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class="vector-toc-numb">2</span> <span>Properties</span> </div> </a> <button aria-controls="toc-Properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Properties subsection</span> </button> <ul id="toc-Properties-sublist" class="vector-toc-list"> <li id="toc-Table_of_cycloalkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Table_of_cycloalkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Table of cycloalkanes</span> </div> </a> <ul id="toc-Table_of_cycloalkanes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Conformations_and_ring_strain" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Conformations_and_ring_strain"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Conformations and ring strain</span> </div> </a> <ul id="toc-Conformations_and_ring_strain-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> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Preparation</span> </div> </a> <ul id="toc-Preparation-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">6</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">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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"><span class="mw-page-title-main">Cycloalkane</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 51 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-51" 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">51 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/Sikloalkaan" title="Sikloalkaan – Afrikaans" lang="af" hreflang="af" data-title="Sikloalkaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D8%A7%D9%86_%D8%AD%D9%84%D9%82%D9%8A" title="ألكان حلقي – Arabic" lang="ar" hreflang="ar" data-title="ألكان حلقي" 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/Sikloalkanlar" title="Sikloalkanlar – Azerbaijani" lang="az" hreflang="az" data-title="Sikloalkanlar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A6%D1%8B%D0%BA%D0%BB%D1%8F%D0%B0%D0%BB%D1%8C%D0%BA%D0%B0%D0%BD%D1%8B" title="Цыкляальканы – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Цыкляальканы" 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-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Циклоалкан – Bulgarian" lang="bg" hreflang="bg" data-title="Циклоалкан" 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/Cikloalkani" title="Cikloalkani – Bosnian" lang="bs" hreflang="bs" data-title="Cikloalkani" 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/Cicloalc%C3%A0" title="Cicloalcà – Catalan" lang="ca" hreflang="ca" data-title="Cicloalcà" 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/Cykloalkany" title="Cykloalkany – Czech" lang="cs" hreflang="cs" data-title="Cykloalkany" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cycloalkane" title="Cycloalkane – German" lang="de" hreflang="de" data-title="Cycloalkane" 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/Ts%C3%BCkloalkaanid" title="Tsükloalkaanid – Estonian" lang="et" hreflang="et" data-title="Tsükloalkaanid" 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%9A%CF%85%CE%BA%CE%BB%CE%BF%CE%B1%CE%BB%CE%BA%CE%AC%CE%BD%CE%B9%CE%B1" title="Κυκλοαλκάνια – Greek" lang="el" hreflang="el" data-title="Κυκλοαλκάνια" 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/Cicloalcano" title="Cicloalcano – Spanish" lang="es" hreflang="es" data-title="Cicloalcano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zikloalkano" title="Zikloalkano – Basque" lang="eu" hreflang="eu" data-title="Zikloalkano" 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%B3%DB%8C%DA%A9%D9%84%D9%88%D8%A2%D9%84%DA%A9%D8%A7%D9%86" title="سیکلوآلکان – Persian" lang="fa" hreflang="fa" data-title="سیکلوآلکان" 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/Cycloalcane" title="Cycloalcane – French" lang="fr" hreflang="fr" data-title="Cycloalcane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A1%9C%EC%95%8C%EC%BC%80%EC%9D%B8" title="사이클로알케인 – Korean" lang="ko" hreflang="ko" data-title="사이클로알케인" 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/%D5%91%D5%AB%D5%AF%D5%AC%D5%B8%D5%BA%D5%A1%D6%80%D5%A1%D6%86%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Ցիկլոպարաֆիններ – Armenian" lang="hy" hreflang="hy" data-title="Ցիկլոպարաֆիններ" 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%B8%E0%A4%BE%E0%A4%87%E0%A4%95%E0%A5%8D%E0%A4%B2%E0%A5%8B%E0%A4%85%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%87%E0%A4%A8" title="साइक्लोअल्केन – Hindi" lang="hi" hreflang="hi" data-title="साइक्लोअल्केन" 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/Cikloalkani" title="Cikloalkani – Croatian" lang="hr" hreflang="hr" data-title="Cikloalkani" 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/Sikloalkana" title="Sikloalkana – Indonesian" lang="id" hreflang="id" data-title="Sikloalkana" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cicloalcani" title="Cicloalcani – Italian" lang="it" hreflang="it" data-title="Cicloalcani" 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%A6%D7%99%D7%A7%D7%9C%D7%95%D7%90%D7%9C%D7%A7%D7%90%D7%9F" title="ציקלואלקאן – Hebrew" lang="he" hreflang="he" data-title="ציקלואלקאן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AA%E1%83%98%E1%83%99%E1%83%9A%E1%83%9D%E1%83%90%E1%83%9A%E1%83%99%E1%83%90%E1%83%9C%E1%83%98" title="ციკლოალკანი – Georgian" lang="ka" hreflang="ka" data-title="ციკლოალკანი" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D0%B4%D0%B0%D1%80" title="Циклоалкандар – Kazakh" lang="kk" hreflang="kk" data-title="Циклоалкандар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Cikloalkanai" title="Cikloalkanai – Lithuanian" lang="lt" hreflang="lt" data-title="Cikloalkanai" 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/Cikloalk%C3%A1nok" title="Cikloalkánok – Hungarian" lang="hu" hreflang="hu" data-title="Cikloalkánok" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Циклоалкан – Macedonian" lang="mk" hreflang="mk" data-title="Циклоалкан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Циклоалкан – Mongolian" lang="mn" hreflang="mn" data-title="Циклоалкан" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cycloalkaan" title="Cycloalkaan – Dutch" lang="nl" hreflang="nl" data-title="Cycloalkaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%82%AF%E3%83%AD%E3%82%A2%E3%83%AB%E3%82%AB%E3%83%B3" title="シクロアルカン – Japanese" lang="ja" hreflang="ja" data-title="シクロアルカン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Sykloalkan" title="Sykloalkan – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Sykloalkan" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Naftenlar" title="Naftenlar – Uzbek" lang="uz" hreflang="uz" data-title="Naftenlar" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cykloalkany" title="Cykloalkany – Polish" lang="pl" hreflang="pl" data-title="Cykloalkany" 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/Cicloalcano" title="Cicloalcano – Portuguese" lang="pt" hreflang="pt" data-title="Cicloalcano" 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/Cicloalcan" title="Cicloalcan – Romanian" lang="ro" hreflang="ro" data-title="Cicloalcan" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Циклоалканы – Russian" lang="ru" hreflang="ru" data-title="Циклоалканы" 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/Cikloalkan" title="Cikloalkan – Albanian" lang="sq" hreflang="sq" data-title="Cikloalkan" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cycloalkane" title="Cycloalkane – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cycloalkane" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cykloalk%C3%A1n" title="Cykloalkán – Slovak" lang="sk" hreflang="sk" data-title="Cykloalkán" 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/Cikloalkan" title="Cikloalkan – Slovenian" lang="sl" hreflang="sl" data-title="Cikloalkan" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D9%84%DA%A9%D8%A7%D9%86%DB%8C_%D8%A6%DB%95%DA%B5%D9%82%DB%95%DB%8C%DB%8C" title="ئەلکانی ئەڵقەیی – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەلکانی ئەڵقەیی" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Циклоалкан – Serbian" lang="sr" hreflang="sr" data-title="Циклоалкан" 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/Cikloalkani" title="Cikloalkani – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cikloalkani" 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/Sykloalkaanit" title="Sykloalkaanit – Finnish" lang="fi" hreflang="fi" data-title="Sykloalkaanit" 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/Cykloalkan" title="Cykloalkan – Swedish" lang="sv" hreflang="sv" data-title="Cykloalkan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Tsikloparafinnar" title="Tsikloparafinnar – Tatar" lang="tt" hreflang="tt" data-title="Tsikloparafinnar" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li 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searchaux" style="display:none">Saturated alicyclic hydrocarbon</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclobutane-buckled-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Cyclobutane-buckled-3D-balls.png/220px-Cyclobutane-buckled-3D-balls.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Cyclobutane-buckled-3D-balls.png/330px-Cyclobutane-buckled-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Cyclobutane-buckled-3D-balls.png/440px-Cyclobutane-buckled-3D-balls.png 2x" data-file-width="1098" data-file-height="1100" /></a><figcaption>Ball-and-stick model of <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, the <b>cycloalkanes</b> (also called <b>naphthenes</b>, but distinct from <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>) are the <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">monocyclic</a> <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated</a> <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a>.<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> In other words, a cycloalkane consists only of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms arranged in a structure containing a single ring (possibly with <a href="/wiki/Side_chains" class="mw-redirect" title="Side chains">side chains</a>), and all of the carbon-carbon bonds are <a href="/wiki/Single_bond" title="Single bond">single</a>. The larger cycloalkanes, with more than 20 carbon atoms are typically called <i><b>cycloparaffins</b></i>. All cycloalkanes are isomers of <a href="/wiki/Alkanes" class="mw-redirect" title="Alkanes">alkanes</a>.<sup id="cite_ref-MSU_2-0" class="reference"><a href="#cite_note-MSU-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The cycloalkanes without side chains (also known as <b>monocycloalkanes</b>) are classified as small (<a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a> and <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a>), common (<a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a>, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>, and <a href="/wiki/Cycloheptane" title="Cycloheptane">cycloheptane</a>), medium (<a href="/wiki/Cyclooctane" title="Cyclooctane">cyclooctane</a> through <a href="/wiki/Cyclotridecane" title="Cyclotridecane">cyclotridecane</a>), and large (all the rest). </p><p>Besides this standard definition by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">the International Union of Pure and Applied Chemistry</a> (IUPAC), in some authors' usage the term <i>cycloalkane</i> includes also those saturated hydrocarbons that are polycyclic.<sup id="cite_ref-MSU_2-1" class="reference"><a href="#cite_note-MSU-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In any case, the general form of the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> for cycloalkanes is C<sub><i>n</i></sub>H<sub>2(<i>n</i>+1−<i>r</i>)</sub>, where <i>n</i> is the number of carbon atoms and <i>r</i> is the number of rings. The simpler form for cycloalkanes with only one ring is C<sub><i>n</i></sub>H<sub>2<i>n</i></sub>. </p> <meta property="mw:PageProp/toc" /> <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=Cycloalkane&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">See also: <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a></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/Alkanes" class="mw-redirect" title="Alkanes">Alkanes</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Norbornane-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Norbornane-2D-skeletal.png/220px-Norbornane-2D-skeletal.png" decoding="async" width="220" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Norbornane-2D-skeletal.png/330px-Norbornane-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Norbornane-2D-skeletal.png/440px-Norbornane-2D-skeletal.png 2x" data-file-width="689" data-file-height="601" /></a><figcaption><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (also called <i>bicyclo[2.2.1]heptane</i>)</figcaption></figure> <p>Unsubstituted cycloalkanes that contain a single ring in their molecular structure are typically named by adding the prefix "cyclo" to the name of the corresponding linear <a href="/wiki/Alkane" title="Alkane">alkane</a> with the same number of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms in its chain as the cycloalkane has in its ring. For example, the name of <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a> (C<sub>3</sub>H<sub>6</sub>) containing a three-membered ring is derived from <a href="/wiki/Propane" title="Propane">propane</a> (C<sub>3</sub>H<sub>8</sub>) - an <a href="/wiki/Alkane" title="Alkane">alkane</a> having three <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms in the main chain. </p><p>The naming of polycyclic alkanes such as <a href="/wiki/Bicyclic_compound" class="mw-redirect" title="Bicyclic compound">bicyclic</a> alkanes and <a href="/wiki/Spiro_compound" title="Spiro compound">spiro</a> alkanes is more complex, with the base name indicating the number of carbons in the ring system, a prefix indicating the number of rings ( "<i>bicyclo</i>-" or "<i>spiro</i>-"), and a numeric prefix before that indicating the number of carbons in each part of each ring, exclusive of junctions. For instance, a bicyclooctane that consists of a six-membered ring and a four-membered ring, which share two adjacent carbon atoms that form a shared edge, is [4.2.0]-bicyclooctane. That part of the six-membered ring, exclusive of the shared edge has 4 carbons. That part of the four-membered ring, exclusive of the shared edge, has 2 carbons. The edge itself, exclusive of the two vertices that define it, has 0 carbons. </p><p>There is more than one convention (method or nomenclature) for the naming of compounds, which can be confusing for those who are just learning, and inconvenient for those who are well-rehearsed in the older ways. For beginners, it is best to learn IUPAC nomenclature from <a href="/wiki/IUPAC_Blue_Book" class="mw-redirect" title="IUPAC Blue Book">a source that is up to date</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> because this system is constantly being revised. In the above example [4.2.0]-bicyclooctane would be written bicyclo[4.2.0]octane to fit the conventions for IUPAC naming. It then has room for an additional numerical prefix if there is the need to include details of other attachments to the molecule such as chlorine or a methyl group. Another convention for the naming of compounds is the <i>common name</i>, which is a shorter name and it gives less information about the compound. An example of a common name is <a href="/wiki/Terpineol" title="Terpineol">terpineol</a>, the name of which can tell us only that it is an alcohol (because the suffix "-ol" is in the name) and it should then have a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> (–OH) attached to it. </p><p>The IUPAC naming system for organic compounds can be demonstrated using the example provided in the adjacent image. The base name of the compound, indicating the total number of carbons in both rings (including the shared edge), is listed first. For instance, "heptane" denotes "hepta-", which refers to the seven carbons, and "-ane", indicating single bonding between carbons. Next, the numerical prefix is added in front of the base name, representing the number of carbons in each ring (excluding the shared carbons) and the number of carbons present in the bridge between the rings. In this example, there are two rings with two carbons each and a single bridge with one carbon, excluding the carbons shared by both the rings. The prefix consists of three numbers that are arranged in descending order, separated by dots: [2.2.1]. Before the numerical prefix is another prefix indicating the number of rings (e.g., "bicyclo+"). Thus, the name is bicyclo[2.2.1]heptane. </p><p>Cycloalkanes as a group are also known as <b>naphthenes</b>, a term mainly used in the <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> industry.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=2" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Table_of_cycloalkanes">Table of cycloalkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=3" title="Edit section: Table of cycloalkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Alkane </th> <th>Formula </th> <th>Boiling point [°C] </th> <th>Melting point [°C] </th> <th>Liquid density [g·cm<sup>−3</sup>] (at 20 °C) </th></tr> <tr> <td><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a> </td> <td>C<sub>3</sub>H<sub>6</sub> </td> <td>−33 </td> <td>−128 </td> <td> </td></tr> <tr> <td><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a> </td> <td>C<sub>4</sub>H<sub>8</sub> </td> <td>12.5 </td> <td>−91 </td> <td>0.720 </td></tr> <tr> <td><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a> </td> <td>C<sub>5</sub>H<sub>10</sub> </td> <td>49.2 </td> <td>−93.9 </td> <td>0.751 </td></tr> <tr> <td><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a> </td> <td>C<sub>6</sub>H<sub>12</sub> </td> <td>80.7 </td> <td>6.5 </td> <td>0.778 </td></tr> <tr> <td><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a> </td> <td>C<sub>7</sub>H<sub>14</sub> </td> <td>118.4 </td> <td>−12 </td> <td>0.811 </td></tr> <tr> <td><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a> </td> <td>C<sub>8</sub>H<sub>16</sub> </td> <td>149 </td> <td>14.6 </td> <td>0.834 </td></tr> <tr> <td><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a> </td> <td>C<sub>9</sub>H<sub>18</sub> </td> <td>169 </td> <td>10-11 </td> <td>0.8534 </td></tr> <tr> <td><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a> </td> <td>C<sub>10</sub>H<sub>20</sub> </td> <td>201 </td> <td>9-10 </td> <td>0.871 </td></tr></tbody></table> <p>Cycloalkanes are similar to alkanes in their general physical properties, but they have higher <a href="/wiki/Boiling_point" title="Boiling point">boiling points</a>, <a href="/wiki/Melting_point" title="Melting point">melting points</a>, and <a href="/wiki/Density" title="Density">densities</a> than alkanes. This is due to stronger <a href="/wiki/London_forces" class="mw-redirect" title="London forces">London forces</a> because the ring shape allows for a larger area of contact. Containing only C–C and C–H bonds, unreactivity of cycloalkanes with little or no <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a> (see below) are comparable to non-cyclic alkanes. </p> <div class="mw-heading mw-heading2"><h2 id="Conformations_and_ring_strain">Conformations and ring strain</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=4" title="Edit section: Conformations and ring strain"><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/Strain_(chemistry)" title="Strain (chemistry)">Strain (chemistry)</a></div> <p>In cycloalkanes, the carbon atoms are <i>sp</i><sup>3</sup> <a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">hybridized</a>, which would imply an ideal <a href="/wiki/Tetrahedral_molecular_geometry#Tetrahedral_bond_angle" title="Tetrahedral molecular geometry">tetrahedral bond angle</a> of 109° 28′ whenever possible. Owing to evident geometrical reasons, rings with 3, 4, and (to a small extent) also 5 atoms can only afford narrower angles; the consequent deviation from the ideal tetrahedral bond angles causes an increase in potential energy and an overall destabilizing effect. Eclipsing of hydrogen atoms is an important destabilizing effect, as well. The <a href="/wiki/Ring_strain#Angle_strain_(Baeyer_strain)" title="Ring strain">strain energy</a> of a cycloalkane is the increase in energy caused by the compound's geometry, and is calculated by comparing the experimental <a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">standard enthalpy change of combustion</a> of the cycloalkane with the value calculated using average bond energies. Molecular mechanics calculations are well suited to identify the many conformations occurring particularly in medium rings.<sup id="cite_ref-Dragojlovic_5-0" class="reference"><a href="#cite_note-Dragojlovic-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 16–23">: 16–23 </span></sup> </p><p>Ring strain is highest for <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>, in which the carbon atoms form a triangle and therefore have 60 °C–C–C bond angles. There are also three pairs of eclipsed hydrogens. The ring strain is calculated to be around 120 kJ mol<sup>−1</sup>. </p><p><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a> has the carbon atoms in a puckered square with approximately 90° bond angles; "puckering" reduces the eclipsing interactions between hydrogen atoms. Its ring strain is therefore slightly less, at around 110 kJ mol<sup>−1</sup>. </p><p>For a theoretical planar <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a> the C–C–C bond angles would be 108°, very close to the measure of the tetrahedral angle. Actual cyclopentane molecules are puckered, but this changes only the bond angles slightly so that angle strain is relatively small. The eclipsing interactions are also reduced, leaving a ring strain of about 25 kJ mol<sup>−1</sup>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> the ring strain and eclipsing interactions are negligible because the puckering of the ring allows ideal tetrahedral bond angles to be achieved. In the most stable <i>chair form</i> of cyclohexane, axial hydrogens on adjacent carbon atoms are pointed in opposite directions, virtually eliminating eclipsing strain. In medium-sized rings (7 to 13 carbon atoms) conformations in which the angle strain is minimised create <a href="/wiki/Transannular_strain" class="mw-redirect" title="Transannular strain">transannular strain</a> or <a href="/wiki/Pitzer_strain" class="mw-redirect" title="Pitzer strain">Pitzer strain</a>. At these ring sizes, one or more of these sources of strain must be present, resulting in an increase in strain energy, which peaks at 9 carbons (around 50 kJ mol<sup>−1</sup>). After that, strain energy slowly decreases until 12 carbon atoms, where it drops significantly; at 14, another significant drop occurs and the strain is on a level comparable with 10 kJ mol<sup>−1</sup>. At larger ring sizes there is little or no strain since there are many accessible conformations corresponding to a diamond lattice.<sup id="cite_ref-Dragojlovic_5-1" class="reference"><a href="#cite_note-Dragojlovic-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Ring strain can be considerably higher in <a href="/wiki/Bicyclic_molecule" title="Bicyclic molecule">bicyclic systems</a>. For example, <a href="/wiki/Bicyclobutane" title="Bicyclobutane">bicyclobutane</a>, C<sub>4</sub>H<sub>6</sub>, is noted for being one of the most strained compounds that is isolatable on a large scale; its strain energy is estimated at 267 kJ mol<sup>−1</sup>.<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><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="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=5" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cycloalkanes, referred to as naphthenes, are a major substrate for the catalytic reforming process.<sup id="cite_ref-Ullmann_9-0" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In the presence of a catalyst and at temperatures of about 495 to 525 °C, naphthenes undergo <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a> to give aromatic derivatives: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:KatReforming1.svg" class="mw-file-description" title="noice"><img alt="noice" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/KatReforming1.svg/300px-KatReforming1.svg.png" decoding="async" width="300" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/KatReforming1.svg/450px-KatReforming1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/KatReforming1.svg/600px-KatReforming1.svg.png 2x" data-file-width="507" data-file-height="177" /></a><figcaption>noice</figcaption></figure> <p>The process provides a way to produce high octane gasoline. </p><p>In another major industrial process, cyclohexanol is produced by the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> in air, typically using cobalt <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a>:<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>2 C<sub>6</sub>H<sub>12</sub> + O<sub>2</sub> → 2 C<sub>6</sub>H<sub>11</sub>OH</dd></dl> <p>This process coforms <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a>, used to make <a href="/wiki/Nylon" title="Nylon">nylon</a>. </p><p>The small cycloalkanes – in particular, cyclopropane – have a lower stability due to <a href="/wiki/Baeyer_strain_theory" class="mw-redirect" title="Baeyer strain theory">Baeyer strain</a> and <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a>. They react similarly to <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a>, though they do not react in <a href="/wiki/Electrophilic_addition" title="Electrophilic addition">electrophilic addition</a>, but in <a href="/wiki/Nucleophilic_aliphatic_substitution" class="mw-redirect" title="Nucleophilic aliphatic substitution">nucleophilic aliphatic substitution</a>. These reactions are ring-opening reactions or ring-cleavage reactions of <a href="/wiki/Alkyl_cycloalkane" title="Alkyl cycloalkane">alkyl cycloalkanes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=6" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many simple cycloalkanes are obtained from petroleum. They can be produced by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of unsaturated, even aromatic precursors. </p><p>Numerous methods exist for preparing cycloalkanes by ring-closing reactions of difunctional precursors. For example, diesters are cyclized in the <a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a>: </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DieckmannCondensation.png" class="mw-file-description" title="The Dieckmann condensation"><img alt="The Dieckmann condensation" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/DieckmannCondensation.png/290px-DieckmannCondensation.png" decoding="async" width="290" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/DieckmannCondensation.png/435px-DieckmannCondensation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/DieckmannCondensation.png/580px-DieckmannCondensation.png 2x" data-file-width="860" data-file-height="312" /></a><figcaption>The Dieckmann condensation</figcaption></figure></dd></dl> <p>The <a href="/wiki/Acyloin_condensation" title="Acyloin condensation">acyloin condensation</a> can be deployed similarly. </p><p>For larger rings (<a href="/wiki/Macrocyclization" class="mw-redirect" title="Macrocyclization">macrocyclizations</a>) more elaborate methods are required since intramolecular ring closure competes with intermolecular reactions. </p> <dl><dd><figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:MusconeViaRCM_(cropped).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/MusconeViaRCM_%28cropped%29.svg/242px-MusconeViaRCM_%28cropped%29.svg.png" decoding="async" width="242" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/MusconeViaRCM_%28cropped%29.svg/363px-MusconeViaRCM_%28cropped%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/MusconeViaRCM_%28cropped%29.svg/484px-MusconeViaRCM_%28cropped%29.svg.png 2x" data-file-width="242" data-file-height="104" /></a><figcaption></figcaption></figure></dd></dl> <p>The <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a>, a [4+2] cycloaddition, provides a route to cyclohexenes: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Diels-alder-stereospecificity_(cropped).png" class="mw-file-description" title="The Dieckmann condensation"><img alt="The Dieckmann condensation" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Diels-alder-stereospecificity_%28cropped%29.png/290px-Diels-alder-stereospecificity_%28cropped%29.png" decoding="async" width="290" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Diels-alder-stereospecificity_%28cropped%29.png/435px-Diels-alder-stereospecificity_%28cropped%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Diels-alder-stereospecificity_%28cropped%29.png/580px-Diels-alder-stereospecificity_%28cropped%29.png 2x" data-file-width="3526" data-file-height="1147" /></a><figcaption>The Dieckmann condensation</figcaption></figure> <p>The corresponding [2+2] cycloaddition reactions, which usually require photochemical activation, result in cyclobutanes. </p> <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=Cycloalkane&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Prelog_strain" title="Prelog strain">Prelog strain</a></li> <li><a href="/wiki/Conformational_isomerism" title="Conformational isomerism">Conformational isomerism</a></li> <li><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkene</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=Cycloalkane&action=edit&section=8" 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. 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Retrieved <span class="nowrap">2022-02-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www2.chemistry.msu.edu&rft.atitle=Alkanes+%26+Cycloalkanes&rft_id=https%3A%2F%2Fwww2.chemistry.msu.edu%2Ffaculty%2Freusch%2Fvirttxtjml%2Fchapt5.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/BlueBook/PDF/">"Blue Book"</a>. <i>iupac.qmul.ac.uk</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2023-04-01</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=iupac.qmul.ac.uk&rft.atitle=Blue+Book&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2FBlueBook%2FPDF%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFahimMA2010" class="citation book cs1">Fahim, MA, et al. (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=UcFsv1mMFHIC&q=naphthenes"><i>Fundamentals of Petroleum Refining</i></a>. p. 14. <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%2FC2009-0-16348-1">10.1016/C2009-0-16348-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-52785-1" title="Special:BookSources/978-0-444-52785-1"><bdi>978-0-444-52785-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fundamentals+of+Petroleum+Refining&rft.pages=14&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2FC2009-0-16348-1&rft.isbn=978-0-444-52785-1&rft.au=Fahim&rft.au=MA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUcFsv1mMFHIC%26q%3Dnaphthenes&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" class="Z3988"></span></span> </li> <li id="cite_note-Dragojlovic-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dragojlovic_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dragojlovic_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDragojlovic2015" class="citation journal cs1">Dragojlovic, Veljko (2015). <a rel="nofollow" class="external text" href="https://link.springer.com/content/pdf/10.1007/s40828-015-0014-0.pdf">"Conformational analysis of cycloalkanes"</a> <span class="cs1-format">(PDF)</span>. <i>Chemtexts</i>. <b>1</b> (3). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs40828-015-0014-0">10.1007/s40828-015-0014-0</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:94348487">94348487</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemtexts&rft.atitle=Conformational+analysis+of+cycloalkanes&rft.volume=1&rft.issue=3&rft.date=2015&rft_id=info%3Adoi%2F10.1007%2Fs40828-015-0014-0&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A94348487%23id-name%3DS2CID&rft.aulast=Dragojlovic&rft.aufirst=Veljko&rft_id=https%3A%2F%2Flink.springer.com%2Fcontent%2Fpdf%2F10.1007%2Fs40828-015-0014-0.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" 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="CITEREFMcMurry2000" class="citation book cs1">McMurry, John (2000). <i>Organic chemistry</i> (5th ed.). Pacific Grove, CA: Brooks/Cole. p. 126. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0534373674" title="Special:BookSources/0534373674"><bdi>0534373674</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.place=Pacific+Grove%2C+CA&rft.pages=126&rft.edition=5th&rft.pub=Brooks%2FCole&rft.date=2000&rft.isbn=0534373674&rft.aulast=McMurry&rft.aufirst=John&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" 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="CITEREFWiberg1968" class="citation book cs1"><a href="/wiki/Kenneth_B._Wiberg" title="Kenneth B. Wiberg">Wiberg, K. B.</a> (1968). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9h0SBQAAQBAJ&pg=PA191">"Small Ring Bicyclo[<i>n</i>.<i>m</i>.0]alkanes"</a>. In Hart, H.; Karabatsos, G. J. (eds.). <i>Advances in Alicyclic Chemistry</i>. Vol. 2. <a href="/wiki/Academic_Press" title="Academic Press">Academic Press</a>. pp. 185–254. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781483224213" title="Special:BookSources/9781483224213"><bdi>9781483224213</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Small+Ring+Bicyclo%5Bn.m.0%5Dalkanes&rft.btitle=Advances+in+Alicyclic+Chemistry&rft.pages=185-254&rft.pub=Academic+Press&rft.date=1968&rft.isbn=9781483224213&rft.aulast=Wiberg&rft.aufirst=K.+B.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9h0SBQAAQBAJ%26pg%3DPA191&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" 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="CITEREFWibergLampmanCiulaConnor1965" class="citation journal cs1"><a href="/wiki/Kenneth_B._Wiberg" title="Kenneth B. Wiberg">Wiberg, K. B.</a>; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler, P.; Lavanish, J. (1965). "Bicyclo[1.1.0]butane". <i><a href="/wiki/Tetrahedron_(journal)" title="Tetrahedron (journal)">Tetrahedron</a></i>. <b>21</b> (10): 2749–2769. <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%2FS0040-4020%2801%2998361-9">10.1016/S0040-4020(01)98361-9</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Bicyclo%5B1.1.0%5Dbutane&rft.volume=21&rft.issue=10&rft.pages=2749-2769&rft.date=1965&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2801%2998361-9&rft.aulast=Wiberg&rft.aufirst=K.+B.&rft.au=Lampman%2C+G.+M.&rft.au=Ciula%2C+R.+P.&rft.au=Connor%2C+D.+S.&rft.au=Schertler%2C+P.&rft.au=Lavanish%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIrionNeuwirth2000" class="citation book cs1">Irion, Walther W.; Neuwirth, Otto S. (2000). "Oil Refining". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <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.a18_051">10.1002/14356007.a18_051</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-30673-0" title="Special:BookSources/3-527-30673-0"><bdi>3-527-30673-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Oil+Refining&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a18_051&rft.isbn=3-527-30673-0&rft.aulast=Irion&rft.aufirst=Walther+W.&rft.au=Neuwirth%2C+Otto+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACycloalkane" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</span> </li> </ol></div></div> <ul><li><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: (1995) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/C01497.html">Cycloalkanes</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C01497">10.1351/goldbook.C01497</a></li> <li>Organic Chemistry IUPAC Nomenclature. Rule A-23. Hydrogenated Compounds from Fused Polycyclic Hydrocarbons <a rel="nofollow" class="external free" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_73.htm">http://www.acdlabs.com/iupac/nomenclature/79/r79_73.htm</a></li> <li>Organic Chemistry IUPAC Nomenclature.Rule A-31. Bridged Hydrocarbons: Bicyclic Systems. <a rel="nofollow" class="external free" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_163.htm">http://www.acdlabs.com/iupac/nomenclature/79/r79_163.htm</a></li> <li>Organic Chemistry IUPAC Nomenclature.Rules A-41, A-42: Spiro Hydrocarbons <a rel="nofollow" class="external free" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_196.htm">http://www.acdlabs.com/iupac/nomenclature/79/r79_196.htm</a></li> <li>Organic Chemistry IUPAC Nomenclature.Rules A-51, A-52, A-53, A-54:Hydrocarbon Ring Assemblies <a rel="nofollow" class="external free" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_158.htm">http://www.acdlabs.com/iupac/nomenclature/79/r79_158.htm</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkane&action=edit&section=9" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.britannica.com/eb/article-79615/chemical-compound#615967.hook">"Cycloalkanes"</a> at the online <a href="/wiki/Encyclop%C3%A6dia_Britannica" title="Encyclopædia Britannica">Encyclopædia Britannica</a></li></ul> <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 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title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a class="mw-selflink selflink">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Cycloalkanes" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cycloalkanes" title="Template:Cycloalkanes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cycloalkanes" title="Template talk:Cycloalkanes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cycloalkanes" title="Special:EditPage/Template:Cycloalkanes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cycloalkanes" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Cycloalkanes</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li> <li><a href="/wiki/Cycloundecane" title="Cycloundecane">Cycloundecane</a></li> <li><a href="/wiki/Cyclododecane" title="Cyclododecane">Cyclododecane</a></li> <li><a href="/wiki/Cyclotridecane" title="Cyclotridecane">Cyclotridecane</a></li> <li><a href="/wiki/Cyclotetradecane" title="Cyclotetradecane">Cyclotetradecane</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q188862#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></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="https://d-nb.info/gnd/4148484-8">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85035091">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Cycloalcanes"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb121074472">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Cycloalcanes"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb121074472">BnF data</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=987007538313705171">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=Cycloalkane&oldid=1258768328">https://en.wikipedia.org/w/index.php?title=Cycloalkane&oldid=1258768328</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" 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