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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>In medicinal chemistry</span> </div> </a> <ul id="toc-In_medicinal_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkyl_cations,_anions,_and_radicals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Alkyl_cations,_anions,_and_radicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Alkyl cations, anions, and radicals</span> </div> </a> <ul id="toc-Alkyl_cations,_anions,_and_radicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Etymology" class="vector-toc-list-item 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class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Alkyl group</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 48 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-48" 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">48 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D9%8A%D9%84" title="ألكيل – Arabic" lang="ar" hreflang="ar" data-title="ألكيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%95%E0%A6%BE%E0%A6%87%E0%A6%B2_%E0%A6%AE%E0%A7%82%E0%A6%B2%E0%A6%95" title="অ্যালকাইল মূলক – Bangla" lang="bn" hreflang="bn" data-title="অ্যালকাইল মূলক" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D1%96%D0%BB%D1%8B" title="Алкілы – Belarusian" lang="be" hreflang="be" data-title="Алкілы" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%BA%D1%96%D0%BB%D1%8B" title="Алькілы – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Алькілы" 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%90%D0%BB%D0%BA%D0%B8%D0%BB" title="Алкил – Bulgarian" lang="bg" hreflang="bg" data-title="Алкил" 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/Alkil" title="Alkil – Bosnian" lang="bs" hreflang="bs" data-title="Alkil" 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/Grup_alquil" title="Grup alquil – Catalan" lang="ca" hreflang="ca" data-title="Grup alquil" 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/Alkyl" title="Alkyl – Czech" lang="cs" hreflang="cs" data-title="Alkyl" 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/Alkylgruppe" title="Alkylgruppe – German" lang="de" hreflang="de" data-title="Alkylgruppe" 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/Alk%C3%BC%C3%BClr%C3%BChm" title="Alküülrühm – Estonian" lang="et" hreflang="et" data-title="Alküülrühm" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CF%8D%CE%BB%CE%B9%CE%B1" title="Αλκύλια – Greek" lang="el" hreflang="el" data-title="Αλκύλια" 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/Alquilo" title="Alquilo – Spanish" lang="es" hreflang="es" data-title="Alquilo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Alkilo" title="Alkilo – Esperanto" lang="eo" hreflang="eo" data-title="Alkilo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Alkilo_talde" title="Alkilo talde – Basque" lang="eu" hreflang="eu" data-title="Alkilo talde" 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/%DA%AF%D8%B1%D9%88%D9%87_%D8%A2%D9%84%DA%A9%DB%8C%D9%84" title="گروه آلکیل – Persian" lang="fa" hreflang="fa" data-title="گروه آلکیل" 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/Alkyle" title="Alkyle – French" lang="fr" hreflang="fr" data-title="Alkyle" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Ailcil" title="Ailcil – Irish" lang="ga" hreflang="ga" data-title="Ailcil" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alquilo" title="Alquilo – Galician" lang="gl" hreflang="gl" data-title="Alquilo" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%ED%82%AC%EA%B8%B0" title="알킬기 – Korean" lang="ko" hreflang="ko" data-title="알킬기" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alkil" title="Alkil – Croatian" lang="hr" hreflang="hr" data-title="Alkil" 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/Alkil" title="Alkil – Indonesian" lang="id" hreflang="id" data-title="Alkil" 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/Alchile" title="Alchile – Italian" lang="it" hreflang="it" data-title="Alchile" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%99%D7%9C" title="אלקיל – Hebrew" lang="he" hreflang="he" data-title="אלקיל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alkil" title="Alkil – Hungarian" lang="hu" hreflang="hu" data-title="Alkil" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BB" title="Алкил – Macedonian" lang="mk" hreflang="mk" data-title="Алкил" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Kumpulan_alkil" title="Kumpulan alkil – Malay" lang="ms" hreflang="ms" data-title="Kumpulan alkil" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alkylgroep" title="Alkylgroep – Dutch" lang="nl" hreflang="nl" data-title="Alkylgroep" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%AD%E3%83%AB%E5%9F%BA" title="アルキル基 – Japanese" lang="ja" hreflang="ja" data-title="アルキル基" 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/Alkyl" title="Alkyl – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Alkyl" 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/Alkillar" title="Alkillar – Uzbek" lang="uz" hreflang="uz" data-title="Alkillar" 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-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%A7%DB%8C%D9%84" title="الکایل – Pashto" lang="ps" hreflang="ps" data-title="الکایل" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Grupa_alkilowa" title="Grupa alkilowa – Polish" lang="pl" hreflang="pl" data-title="Grupa alkilowa" 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/Alquila" title="Alquila – Portuguese" lang="pt" hreflang="pt" data-title="Alquila" 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/Alchil" title="Alchil – Romanian" lang="ro" hreflang="ro" data-title="Alchil" 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%90%D0%BB%D0%BA%D0%B8%D0%BB%D1%8B" title="Алкилы – Russian" lang="ru" hreflang="ru" data-title="Алкилы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alkyl" title="Alkyl – Simple English" lang="en-simple" hreflang="en-simple" data-title="Alkyl" 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/Alkylov%C3%A1_skupina" title="Alkylová skupina – Slovak" lang="sk" hreflang="sk" data-title="Alkylová skupina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%D8%A7%D9%84%DA%A9%DB%8C%D9%84" title="ئالکیل – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئالکیل" 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/Alkil" title="Alkil – Serbian" lang="sr" hreflang="sr" data-title="Alkil" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Alkyyli" title="Alkyyli – Finnish" lang="fi" hreflang="fi" data-title="Alkyyli" 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/Alkylgrupp" title="Alkylgrupp – Swedish" lang="sv" hreflang="sv" data-title="Alkylgrupp" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%88%E0%AE%B2%E0%AF%8D" title="அல்கைல் – Tamil" lang="ta" hreflang="ta" data-title="அல்கைல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/Alkyl" title="Alkyl – Kabyle" lang="kab" hreflang="kab" data-title="Alkyl" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alkil" title="Alkil – Turkish" lang="tr" hreflang="tr" data-title="Alkil" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D1%96%D0%BB%D1%8C%D0%BD%D1%96_%D0%B3%D1%80%D1%83%D0%BF%D0%B8" title="Алкільні групи – Ukrainian" lang="uk" hreflang="uk" data-title="Алкільні групи" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%A7%D8%A6%D9%84" title="الکائل – Urdu" lang="ur" hreflang="ur" data-title="الکائل" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Alkyl" title="Alkyl – Vietnamese" lang="vi" hreflang="vi" data-title="Alkyl" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%83%B7%E5%9F%BA" title="烷基 – Chinese" lang="zh" hreflang="zh" data-title="烷基" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q335268#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav 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(one hydrogen removed)</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Isopropyl_group.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Isopropyl_group.svg/100px-Isopropyl_group.svg.png" decoding="async" width="100" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Isopropyl_group.svg/150px-Isopropyl_group.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Isopropyl_group.svg/200px-Isopropyl_group.svg.png 2x" data-file-width="512" data-file-height="489" /></a><figcaption>Isopropyl group</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Methyl2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Methyl2.svg/100px-Methyl2.svg.png" decoding="async" width="100" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Methyl2.svg/150px-Methyl2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Methyl2.svg/200px-Methyl2.svg.png 2x" data-file-width="36" data-file-height="38" /></a><figcaption>Methyl group</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>alkyl group</b> is an <a href="/wiki/Alkane" title="Alkane">alkane</a> missing one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</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> The term <i>alkyl</i> is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>+1</sub></span>. A <b>cycloalkyl group</b> is derived from a <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkane</a> by removal of a hydrogen atom from a <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> and has the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>−1</sub></span>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Typically an alkyl is a part of a larger molecule. In <a href="/wiki/Structural_formula" title="Structural formula">structural formulae</a>, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>, with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span>.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Related_concepts">Related concepts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=1" title="Edit section: Related concepts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alkylation" title="Alkylation">Alkylation</a> is the addition of alkyl groups to molecules, often by alkylating agents such as <a href="/wiki/Haloalkane" title="Haloalkane">alkyl halides</a>. </p><p><a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">Alkylating antineoplastic agents</a> are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustards</a> are well-known alkylating agents, but they are not simple hydrocarbons. </p><p>In chemistry, alkyl is a group, a substituent, that is attached to other molecular fragments. For example, <a href="/wiki/Alkyl_lithium_reagent" class="mw-redirect" title="Alkyl lithium reagent">alkyl lithium reagents</a> have the empirical formula Li(alkyl), where alkyl = methyl, ethyl, etc. A <i>dialkyl</i> ether is an <a href="/wiki/Ether" title="Ether">ether</a> with two alkyl groups, e.g., diethyl ether <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O(CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>. </p> <div class="mw-heading mw-heading2"><h2 id="In_medicinal_chemistry">In medicinal chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=2" title="Edit section: In medicinal chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">medicinal chemistry</a>, the incorporation of alkyl chains into some <a href="/wiki/Chemical_compounds" class="mw-redirect" title="Chemical compounds">chemical compounds</a> increases their <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>. This strategy has been used to increase the antimicrobial activity of <a href="/wiki/Flavanone" title="Flavanone">flavanones</a> and <a href="/wiki/Chalcone" title="Chalcone">chalcones</a>.<sup id="cite_ref-medchem1_4-0" class="reference"><a href="#cite_note-medchem1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Alkyl_cations,_anions,_and_radicals"><span id="Alkyl_cations.2C_anions.2C_and_radicals"></span>Alkyl cations, anions, and radicals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=3" title="Edit section: Alkyl cations, anions, and radicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Usually, alkyl groups are attached to other atoms or groups of atoms. Free alkyls occur as neutral radicals, as anions, or as cations. The cations are called <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>. The anions are called <a href="/wiki/Carbanion" title="Carbanion">carbanions</a>. The neutral alkyl <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> have no special name. Such species are usually encountered only as transient intermediates. However, persistent alkyl radicals with <a href="/wiki/Half-life" title="Half-life">half-lives</a> "from seconds to years" have been prepared.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Typically alkyl cations are generated using <a href="/wiki/Superacid" title="Superacid">superacids</a> and alkyl anions are observed in the presence of strong bases. Alkyl radicals can be generated by a <a href="/wiki/Photochemical_reaction" class="mw-redirect" title="Photochemical reaction">photochemical reaction</a> or by <a href="/wiki/Homolytic_cleavage" class="mw-redirect" title="Homolytic cleavage">homolytic cleavage</a>.<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> Alkyls are commonly observed in <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>. Simple alkyls (especially <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>) are observed in the <a href="/wiki/Interstellar_space" class="mw-redirect" title="Interstellar space">interstellar space</a> as well. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=4" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkyl groups form <a href="/wiki/Homologous_series" title="Homologous series">homologous series</a>. The simplest series have the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>+1</sub></span>. Alkyls include <i><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a></i>, (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span>), <i><a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a></i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">5</sub></span>), <i><a href="/wiki/Propyl" class="mw-redirect" title="Propyl">propyl</a></i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">7</sub></span>), <i><a href="/wiki/Butyl" class="mw-redirect" title="Butyl">butyl</a></i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">9</sub></span>), <i><a href="/wiki/Pentyl" class="mw-redirect" title="Pentyl">pentyl</a></i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">11</sub></span>), and so on. Alkyl groups that contain one ring have the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>−1</sub></span>, e.g. cyclopropyl and cyclohexyl. The formula of alkyl radicals are the same as alkyl groups, except the free valence "<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−</span>" is replaced by the dot "•" and adding "radical" to the name of the alkyl group (e.g. <a href="/wiki/Methyl_radical" title="Methyl radical">methyl radical</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">•CH<sub class="template-chem2-sub">3</sub></span>). </p><p>The naming convention is taken from <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature</a>: </p> <table class="wikitable"> <tbody><tr> <th>Number of carbon atoms </th> <td>1 </td> <td>2 </td> <td>3 </td> <td>4 </td> <td>5 </td> <td>6 </td> <td>7 </td> <td>8 </td> <td>9 </td> <td>10 </td> <td>11 </td> <td>12 </td> <td>13 </td> <td>14 </td></tr> <tr> <th>Prefix </th> <td>meth- </td> <td>eth- </td> <td>prop- </td> <td>but- </td> <td>pent- </td> <td>hex- </td> <td>hept- </td> <td>oct- </td> <td>non- </td> <td>dec- </td> <td>undec- </td> <td>dodec- </td> <td>tridec- </td> <td>tetradec- </td></tr> <tr> <th>Group name </th> <td><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a> </td> <td><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a> </td> <td><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a> </td> <td><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a> </td> <td><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a> </td> <td>Hexyl </td> <td>Heptyl </td> <td>Octyl </td> <td>Nonyl </td> <td>Decyl </td> <td>Undecyl </td> <td>Dodecyl </td> <td>Tridecyl </td> <td>Tetradecyl </td></tr></tbody></table> <p><br /> The prefixes taken from IUPAC nomenclature are used to name branched chained structures by their <a href="/wiki/Substituent" title="Substituent">substituent</a> groups, for example <a href="/wiki/3-methylpentane" class="mw-redirect" title="3-methylpentane">3-methylpentane</a>: </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:3-MethylPentaneHighlighted.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/3-MethylPentaneHighlighted.svg/245px-3-MethylPentaneHighlighted.svg.png" decoding="async" width="245" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/3-MethylPentaneHighlighted.svg/368px-3-MethylPentaneHighlighted.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/3-MethylPentaneHighlighted.svg/490px-3-MethylPentaneHighlighted.svg.png 2x" data-file-width="245" data-file-height="150" /></a><figcaption></figcaption></figure> <p>The structure of <a href="/wiki/3-methylpentane" class="mw-redirect" title="3-methylpentane">3-methylpentane</a> is viewed as consisting of two parts. First, five atoms comprise the longest straight chain of <a href="/wiki/Carbon" title="Carbon">carbon</a> centers. The parent five-carbon compound is named <a href="/wiki/Pentane" title="Pentane">pentane</a> (highlighted blue). The methyl "substituent" or "group" is highlighted red. According to the usual rules of nomenclature, alkyl groups are included in the name of the molecule before the root, as in <a href="/wiki/Methylpentane" title="Methylpentane">methylpentane</a>. This name is, however, ambiguous, as the methyl branch could be on various carbon atoms. Thus, the name is 3-methylpentane to avoid ambiguity: The 3- is because the methyl is attached to the third of the five carbon atoms. </p><p>If there is more than one of the same alkyl group attached to a chain, then the prefixes are used on the alkyl groups to indicate multiples (i.e., di, tri, tetra, etc.) </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:2,3,3triMethylPentane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/2%2C3%2C3triMethylPentane.svg/235px-2%2C3%2C3triMethylPentane.svg.png" decoding="async" width="235" height="222" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/2%2C3%2C3triMethylPentane.svg/353px-2%2C3%2C3triMethylPentane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/2%2C3%2C3triMethylPentane.svg/470px-2%2C3%2C3triMethylPentane.svg.png 2x" data-file-width="235" data-file-height="222" /></a><figcaption></figcaption></figure> <p>This compound is known as <a href="/wiki/2,3,3-trimethylpentane" class="mw-redirect" title="2,3,3-trimethylpentane">2,3,3-trimethylpentane</a>. Here three identical alkyl groups attached to carbon atoms 2, 3, and 3. The numbers are included in the name to avoid ambiguity about the position of the groups, and "tri" indicates that there are three identical methyl groups. If one of the methyl groups attached to the third carbon atom were instead an ethyl group, then the name would be 3-ethyl-2,3-dimethylpentane. When there are different alkyl groups, they are listed in alphabetical order. </p><p>In addition, each position on an alkyl chain can be described according to how many other carbon atoms are attached to it. The terms <a href="/wiki/Primary_carbon" title="Primary carbon">primary</a>, <a href="/wiki/Secondary_carbon" title="Secondary carbon">secondary</a>, <a href="/wiki/Tertiary_carbon" title="Tertiary carbon">tertiary</a>, and <a href="/wiki/Quaternary_carbon" title="Quaternary carbon">quaternary</a> refer to a carbon attached to one, two, three, or four other carbons respectively. </p> <table class="wikitable"> <tbody><tr> <th><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub></span> </th> <th><a href="/wiki/Trivial_name" title="Trivial name">Trivial name</a> </th> <th>Symbol </th> <th><a href="/wiki/Structural_formula#Condensed_formulas" title="Structural formula">Condensed formula</a> </th> <th>IUPAC status </th> <th>Preferred IUPAC name </th> <th><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> </th></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">С<sub class="template-chem2-sub">1</sub></span> </td> <td><a href="/wiki/Methyl_group" title="Methyl group">methyl</a> </td> <td>Ме </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>methyl </td> <td> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">С<sub class="template-chem2-sub">2</sub></span> </td> <td><a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> </td> <td>Et </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>ethyl </td> <td> </td></tr> <tr> <td rowspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">С<sub class="template-chem2-sub">3</sub></span> </td> <td><a href="/wiki/Propyl" class="mw-redirect" title="Propyl">propyl</a>, <i>n</i>-propyl </td> <td>Pr, <sup><i>n</i></sup>Pr, <i>n</i>-Pr </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>propyl </td> <td> </td></tr> <tr> <td>isopropyl </td> <td><i>i</i>Pr, <i>i</i>-Pr,<sup><i>i</i></sup>Pr </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> </td> <td> </td> <td>2-propyl </td> <td> </td></tr> <tr> <td rowspan="4"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">С<sub class="template-chem2-sub">4</sub></span> </td> <td><i>n</i>-butyl </td> <td>Bu, <i>n</i>-Bu, <sup><i>n</i></sup>Bu </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>butyl </td> <td><span typeof="mw:File"><a href="/wiki/File:N-Butyl-Skeletal-SVG.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/N-Butyl-Skeletal-SVG.svg/100px-N-Butyl-Skeletal-SVG.svg.png" decoding="async" width="100" height="26" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/N-Butyl-Skeletal-SVG.svg/150px-N-Butyl-Skeletal-SVG.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/N-Butyl-Skeletal-SVG.svg/200px-N-Butyl-Skeletal-SVG.svg.png 2x" data-file-width="166" data-file-height="43" /></a></span> </td></tr> <tr> <td>isobutyl </td> <td><i>i</i>Bu, <i>i</i>-Bu, <sup><i>i</i></sup>Bu </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> </td> <td> </td> <td>2-methylpropyl </td> <td><span typeof="mw:File"><a href="/wiki/File:Isobutyl-Skeletal-SVG.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Isobutyl-Skeletal-SVG.svg/80px-Isobutyl-Skeletal-SVG.svg.png" decoding="async" width="80" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Isobutyl-Skeletal-SVG.svg/120px-Isobutyl-Skeletal-SVG.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Isobutyl-Skeletal-SVG.svg/160px-Isobutyl-Skeletal-SVG.svg.png 2x" data-file-width="129" data-file-height="75" /></a></span> </td></tr> <tr> <td><i>sec</i>-butyl </td> <td><i>s</i>Bu, <i>s</i>-Bu, <sup><i>s</i></sup>Bu </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH(−CH<sub class="template-chem2-sub">3</sub>)−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>2-butyl </td> <td><span typeof="mw:File"><a href="/wiki/File:Sec-Butyl-Skeletal-SVG.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Sec-Butyl-Skeletal-SVG.svg/80px-Sec-Butyl-Skeletal-SVG.svg.png" decoding="async" width="80" height="54" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Sec-Butyl-Skeletal-SVG.svg/120px-Sec-Butyl-Skeletal-SVG.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Sec-Butyl-Skeletal-SVG.svg/160px-Sec-Butyl-Skeletal-SVG.svg.png 2x" data-file-width="130" data-file-height="88" /></a></span> </td></tr> <tr> <td><i>tert</i>-butyl </td> <td><i>t</i>Bu, <i>t</i>-Bu, <sup><i>t</i></sup>Bu </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td><i>tert</i>-butyl </td> <td><span typeof="mw:File"><a href="/wiki/File:Tert-Butyl-Skeletal-SVG.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Tert-Butyl-Skeletal-SVG.svg/80px-Tert-Butyl-Skeletal-SVG.svg.png" decoding="async" width="80" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Tert-Butyl-Skeletal-SVG.svg/120px-Tert-Butyl-Skeletal-SVG.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Tert-Butyl-Skeletal-SVG.svg/160px-Tert-Butyl-Skeletal-SVG.svg.png 2x" data-file-width="96" data-file-height="90" /></a></span> </td></tr> <tr> <td rowspan="8"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">С<sub class="template-chem2-sub">5</sub></span> </td> <td><i>n</i>-pentyl, amyl </td> <td>Pe, Am, <i>n</i>Pe, <i>n</i>-Pe, <sup><i>n</i></sup>Pe, <sup><i>n</i></sup>Am </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>pentyl </td> <td> </td></tr> <tr> <td><i>tert</i>-pentyl </td> <td><i>t</i>Pe, <i>t</i>-Pe, <sup><i>t</i></sup>Pe </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td>No longer recommended </td> <td>2-methylbutan-2-yl (aka 1,1-dimethylpropyl) </td> <td> </td></tr> <tr> <td>neopentyl </td> <td> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−C(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span> </td> <td>No longer recommended </td> <td>2,2-dimethylpropyl </td> <td> </td></tr> <tr> <td>isopentyl, isoamyl </td> <td> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> </td> <td>No longer recommended </td> <td>3-methylbutyl </td> <td> </td></tr> <tr> <td><i>sec</i>-pentyl </td> <td><i>s</i>Pe, <i>s</i>-Pe, <sup><i>s</i></sup>Pe </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH(−CH<sub class="template-chem2-sub">3</sub>)−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>pentan-2-yl(or (1-Methylbutyl)) </td> <td> </td></tr> <tr> <td>3-pentyl </td> <td> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH(−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> </td> <td> </td> <td>pentan-3-yl (also known as (1-Ethylpropyl)) </td> <td> </td></tr> <tr> <td><i>sec</i>-isopentyl, <i>sec</i>-isoamyl, siamyl </td> <td>Sia </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH(−CH<sub class="template-chem2-sub">3</sub>)−CH(−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> </td> <td> </td> <td>3-methylbutan-2-yl (or (1,2-Dimethylpropyl)) </td> <td> </td></tr> <tr> <td>active pentyl </td> <td> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−CH(−CH<sub class="template-chem2-sub">3</sub>)−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">3</sub></span> </td> <td> </td> <td>2-methylbutyl </td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Etymology">Etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=5" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first named alkyl radical was ethyl, named so by <a href="/wiki/Liebig" class="mw-redirect" title="Liebig">Liebig</a> in 1833 from the German word "Äther" (which in turn had been derived from the Greek word "<a href="/wiki/Aether_(classical_element)" title="Aether (classical element)">aither</a>" meaning "air", for the substance now known as <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>) and the Greek word ύλη (<a href="/wiki/Hyle" class="mw-redirect" title="Hyle">hyle</a>), meaning "matter".<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> This was followed by methyl (<a href="/wiki/Jean-Baptiste_Dumas" title="Jean-Baptiste Dumas">Dumas</a> and <a href="/wiki/Eug%C3%A8ne-Melchior_P%C3%A9ligot" title="Eugène-Melchior Péligot">Peligot</a> in 1834, meaning "spirit of wood"<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>) and amyl (<a href="/wiki/Auguste_Andr%C3%A9_Thomas_Cahours" title="Auguste André Thomas Cahours">Auguste Cahours</a> in 1840<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>). The word alkyl was introduced by <a href="/wiki/Johannes_Wislicenus" title="Johannes Wislicenus">Johannes Wislicenus</a> in or before 1882, based on the German word "Alkoholradikale" and then-common suffix -yl.<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><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkyl_group&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/alkyl_group" class="extiw" title="wiktionary:Special:Search/alkyl group">alkyl group</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li><a href="/wiki/Alkane" title="Alkane">Alkane</a></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a></li> <li><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbon</a></li> <li><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature of organic chemistry</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=Alkyl_group&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). 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Springer. p. 62. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-27415-2" title="Special:BookSources/978-3-642-27415-2"><bdi>978-3-642-27415-2</bdi></a>. <q>Ethyl radicals (named by Liebig in 1833 from the Greek and German word "aether" plus Greek "hyle"<span class="cs1-kern-right"></span></q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+the+Molecular+World%3A+A+Nineteenth-Century+Science+Fantasy&rft.pages=62&rft.pub=Springer&rft.date=2012&rft.isbn=978-3-642-27415-2&rft.aulast=Rocke&rft.aufirst=Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkyl+group" 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="CITEREFRocke2012" class="citation book cs1">Rocke, Alan (2012). <i>From the Molecular World: A Nineteenth-Century Science Fantasy</i>. Springer. p. 62. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-27415-2" title="Special:BookSources/978-3-642-27415-2"><bdi>978-3-642-27415-2</bdi></a>. <q>The methyl radical ... named from Greek roots, by Dumas and Peligot in 1834: methyl = methy + hyle ("spirit" + "wood")</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+the+Molecular+World%3A+A+Nineteenth-Century+Science+Fantasy&rft.pages=62&rft.pub=Springer&rft.date=2012&rft.isbn=978-3-642-27415-2&rft.aulast=Rocke&rft.aufirst=Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkyl+group" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRocke2012" class="citation book cs1">Rocke, Alan (2012). <i>From the Molecular World: A Nineteenth-Century Science Fantasy</i>. Springer. p. 62. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-27415-2" title="Special:BookSources/978-3-642-27415-2"><bdi>978-3-642-27415-2</bdi></a>. <q>Amyl radicals ("amilène" was coined by Auguste Cahours in 1840, to designate a substance from potato starch after fermentation and distillation</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+the+Molecular+World%3A+A+Nineteenth-Century+Science+Fantasy&rft.pages=62&rft.pub=Springer&rft.date=2012&rft.isbn=978-3-642-27415-2&rft.aulast=Rocke&rft.aufirst=Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkyl+group" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRocke2012" class="citation book cs1">Rocke, Alan (2012). <i>From the Molecular World: A Nineteenth-Century Science Fantasy</i>. Springer. p. 62. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-27415-2" title="Special:BookSources/978-3-642-27415-2"><bdi>978-3-642-27415-2</bdi></a>. <q><span class="cs1-kern-left"></span>"Alkyl" was coined without fanfare by Johannes Wislicenus, professor at Würzburg; an early use (perhaps not the first) is in his 1882 article [22, 244]. The word was derived from the first three letters of "Alkoholradicale" combined with the suffix -yl; it was (and is) a generic term for any of those radicals who bear the "first names" methyl, ethyl, propyl, butyl, amyl, etc.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+the+Molecular+World%3A+A+Nineteenth-Century+Science+Fantasy&rft.pages=62&rft.pub=Springer&rft.date=2012&rft.isbn=978-3-642-27415-2&rft.aulast=Rocke&rft.aufirst=Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkyl+group" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWisclicenus1882" class="citation journal cs1">Wisclicenus, Johannes (1882). "Ueber die Schätzung von Haftenenergien der Halogene und des Natriums an organischen Resten". <i>Ann. Chem</i>. <b>212</b>: 239–250. <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%2Fjlac.18822120107">10.1002/jlac.18822120107</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ann.+Chem.&rft.atitle=Ueber+die+Sch%C3%A4tzung+von+Haftenenergien+der+Halogene+und+des+Natriums+an+organischen+Resten&rft.volume=212&rft.pages=239-250&rft.date=1882&rft_id=info%3Adoi%2F10.1002%2Fjlac.18822120107&rft.aulast=Wisclicenus&rft.aufirst=Johannes&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkyl+group" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist 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rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></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/Q335268#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/4346214-5">Germany</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=Alkyl_group&oldid=1238646988">https://en.wikipedia.org/w/index.php?title=Alkyl_group&oldid=1238646988</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Alkyl_groups" title="Category:Alkyl groups">Alkyl groups</a></li><li><a href="/wiki/Category:Substituents" title="Category:Substituents">Substituents</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden 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