers include <a href="/wiki/Furan" title="Furan">furans</a>. <a href="/wiki/Acetal" title="Acetal">Acetals</a> (α-alkoxy ethers R–CH(–OR)–O–R) are another class of ethers with characteristic properties. </p> <div class="mw-heading mw-heading3"><h3 id="Polyethers">Polyethers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=5" title="Edit section: Polyethers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyethers are generally <a href="/wiki/Polymer" title="Polymer">polymers</a> containing ether linkages in their main chain. The term <a href="/wiki/Polyol" title="Polyol">polyol</a> generally refers to polyether polyols with one or more functional <a href="/wiki/End-group" class="mw-redirect" title="End-group">end-groups</a> such as a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties. </p><p><a href="/wiki/Crown_ether" title="Crown ether">Crown ethers</a> are cyclic polyethers. Some toxins produced by <a href="/wiki/Dinoflagellate" title="Dinoflagellate">dinoflagellates</a> such as <a href="/wiki/Brevetoxin" title="Brevetoxin">brevetoxin</a> and <a href="/wiki/Ciguatoxin" title="Ciguatoxin">ciguatoxin</a> are extremely large and are known as <i>cyclic</i> or <i>ladder</i> polyethers. </p> <table class="wikitable"> <caption>Aliphatic polyethers </caption> <tbody><tr> <th>Name of the polymers with low to medium molar mass</th> <th>Name of the polymers with high molar mass</th> <th>Preparation</th> <th>Repeating unit</th> <th>Examples of trade names </th></tr> <tr> <td><a href="/wiki/Paraformaldehyde" title="Paraformaldehyde">Paraformaldehyde</a></td> <td><a href="/wiki/Polyoxymethylene_plastic" class="mw-redirect" title="Polyoxymethylene plastic">Polyoxymethylene</a> (POM) or polyacetal or polyformaldehyde</td> <td><a href="/wiki/Step-growth_polymerisation" class="mw-redirect" title="Step-growth polymerisation">Step-growth polymerisation</a> of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a></td> <td>–CH<sub>2</sub>O–</td> <td>Delrin from <a href="/wiki/DuPont" title="DuPont">DuPont</a> </td></tr> <tr> <td><a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">Polyethylene glycol</a> (PEG)</td> <td>Polyethylene oxide (PEO) or polyoxyethylene (POE)</td> <td><a href="/wiki/Ring-opening_polymerization" title="Ring-opening polymerization">Ring-opening polymerization</a> of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a></td> <td>–CH<sub>2</sub>CH<sub>2</sub>O–</td> <td>Carbowax from <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow</a> </td></tr> <tr> <td><a href="/wiki/Polypropylene_glycol" title="Polypropylene glycol">Polypropylene glycol</a> (PPG)</td> <td>Polypropylene oxide (PPOX) or polyoxypropylene (POP)</td> <td>anionic ring-opening polymerization of <a href="/wiki/Propylene_oxide" title="Propylene oxide">propylene oxide</a></td> <td>–CH<sub>2</sub>CH(CH<sub>3</sub>)O–</td> <td>Arcol from <a href="/wiki/Covestro" title="Covestro">Covestro</a> </td></tr> <tr> <td>Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG)</td> <td><a href="/wiki/Polytetrahydrofuran" title="Polytetrahydrofuran">Polytetrahydrofuran</a> (PTHF)</td> <td>Acid-catalyzed ring-opening polymerization of <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>O−</span></td> <td>Terathane from <a href="/wiki/Invista" title="Invista">Invista</a> and PolyTHF from <a href="/wiki/BASF" title="BASF">BASF</a> </td></tr></tbody></table> <p>The phenyl ether polymers are a class of <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic</a> polyethers containing aromatic cycles in their main chain: <a href="/wiki/Polyphenyl_ether" title="Polyphenyl ether">polyphenyl ether</a> (PPE) and <a href="/wiki/Poly(p-phenylene_oxide)" title="Poly(p-phenylene oxide)">poly(<i>p</i>-phenylene oxide)</a> (PPO). </p> <div class="mw-heading mw-heading3"><h3 id="Related_compounds">Related compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=6" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many classes of compounds with C–O–C linkages are not considered ethers: <a href="/wiki/Ester" title="Ester">Esters</a> (R–C(=O)–O–R′), <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetals</a> (R–CH(–OH)–O–R′), <a href="/wiki/Carboxylic_acid_anhydride" class="mw-redirect" title="Carboxylic acid anhydride">carboxylic acid anhydrides</a> (RC(=O)–O–C(=O)R′). </p><p>There are compounds which, instead of <a href="/wiki/Carbon" title="Carbon">C</a> in the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−O−C</span> linkage, contain heavier <a href="/wiki/Group_14" class="mw-redirect" title="Group 14">group 14</a> <a href="/wiki/Chemical_elements" class="mw-redirect" title="Chemical elements">chemical elements</a> (e.g., <a href="/wiki/Silicon" title="Silicon">Si</a>, <a href="/wiki/Germanium" title="Germanium">Ge</a>, <a href="/wiki/Tin" title="Tin">Sn</a>, <a href="/wiki/Lead" title="Lead">Pb</a>). Such compounds are considered ethers as well. Examples of such ethers are <a href="/wiki/Silyl_enol_ether" title="Silyl enol ether">silyl enol ethers</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">3</sub>Si−O−CR=CR<sub class="template-chem2-sub">2</sub></span> (containing the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si−O−C</span> linkage), <a href="/wiki/Disiloxane" title="Disiloxane">disiloxane</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>Si−O−SiH<sub class="template-chem2-sub">3</sub></span> (the other name of this compound is disilyl ether, containing the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si−O−Si</span> linkage) and <a href="/wiki/Stannoxane" title="Stannoxane">stannoxanes</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">3</sub>Sn−O−SnR<sub class="template-chem2-sub">3</sub></span> (containing the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn−O−Sn</span> linkage). </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=Ether&action=edit&section=7" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethers have <a href="/wiki/Boiling_point" title="Boiling point">boiling points</a> similar to those of the analogous <a href="/wiki/Alkane" title="Alkane">alkanes</a>. Simple ethers are generally colorless. </p> <table style="width:100%;" class="wikitable"> <tbody><tr style="background:#ffdead;"> <th colspan="6">Selected data about some alkyl ethers </th></tr> <tr> <th>Ether </th> <th>Structure </th> <th>m.p. (°C) </th> <th>b.p. (°C) </th> <th>Solubility in 1 liter of H<sub>2</sub>O </th> <th>Dipole moment (<a href="/wiki/Debye" title="Debye">D</a>) </th></tr> <tr> <td><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></td> <td>CH<sub>3</sub>–O–CH<sub>3</sub></td> <td>−138.5</td> <td>−23.0</td> <td>70 g</td> <td>1.30 </td></tr> <tr> <td><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></td> <td>CH<sub>3</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>3</sub></td> <td>−116.3</td> <td>34.4</td> <td>69 g</td> <td>1.14 </td></tr> <tr> <td><a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">Tetrahydrofuran</a></td> <td>O(CH<sub>2</sub>)<sub>4</sub></td> <td>−108.4</td> <td>66.0</td> <td><a href="/wiki/Miscibility" title="Miscibility">Miscible</a></td> <td>1.74 </td></tr> <tr> <td><a href="/wiki/1,4-Dioxane" title="1,4-Dioxane">Dioxane</a></td> <td>O(C<sub>2</sub>H<sub>4</sub>)<sub>2</sub>O</td> <td>11.8</td> <td>101.3</td> <td>Miscible</td> <td>0.45 </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=Ether&action=edit&section=8" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Frame"><a href="/wiki/File:Diethylether_peroxide_chemical_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/7/78/Diethylether_peroxide_chemical_structure.png" decoding="async" width="211" height="80" class="mw-file-element" data-file-width="211" data-file-height="80" /></a><figcaption>Structure of the polymeric <a href="/wiki/Diethyl_ether_peroxide" title="Diethyl ether peroxide">diethyl ether peroxide</a></figcaption></figure> <p>The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactivity</a>, they are more reactive than <a href="/wiki/Alkanes" class="mw-redirect" title="Alkanes">alkanes</a>. </p><p>Specialized ethers such as <a href="/wiki/Epoxide" title="Epoxide">epoxides</a>, <a href="/wiki/Ketal" class="mw-redirect" title="Ketal">ketals</a>, and <a href="/wiki/Acetal" title="Acetal">acetals</a> are unrepresentative classes of ethers and are discussed in separate articles. Important reactions are listed below.<sup id="cite_ref-Ullmann_4-0" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cleavage">Cleavage</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=9" title="Edit section: Cleavage"><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">See also: <a href="/wiki/Ether_cleavage" title="Ether cleavage">Ether cleavage</a></div> <p>Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and <a href="/wiki/Hydroiodic_acid" title="Hydroiodic acid">hydroiodic acid</a>. <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a> cleaves ethers only slowly. Methyl ethers typically afford <a href="/wiki/Methyl_halide" class="mw-redirect" title="Methyl halide">methyl halides</a>: </p> <dl><dd>ROCH<sub>3</sub> + HBr → CH<sub>3</sub>Br + ROH</dd></dl> <p>These reactions proceed via <a href="/wiki/Onium_compounds" class="mw-redirect" title="Onium compounds">onium</a> intermediates, i.e. [RO(H)CH<sub>3</sub>]<sup>+</sup>Br<sup>−</sup>. </p><p>Some ethers undergo rapid cleavage with <a href="/wiki/Boron_tribromide" title="Boron tribromide">boron tribromide</a> (even <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> is used in some cases) to give the alkyl bromide.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Depending on the substituents, some ethers can be cleaved with a variety of reagents, e.g. strong base. </p><p>Despite these difficulties the chemical <a href="/wiki/Pulp_(paper)" title="Pulp (paper)">paper pulping</a> processes are based on cleavage of ether bonds in the <a href="/wiki/Lignin" title="Lignin">lignin</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Peroxide_formation">Peroxide formation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=10" title="Edit section: Peroxide formation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When stored in the presence of air or oxygen, ethers tend to form <a href="/wiki/Explosive_material" class="mw-redirect" title="Explosive material">explosive</a> <a href="/wiki/Organic_peroxide" class="mw-redirect" title="Organic peroxide">peroxides</a>, such as <a href="/wiki/Diethyl_ether_hydroperoxide" class="mw-redirect" title="Diethyl ether hydroperoxide">diethyl ether hydroperoxide</a>. The reaction is accelerated by light, metal catalysts, and <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid. The presence of peroxide in old samples of ethers may be detected by shaking them with freshly prepared solution of a ferrous sulfate followed by addition of KSCN. Appearance of blood red color indicates presence of peroxides. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> (THF) or <a href="/wiki/Dimethoxyethane" title="Dimethoxyethane">ethylene glycol dimethyl ether</a> (1,2-dimethoxyethane) are avoided in industrial processes. </p> <div class="mw-heading mw-heading3"><h3 id="Lewis_bases">Lewis bases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=11" title="Edit section: Lewis bases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:CSD_CIF_CANZOG10.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/CSD_CIF_CANZOG10.png/172px-CSD_CIF_CANZOG10.png" decoding="async" width="172" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/CSD_CIF_CANZOG10.png/258px-CSD_CIF_CANZOG10.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/CSD_CIF_CANZOG10.png/344px-CSD_CIF_CANZOG10.png 2x" data-file-width="777" data-file-height="773" /></a><figcaption>Structure of VCl3(<a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">thf</a>)3.<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><style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend"><span class="legend-color mw-no-invert" style="background-color:blue; color:white;"> </span> <a href="/wiki/Vanadium" title="Vanadium">Vanadium</a>, V</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:darkgreen; color:white;"> </span> <a href="/wiki/Chlorine" title="Chlorine">Chlorine</a>, Cl</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:grey; color:black;"> </span> <a href="/wiki/Carbon" title="Carbon">Carbon</a>, C</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:white; color:black;"> </span> <a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a>, H</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend"><span class="legend-color mw-no-invert" style="background-color:red; color:black;"> </span> <a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a>, N</div></figcaption></figure> <p>Ethers serve as <a href="/wiki/Lewis_base" class="mw-redirect" title="Lewis base">Lewis bases</a>. For instance, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a> forms a <a href="/wiki/Coordination_complex" title="Coordination complex">complex</a> with <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a>, i.e. borane diethyl etherate (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BF<sub class="template-chem2-sub">3</sub>·O(CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>). Ethers also coordinate to the <a href="/wiki/Magnesium" title="Magnesium">Mg</a> center in <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a>. <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">Tetrahydrofuran</a> is more basic than <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> ethers. It forms with many <a href="/wiki/Transition_metal_ether_complex" title="Transition metal ether complex">complexes</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Alpha-halogenation">Alpha-halogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=12" title="Edit section: Alpha-halogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This reactivity is similar to the tendency of ethers with <a href="/wiki/Alpha" title="Alpha">alpha</a> hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers. </p> <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=Ether&action=edit&section=13" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Dehydration_of_alcohols">Dehydration of alcohols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=14" title="Edit section: Dehydration of alcohols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydration</a> of <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohols</a> affords ethers:<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> <dl><dd>2 R–OH → R–O–R + <a href="/wiki/Water" title="Water">H<sub>2</sub>O</a> at high temperature</dd></dl> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg/507px-Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg.png" decoding="async" width="507" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg/761px-Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg/1014px-Acid_catalysed_alchol_condensation_to_produce_symmetrical_ether.svg.png 2x" data-file-width="512" data-file-height="114" /></a><figcaption></figcaption></figure> <p>This direct nucleophilic substitution reaction requires elevated temperatures (about 125 °C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a mixture of products. Diethyl ether is produced from ethanol by this method. Cyclic ethers are readily generated by this approach. Elimination reactions compete with dehydration of the alcohol: </p> <dl><dd>R–CH<sub>2</sub>–CH<sub>2</sub>(OH) → R–CH=CH<sub>2</sub> + H<sub>2</sub>O</dd></dl> <p>The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers. </p> <div class="mw-heading mw-heading3"><h3 id="Electrophilic_addition_of_alcohols_to_alkenes">Electrophilic addition of alcohols to alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=15" title="Edit section: Electrophilic addition of alcohols to alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alcohols add to electrophilically activated <a href="/wiki/Alkene" title="Alkene">alkenes</a>. The method is atom-economical: </p> <dl><dd><a href="/wiki/Alkene" title="Alkene">R<sub>2</sub>C=CR<sub>2</sub></a> + R–OH → R<sub>2</sub>CH–C(–O–R)–R<sub>2</sub></dd></dl> <p><a href="/wiki/Acid" title="Acid">Acid</a> <a href="/wiki/Catalysis" title="Catalysis">catalysis</a> is required for this reaction. Commercially important ethers prepared in this way are derived from <a href="/wiki/Isobutene" class="mw-redirect" title="Isobutene">isobutene</a> or <a href="/wiki/Isoamylene" class="mw-redirect" title="Isoamylene">isoamylene</a>, which protonate to give relatively stable <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>. Using ethanol and methanol with these two alkenes, four fuel-grade ethers are produced: <a href="/wiki/Methyl_tert-butyl_ether" title="Methyl tert-butyl ether">methyl tert-butyl ether</a> (MTBE), <a href="/wiki/Tert-Amyl_methyl_ether" title="Tert-Amyl methyl ether">methyl tert-amyl ether</a> (TAME), <a href="/wiki/Ethyl_tert-butyl_ether" title="Ethyl tert-butyl ether">ethyl tert-butyl ether</a> (ETBE), and <a href="/w/index.php?title=Ethyl_tert-amyl_ether&action=edit&redlink=1" class="new" title="Ethyl tert-amyl ether (page does not exist)">ethyl tert-amyl ether</a> (TAEE).<sup id="cite_ref-Ullmann_4-1" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Solid_acid_catalyst" class="mw-redirect" title="Solid acid catalyst">Solid acid catalysts</a> are typically used to promote this reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Epoxides">Epoxides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=16" title="Edit section: Epoxides"><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/Epoxide" title="Epoxide">epoxide</a></div> <p><a href="/wiki/Epoxide" title="Epoxide">Epoxides</a> are typically prepared by oxidation of alkenes. The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen. Other epoxides are produced by one of two routes: </p> <ul><li>By the oxidation of alkenes with a <a href="/wiki/Peroxyacid" class="mw-redirect" title="Peroxyacid">peroxyacid</a> such as <a href="/wiki/Meta-Chloroperoxybenzoic_acid" title="Meta-Chloroperoxybenzoic acid"><i>m</i>-CPBA</a>.</li> <li>By the base intramolecular nucleophilic substitution of a <a href="/wiki/Halohydrin" title="Halohydrin">halohydrin</a>.</li></ul> <p>Many ethers, <a href="/wiki/Ethoxylate" class="mw-redirect" title="Ethoxylate">ethoxylates</a> and <a href="/wiki/Crown_ether" title="Crown ether">crown ethers</a>, are produced from epoxides. </p> <div class="mw-heading mw-heading3"><h3 id="Williamson_and_Ullmann_ether_syntheses">Williamson and Ullmann ether syntheses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=17" title="Edit section: Williamson and Ullmann ether syntheses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Nucleophilic_displacement" class="mw-redirect" title="Nucleophilic displacement">Nucleophilic displacement</a> of <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a> by <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a> </p> <dl><dd>R–ONa + R′–X → R–O–R′ + Na<a href="/wiki/Halide" title="Halide">X</a></dd></dl> <p>This reaction, the <a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a>, involves treatment of a parent <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> with a strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> to form the alkoxide, followed by addition of an appropriate <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic compound</a> bearing a suitable <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> (R–X). Although popular in textbooks, the method is usually impractical on scale because it cogenerates significant waste. </p><p>Suitable leaving groups (X) include <a href="/wiki/Iodide" title="Iodide">iodide</a>, <a href="/wiki/Bromide" title="Bromide">bromide</a>, or <a href="/wiki/Sulfonate" title="Sulfonate">sulfonates</a>. This method usually does not work well for aryl halides (e.g. <a href="/wiki/Bromobenzene" title="Bromobenzene">bromobenzene</a>, see Ullmann condensation below). Likewise, this method only gives the best yields for primary halides. Secondary and tertiary halides are prone to undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups. </p><p>In a related reaction, alkyl halides undergo nucleophilic displacement by <a href="/wiki/Phenoxide" class="mw-redirect" title="Phenoxide">phenoxides</a>. The R–X cannot be used to react with the alcohol. However <a href="/wiki/Phenols" title="Phenols">phenols</a> can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> like <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> to form phenoxide ions. The phenoxide ion will then substitute the –X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an <a href="/wiki/SN2" class="mw-redirect" title="SN2">S<sub>N</sub>2</a> mechanism. </p> <dl><dd>C<sub>6</sub>H<sub>5</sub>OH + OH<sup>−</sup> → C<sub>6</sub>H<sub>5</sub>–O<sup>−</sup> + H<sub>2</sub>O</dd> <dd>C<sub>6</sub>H<sub>5</sub>–O<sup>−</sup> + R–X → C<sub>6</sub>H<sub>5</sub>OR</dd></dl> <p>The <a href="/wiki/Ullmann_condensation" title="Ullmann condensation">Ullmann condensation</a> is similar to the Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Important_ethers">Important ethers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ether&action=edit&section=18" title="Edit section: Important ethers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Ethylene_oxide_chemical_structure.png" class="mw-file-description" title="Chemical structure of ethylene oxide"><img alt="Chemical structure of ethylene oxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Ethylene_oxide_chemical_structure.png/50px-Ethylene_oxide_chemical_structure.png" decoding="async" width="50" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Ethylene_oxide_chemical_structure.png/75px-Ethylene_oxide_chemical_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Ethylene_oxide_chemical_structure.png/100px-Ethylene_oxide_chemical_structure.png 2x" data-file-width="778" data-file-height="817" /></a></span> </td> <td><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a> </td> <td>A cyclic ether. Also the simplest <a href="/wiki/Epoxide" title="Epoxide">epoxide</a>. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Dimethylether_chemical_structure.svg" class="mw-file-description" title="Chemical structure of dimethyl ether"><img alt="Chemical structure of dimethyl ether" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Dimethylether_chemical_structure.svg/90px-Dimethylether_chemical_structure.svg.png" decoding="async" width="90" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Dimethylether_chemical_structure.svg/135px-Dimethylether_chemical_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Dimethylether_chemical_structure.svg/180px-Dimethylether_chemical_structure.svg.png 2x" data-file-width="41" data-file-height="18" /></a></span> </td> <td><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a> </td> <td>A colourless gas that is used as an <a href="/wiki/Aerosol_spray#Aerosol_propellants" class="mw-redirect" title="Aerosol spray">aerosol spray propellant</a>. A potential renewable alternative fuel for <a href="/wiki/Diesel_engine" title="Diesel engine">diesel engines</a> with a <a href="/wiki/Cetane_number" title="Cetane number">cetane rating</a> as high as 56–57. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Diethyl_ether_chemical_structure.svg" class="mw-file-description" title="Chemical structure of diethyl ether"><img alt="Chemical structure of diethyl ether" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Diethyl_ether_chemical_structure.svg/120px-Diethyl_ether_chemical_structure.svg.png" decoding="async" width="120" height="30" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Diethyl_ether_chemical_structure.svg/180px-Diethyl_ether_chemical_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Diethyl_ether_chemical_structure.svg/240px-Diethyl_ether_chemical_structure.svg.png 2x" data-file-width="69" data-file-height="17" /></a></span> </td> <td><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a> </td> <td>A colourless liquid with sweet odour. A common low boiling <a href="/wiki/Solvent" title="Solvent">solvent</a> (b.p. 34.6 °C) and an early <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a>. Used as starting fluid for diesel engines. Also used as a <a href="/wiki/Refrigerant" title="Refrigerant">refrigerant</a> and in the manufacture of <a href="/wiki/Smokeless_gunpowder" class="mw-redirect" title="Smokeless gunpowder">smokeless gunpowder</a>, along with use in <a href="/wiki/Perfumery" class="mw-redirect" title="Perfumery">perfumery</a>. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Dimethoxyethane_chemical_structure.png" class="mw-file-description" title="Chemical structure of dimethoxyethane"><img alt="Chemical structure of dimethoxyethane" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Dimethoxyethane_chemical_structure.png/140px-Dimethoxyethane_chemical_structure.png" decoding="async" width="140" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Dimethoxyethane_chemical_structure.png/210px-Dimethoxyethane_chemical_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Dimethoxyethane_chemical_structure.png/280px-Dimethoxyethane_chemical_structure.png 2x" data-file-width="1186" data-file-height="345" /></a></span> </td> <td><a href="/wiki/Dimethoxyethane" title="Dimethoxyethane">Dimethoxyethane</a> (DME) </td> <td>A water miscible solvent often found in lithium batteries (b.p. 85 °C): </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:1-4-Dioxane.svg" class="mw-file-description" title="Chemical structure of dioxane"><img alt="Chemical structure of dioxane" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/1-4-Dioxane.svg/50px-1-4-Dioxane.svg.png" decoding="async" width="50" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/1-4-Dioxane.svg/75px-1-4-Dioxane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/1-4-Dioxane.svg/100px-1-4-Dioxane.svg.png 2x" data-file-width="100" data-file-height="133" /></a></span> </td> <td><a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">Dioxane</a> </td> <td>A cyclic ether and high-boiling solvent (b.p. 101.1 °C). </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Tetrahydrofuran.svg" class="mw-file-description" title="Chemical structure of THF"><img alt="Chemical structure of THF" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydrofuran.svg/90px-Tetrahydrofuran.svg.png" decoding="async" width="90" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydrofuran.svg/135px-Tetrahydrofuran.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydrofuran.svg/180px-Tetrahydrofuran.svg.png 2x" data-file-width="429" data-file-height="451" /></a></span> </td> <td><a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">Tetrahydrofuran</a> (THF) </td> <td>A cyclic ether, one of the most polar simple ethers that is used as a solvent. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Anisole.svg" class="mw-file-description" title="Chemical structure of anisole"><img alt="Chemical structure of anisole" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Anisole.svg/90px-Anisole.svg.png" decoding="async" width="90" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Anisole.svg/135px-Anisole.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Anisole.svg/180px-Anisole.svg.png 2x" data-file-width="125" data-file-height="213" /></a></span> </td> <td><a href="/wiki/Anisole" title="Anisole">Anisole</a> (methoxybenzene) </td> <td>An <b>aryl ether</b> and a major constituent of the <a href="/wiki/Essential_oil" title="Essential oil">essential oil</a> of <a href="/wiki/Anise" title="Anise">anise</a> seed. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:18-crown-6.svg" class="mw-file-description" title="Chemical structure of 18-crown-6"><img alt="Chemical structure of 18-crown-6" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/18-crown-6.svg/150px-18-crown-6.svg.png" decoding="async" width="150" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/18-crown-6.svg/225px-18-crown-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/18-crown-6.svg/300px-18-crown-6.svg.png 2x" data-file-width="104" data-file-height="100" /></a></span> </td> <td><a href="/wiki/Crown_ether" title="Crown ether">Crown ethers</a> </td> <td>Cyclic polyethers that are used as <a href="/wiki/Phase_transfer_catalyst" class="mw-redirect" title="Phase transfer catalyst">phase transfer catalysts</a>. </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Poly(ethylene_glycol)_alternate.svg" class="mw-file-description" title="Chemical structure of polyethylene glycol"><img alt="Chemical structure of polyethylene glycol" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Poly%28ethylene_glycol%29_alternate.svg/150px-Poly%28ethylene_glycol%29_alternate.svg.png" decoding="async" width="150" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Poly%28ethylene_glycol%29_alternate.svg/225px-Poly%28ethylene_glycol%29_alternate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Poly%28ethylene_glycol%29_alternate.svg/300px-Poly%28ethylene_glycol%29_alternate.svg.png 2x" data-file-width="325" data-file-height="195" /></a></span> </td> <td><a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">Polyethylene glycol</a> (PEG) </td> <td>A linear polyether, e.g. used in <a href="/wiki/Cosmetics" title="Cosmetics">cosmetics</a> and <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">pharmaceuticals</a>. </td></tr> <tr> <td> </td> <td><a href="/wiki/Polypropylene_glycol" title="Polypropylene glycol">Polypropylene glycol</a> </td> <td>A linear polyether, e.g. used in <a href="/wiki/Polyurethanes" class="mw-redirect" title="Polyurethanes">polyurethanes</a>. </td></tr> <tr> <td><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Platelet-activating_factor.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Platelet-activating_factor.svg/512px-Platelet-activating_factor.svg.png" decoding="async" width="512" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Platelet-activating_factor.svg/768px-Platelet-activating_factor.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Platelet-activating_factor.svg/1024px-Platelet-activating_factor.svg.png 2x" data-file-width="512" data-file-height="102" /></a></span> </td> <td>Platelet-activating factor </td> <td>An <a href="/wiki/Ether_lipid" title="Ether lipid">ether lipid</a>, an example with an ether on sn-1, an ester on sn-2, and an inorganic ether on sn-3 of the glyceryl scaffold. </td></tr></tbody></table> <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=Ether&action=edit&section=19" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Ester" title="Ester">Ester</a></li> <li><a href="/wiki/Ether_lipid" title="Ether lipid">Ether lipid</a></li> <li><a href="/wiki/Ether_addiction" title="Ether addiction">Ether addiction</a></li> <li><a href="/wiki/Ether_(song)" title="Ether (song)">Ether (song)</a></li> <li><a href="/wiki/History_of_general_anesthesia" title="History of general anesthesia">History of general anesthesia</a></li> <li><a href="/wiki/Inhalant" title="Inhalant">Inhalant</a></li> <li>Chemical paper pulping processes: <a href="/wiki/Kraft_process" title="Kraft process">Kraft process</a> (and <a href="/wiki/Soda_pulping" title="Soda pulping">Soda pulping</a>), <a href="/wiki/Organosolv" title="Organosolv">Organosolv</a> pulping process and the <a href="/wiki/Sulfite_process" title="Sulfite process">Sulfite process</a></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=Ether&action=edit&section=20" 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"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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/E02221.html">ethers</a>". <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><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.E02221">10.1351/goldbook.E02221</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaul_Patai1967" class="citation book cs1">Saul Patai, ed. (1967). <i>The Ether Linkage</i>. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. <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%2F9780470771075">10.1002/9780470771075</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77107-5" title="Special:BookSources/978-0-470-77107-5"><bdi>978-0-470-77107-5</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+Ether+Linkage&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=1967&rft_id=info%3Adoi%2F10.1002%2F9780470771075&rft.isbn=978-0-470-77107-5&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVojinovićLosehandMitzel2004" class="citation journal cs1">Vojinović, Krunoslav; Losehand, Udo; Mitzel, Norbert W. (2004). "Dichlorosilane–Dimethyl Ether Aggregation: A New Motif in Halosilane Adduct Formation". <i>Dalton Trans.</i> (16): 2578–2581. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb405684a">10.1039/b405684a</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/15303175">15303175</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Dalton+Trans.&rft.atitle=Dichlorosilane%E2%80%93Dimethyl+Ether+Aggregation%3A+A+New+Motif+in+Halosilane+Adduct+Formation&rft.issue=16&rft.pages=2578-2581&rft.date=2004&rft_id=info%3Adoi%2F10.1039%2Fb405684a&rft_id=info%3Apmid%2F15303175&rft.aulast=Vojinovi%C4%87&rft.aufirst=Krunoslav&rft.au=Losehand%2C+Udo&rft.au=Mitzel%2C+Norbert+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" in <i>Ullmann's Encyclopedia of Industrial Chemistry</i> Wiley-VCH, Weinheim, 2002. <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/10.1002%2F14356007.a10_023">10.1002/14356007.a10_023</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._F._W._McOmie_and_D._E._West1973" class="citation journal cs1">J. F. W. McOmie and D. E. West (1973). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV5P0412">"3,3′-Dihydroxylbiphenyl"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></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=3%2C3%E2%80%B2-Dihydroxylbiphenyl&rft.date=1973&rft.au=J.+F.+W.+McOmie+and+D.+E.+West&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3DCV5P0412&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 5, p. 412</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=412&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" 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="CITEREFF.A.CottonS.A.DurajG.L.PowellW.J.Roth1986" class="citation journal cs1">F.A.Cotton; S.A.Duraj; G.L.Powell; W.J.Roth (1986). "Comparative Structural Studies of the First Row Early Transition Metal(III) Chloride Tetrahydrofuran Solvates". <i>Inorg. Chim. Acta</i>. <b>113</b>: 81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0020-1693%2800%2986863-2">10.1016/S0020-1693(00)86863-2</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorg.+Chim.+Acta&rft.atitle=Comparative+Structural+Studies+of+the+First+Row+Early+Transition+Metal%28III%29+Chloride+Tetrahydrofuran+Solvates&rft.volume=113&rft.pages=81&rft.date=1986&rft_id=info%3Adoi%2F10.1016%2FS0020-1693%2800%2986863-2&rft.au=F.A.Cotton&rft.au=S.A.Duraj&rft.au=G.L.Powell&rft.au=W.J.Roth&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" 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="CITEREFClaydenGreevesWarren2001" class="citation book cs1">Clayden; Greeves; Warren (2001). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00clay_0/page/129"><i>Organic chemistry</i></a></span>. Oxford University Press. p. <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00clay_0/page/129">129</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-850346-0" title="Special:BookSources/978-0-19-850346-0"><bdi>978-0-19-850346-0</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=129&rft.pub=Oxford+University+Press&rft.date=2001&rft.isbn=978-0-19-850346-0&rft.au=Clayden&rft.au=Greeves&rft.au=Warren&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganicchemistry00clay_0%2Fpage%2F129&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrlanKikelj2006" class="citation journal cs1">Frlan, Rok; Kikelj, Danijel (29 June 2006). "Recent Progress in Diaryl Ether Synthesis". <i>Synthesis</i>. <b>2006</b> (14): 2271–2285. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2006-942440">10.1055/s-2006-942440</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synthesis&rft.atitle=Recent+Progress+in+Diaryl+Ether+Synthesis&rft.volume=2006&rft.issue=14&rft.pages=2271-2285&rft.date=2006-06-29&rft_id=info%3Adoi%2F10.1055%2Fs-2006-942440&rft.aulast=Frlan&rft.aufirst=Rok&rft.au=Kikelj%2C+Danijel&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEther" 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><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_groups" 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"><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: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_groups" 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 href="/wiki/Alkene" title="Alkene">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 class="mw-selflink selflink">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/Phosphorus" title="Phosphorus">Phosphorus</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/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-odd" 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/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</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-even" 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-odd" 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></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-even" 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></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"><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/Q103230#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata" 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/Q103230#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata" 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/Q103230#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/915813/">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/4070978-4">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85045088">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Éthers"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb121494550">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Éthers"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb121494550">BnF data</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="ethery"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph241924&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007555681805171">Israel</a></span></li></ul></div></td></tr></tbody></table></div></div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" 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=Ether&oldid=1259858737">https://en.wikipedia.org/w/index.php?title=Ether&oldid=1259858737</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">Categories</a>: <ul><li><a href="/wiki/Category:Ethers" title="Category:Ethers">Ethers</a></li><li><a href="/wiki/Category:Functional_groups" title="Category:Functional groups">Functional groups</a></li><li><a href="/wiki/Category:Impression_material" title="Category:Impression material">Impression material</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></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 November 2024, at 13:26<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=Ether&curid=9263&diff=1259858737&oldid=1259809383&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://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></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"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-6df7948d6c-cqfcr","wgBackendResponseTime":248,"wgPageParseReport":{"limitreport":{"cputime":"0.460","walltime":"0.593","ppvisitednodes":{"value":2588,"limit":1000000},"postexpandincludesize":{"value":61705,"limit":2097152},"templateargumentsize":{"value":2552,"limit":2097152},"expansiondepth":{"value":12,"limit":100},"expensivefunctioncount":{"value":6,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":52854,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 472.736 1 -total"," 35.68% 168.658 1 Template:Reflist"," 18.95% 89.569 1 Template:Functional_Groups"," 18.37% 86.851 3 Template:Navbox"," 13.86% 65.516 1 Template:Short_description"," 12.45% 58.862 2 Template:Cite_book"," 11.54% 54.562 1 Template:GoldBookRef"," 10.48% 49.528 1 Template:Authority_control"," 9.95% 47.049 2 Template:Doi"," 8.91% 42.121 2 Template:Pagetype"]},"scribunto":{"limitreport-timeusage":{"value":"0.258","limit":"10.000"},"limitreport-memusage":{"value":6108652,"limit":52428800}},"cachereport":{"origin":"mw-api-ext.codfw.main-67468f59cb-p5d2w","timestamp":"20241127132643","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Ether","url":"https:\/\/en.wikipedia.org\/wiki\/Ether","sameAs":"http:\/\/www.wikidata.org\/entity\/Q103230","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q103230","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":"2001-11-04T11:48:02Z","dateModified":"2024-11-27T13:26:45Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/7\/78\/Ether-%28general%29.svg","headline":"class of organic compounds containing oxygen connected to two organyl groups"}</script> </body> </html>