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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Stereochemistry of ketonization</span> </div> </a> <ul id="toc-Stereochemistry_of_ketonization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enediols" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Enediols"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Enediols</span> </div> </a> <ul id="toc-Enediols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phenols" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phenols"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Phenols</span> </div> </a> <ul id="toc-Phenols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Reactivity</span> </div> </a> <button aria-controls="toc-Reactivity-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 Reactivity subsection</span> </button> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> <li id="toc-Addition_of_electrophiles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_of_electrophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Addition of electrophiles</span> </div> </a> <ul id="toc-Addition_of_electrophiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deprotonation:_enolates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deprotonation:_enolates"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Deprotonation: enolates</span> </div> </a> <ul id="toc-Deprotonation:_enolates-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Stable_enols" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Stable_enols"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Stable enols</span> </div> </a> <ul id="toc-Stable_enols-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">8</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">9</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">10</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">Enol</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 37 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-37" 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">37 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%A5%D9%8A%D9%86%D9%88%D9%84" title="إينول – Arabic" lang="ar" hreflang="ar" data-title="إينول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D0%BD%D0%BE%D0%BB" title="Енол – Bulgarian" lang="bg" hreflang="bg" data-title="Енол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Enol" title="Enol – Catalan" lang="ca" hreflang="ca" data-title="Enol" 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/Enol" title="Enol – Czech" lang="cs" hreflang="cs" data-title="Enol" 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/Enole" title="Enole – German" lang="de" hreflang="de" data-title="Enole" 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/Enoolid" title="Enoolid – Estonian" lang="et" hreflang="et" data-title="Enoolid" 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%95%CE%BD%CF%8C%CE%BB%CE%B5%CF%82" title="Ενόλες – Greek" lang="el" hreflang="el" data-title="Ενόλες" 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/Enol" title="Enol – Spanish" lang="es" hreflang="es" data-title="Enol" 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/Enol" title="Enol – Basque" lang="eu" hreflang="eu" data-title="Enol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%86%D9%88%D9%84" title="انول – Persian" lang="fa" hreflang="fa" data-title="انول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89nol" title="Énol – French" lang="fr" hreflang="fr" data-title="Énol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Enol" title="Enol – Galician" lang="gl" hreflang="gl" data-title="Enol" 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%97%94%EC%98%AC" title="엔올 – Korean" lang="ko" hreflang="ko" data-title="엔올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B5%D5%B6%D5%B8%D5%AC%D5%B6%D5%A5%D6%80" title="Ենոլներ – Armenian" lang="hy" hreflang="hy" data-title="Ենոլներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Enol" title="Enol – Indonesian" lang="id" hreflang="id" data-title="Enol" 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/Enoli" title="Enoli – Italian" lang="it" hreflang="it" data-title="Enoli" 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%A0%D7%95%D7%9C" title="אנול – Hebrew" lang="he" hreflang="he" data-title="אנול" 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/Enolok" title="Enolok – Hungarian" lang="hu" hreflang="hu" data-title="Enolok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%95%D0%BD%D0%BE%D0%BB" title="Енол – Macedonian" lang="mk" hreflang="mk" data-title="Енол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Enol" title="Enol – Dutch" lang="nl" hreflang="nl" data-title="Enol" 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%A8%E3%83%8E%E3%83%BC%E3%83%AB" title="エノール – Japanese" lang="ja" hreflang="ja" data-title="エノール" 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/Enol" title="Enol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Enol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Enol" title="Enol – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Enol" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Enole" title="Enole – Polish" lang="pl" hreflang="pl" data-title="Enole" 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/Enol" title="Enol – Portuguese" lang="pt" hreflang="pt" data-title="Enol" 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/Enol" title="Enol – Romanian" lang="ro" hreflang="ro" data-title="Enol" 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%95%D0%BD%D0%BE%D0%BB%D1%8B" title="Енолы – Russian" lang="ru" hreflang="ru" data-title="Енолы" 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/Enol" title="Enol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Enol" 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/Enol" title="Enol – Slovak" lang="sk" hreflang="sk" data-title="Enol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Enol" title="Enol – Serbian" lang="sr" hreflang="sr" data-title="Enol" 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/Enol" title="Enol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Enol" 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/Enolit" title="Enolit – Finnish" lang="fi" hreflang="fi" data-title="Enolit" 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/Enol" title="Enol – Swedish" lang="sv" hreflang="sv" data-title="Enol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Enol" title="Enol – Turkish" lang="tr" hreflang="tr" data-title="Enol" 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%95%D0%BD%D0%BE%D0%BB%D0%B8" title="Еноли – Ukrainian" lang="uk" hreflang="uk" data-title="Еноли" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Enol" title="Enol – Vietnamese" lang="vi" hreflang="vi" data-title="Enol" 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%AF%E9%86%87" title="烯醇 – Chinese" lang="zh" hreflang="zh" data-title="烯醇" 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/Q408053#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul 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.trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:254px;max-width:254px"><div class="trow"><div class="theader" style="text-align:center">Examples of keto-enol <a href="/wiki/Tautomerism" class="mw-redirect" title="Tautomerism">tautomerism</a></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Enol.png" class="mw-file-description"><img alt="TBD" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Enol.png/250px-Enol.png" decoding="async" width="250" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Enol.png/375px-Enol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/Enol.png/500px-Enol.png 2x" data-file-width="1478" data-file-height="294" /></a></span></div><div class="thumbcaption text-align-left">Ketone <a href="/wiki/Tautomerization" class="mw-redirect" title="Tautomerization">tautomerization</a>, keto-form at left, enol at right. Ex. is <a href="/wiki/3-pentanone" class="mw-redirect" title="3-pentanone">3-pentanone</a>, a less stabilized enol.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup></div></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Enolate_Resonance.svg" class="mw-file-description"><img alt="TBD" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Enolate_Resonance.svg/250px-Enolate_Resonance.svg.png" decoding="async" width="250" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Enolate_Resonance.svg/375px-Enolate_Resonance.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Enolate_Resonance.svg/500px-Enolate_Resonance.svg.png 2x" data-file-width="239" data-file-height="83" /></a></span></div><div class="thumbcaption text-align-left">Enolate <a href="/wiki/Resonance_structures" class="mw-redirect" title="Resonance structures">resonance structures</a>, schematic representation of forms (see text regarding <a href="/wiki/Molecular_orbital" title="Molecular orbital">molecular orbitals</a>); <a href="/wiki/Carbanion" title="Carbanion">carbanion</a> form at left, <a href="/wiki/Enolate" title="Enolate">enolate</a> at right; Ex. is <a href="/wiki/2-butanone" class="mw-redirect" title="2-butanone">2-butanone</a>, also a less stabilized enol.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup></div></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:AcacH.svg" class="mw-file-description"><img alt="TBD" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/250px-AcacH.svg.png" decoding="async" width="250" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/375px-AcacH.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/500px-AcacH.svg.png 2x" data-file-width="512" data-file-height="123" /></a></span></div><div class="thumbcaption text-align-left">Ketone <a href="/wiki/Tautomerization" class="mw-redirect" title="Tautomerization">tautomerization</a>, enol-form at left, keto at right. Ex. is <a href="/wiki/2,4-pentanedione" class="mw-redirect" title="2,4-pentanedione">2,4-pentanedione</a>, a <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bond</a> (---) stabilized enol.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup></div></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Tartronaldehyde.svg" class="mw-file-description"><img alt="TBD" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Tartronaldehyde.svg/250px-Tartronaldehyde.svg.png" decoding="async" width="250" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Tartronaldehyde.svg/375px-Tartronaldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Tartronaldehyde.svg/500px-Tartronaldehyde.svg.png 2x" data-file-width="769" data-file-height="140" /></a></span></div><div class="thumbcaption text-align-left">Aldehyde <a href="/wiki/Tautomerization" class="mw-redirect" title="Tautomerization">tautomerization</a>, enol-form at left, "keto" at right; Ex. is <a href="/wiki/Tartronaldehyde" class="mw-redirect" title="Tartronaldehyde">tartronaldehyde</a> (reductone), an <a href="/wiki/Enediol" class="mw-redirect" title="Enediol">enediol</a>-type of enol.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup></div></div></div></div></div> </div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>enols</b> are a type of <a href="/wiki/Functional_group" title="Functional group">Functional group</a> or <a href="/wiki/Chemical_intermediate" class="mw-redirect" title="Chemical intermediate">intermediate</a> in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> containing a group with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C=C(OH)</span> (R = many substituents). The term <i>enol</i> is an abbreviation of <i>alkenol</i>, a <a href="/wiki/Portmanteau" class="mw-redirect" title="Portmanteau">portmanteau</a> deriving from "-ene"/"alkene" and the "-ol". Many kinds of enols are known.<sup id="cite_ref-March_1-0" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><b>Keto–enol tautomerism</b> refers to a <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">chemical equilibrium</a> between a "keto" form (a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a>, named for the common <a href="/wiki/Ketone" title="Ketone">ketone</a> case) and an enol. The interconversion of the two forms involves the transfer of an alpha hydrogen atom and the reorganisation of bonding <a href="/wiki/Electron" title="Electron">electrons</a>. The keto and enol forms are <a href="/wiki/Tautomerism" class="mw-redirect" title="Tautomerism">tautomers</a> of each other.<sup id="cite_ref-Clayden-2012_2-0" class="reference"><a href="#cite_note-Clayden-2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Enolization">Enolization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=1" title="Edit section: Enolization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Organic_compound" title="Organic compound">Organic</a> <a href="/wiki/Ester" title="Ester">esters</a>, <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">ketones</a>, and <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a> with an <a href="/wiki/%CE%91-hydrogen" class="mw-redirect" title="Α-hydrogen">α-hydrogen</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> bond adjacent to the <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a>) often form enols. The reaction involves migration of a proton (<span style="color: red;">H</span>) from carbon to oxygen:<sup id="cite_ref-March_1-1" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RC(=O)C<span style="color: red;">H</span>R′R′′ ⇌ RC(O<span style="color: red;">H</span>)=CR′R′′</span></dd></dl> <p>In the case of ketones, the conversion is called a keto-enol tautomerism, although this name is often more generally applied to all such tautomerizations. Usually the equilibrium constant is so small that the enol is undetectable spectroscopically. </p><p>In some compounds with two (or more) carbonyls, the enol form becomes dominant. The behavior of <a href="/wiki/2,4-pentanedione" class="mw-redirect" title="2,4-pentanedione">2,4-pentanedione</a> illustrates this effect:<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> <dl><dd><figure class="mw-halign-left skin-invert-image" typeof="mw:File"><a href="/wiki/File:AcacH.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/200px-AcacH.svg.png" decoding="async" width="200" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/300px-AcacH.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/400px-AcacH.svg.png 2x" data-file-width="512" data-file-height="123" /></a><figcaption></figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <table class="wikitable"> <caption>Selected enolization constants<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> </caption> <tbody><tr> <th>carbonyl </th> <th>enol </th> <th>K<sub>enolization</sub> </th></tr> <tr> <td><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CHO</span> </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>=CHOH</span> </td> <td>5.8<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999300000000000000♠"></span>−7</span></sup> </td></tr> <tr> <td><a href="/wiki/Acetone" title="Acetone">Acetone</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">3</sub></span> </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>C(OH)=CH<sub class="template-chem2-sub">2</sub></span> </td> <td>5.12<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999300000000000000♠"></span>−7</span></sup> </td></tr> <tr> <td><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> </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(OH)OCH<sub class="template-chem2-sub">3</sub></span> </td> <td>4<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2998800000000000000♠"></span>−20</span></sup> </td></tr> <tr> <td><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>C(O)CH<sub class="template-chem2-sub">3</sub></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>C(OH)=CH<sub class="template-chem2-sub">2</sub></span> </td> <td>1<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999200000000000000♠"></span>−8</span></sup> </td></tr> <tr> <td><a href="/wiki/Acetylacetone" title="Acetylacetone">Acetylacetone</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CH<sub class="template-chem2-sub">3</sub></span> </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>C(O)CH=C(OH)CH<sub class="template-chem2-sub">3</sub></span> </td> <td>0.27 </td></tr> <tr> <td><a href="/wiki/1,1,1-Trifluoroacetylacetone" title="1,1,1-Trifluoroacetylacetone">Trifluoroacetylacetone</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CF<sub class="template-chem2-sub">3</sub></span> </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>C(O)CH=C(OH)CF<sub class="template-chem2-sub">3</sub></span> </td> <td>32 </td></tr> <tr> <td><a href="/wiki/Hexafluoroacetylacetone" title="Hexafluoroacetylacetone">Hexafluoroacetylacetone</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CF<sub class="template-chem2-sub">3</sub></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>C(O)CH=C(OH)CF<sub class="template-chem2-sub">3</sub></span> </td> <td>~10<sup>4</sup> </td></tr> <tr> <td>Cyclohexa-2,4-dienone </td> <td><a href="/wiki/Phenol" title="Phenol">Phenol</a><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH</span> </td> <td>>10<sup>12</sup> </td></tr></tbody></table> <p>Enols are derivatives of <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a>, with a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=C−OH</span> connectivity. Deprotonation of organic carbonyls gives the <a href="/wiki/Enolate_anion" class="mw-redirect" title="Enolate anion">enolate anion</a>, which are a strong <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. A classic example for favoring the keto form can be seen in the equilibrium between <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a> and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> (K = [enol]/[keto] ≈ 3<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999300000000000000♠"></span>−7</span></sup>). In <a href="/wiki/Diketone#1,3-Diketones" class="mw-redirect" title="Diketone">1,3-diketones</a>, such as <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a> (2,4-pentanedione), the enol form is favored. </p><p>The acid-catalyzed conversion of an enol to the keto form proceeds by proton transfer from O to carbon. The process does not occur intramolecularly, but requires participation of solvent or other mediators. </p> <div class="mw-heading mw-heading2"><h2 id="Stereochemistry_of_ketonization">Stereochemistry of ketonization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=2" title="Edit section: Stereochemistry of ketonization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If R<sup>1</sup> and R<sup>2</sup> (note equation at top of page) are different substituents, there is a new stereocenter formed at the alpha position when an enol converts to its keto form. Depending on the nature of the three R groups, the resulting products in this situation would be <a href="/wiki/Diastereomer" title="Diastereomer">diastereomers</a> or <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Enediols">Enediols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=3" title="Edit section: Enediols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Enediols are alkenes with a hydroxyl group on each carbon of the C=C double bond. Normally such compounds are disfavored components in equilibria with <a href="/wiki/Acyloin" title="Acyloin">acyloins</a>. One special case is <a href="/wiki/Catechol" title="Catechol">catechol</a>, where the C=C subunit is part of an aromatic ring. In some other cases however, enediols are stabilized by flanking carbonyl groups. These stabilized enediols are called <a href="/wiki/Reductone" title="Reductone">reductones</a>. Such species are important in glycochemistry, e.g., the <a href="/wiki/Lobry_de_Bruyn-van_Ekenstein_transformation" class="mw-redirect" title="Lobry de Bruyn-van Ekenstein transformation">Lobry de Bruyn-van Ekenstein transformation</a>.<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> </p> <dl><dd><figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Keto-Endiol-Tautomerie.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Keto-Endiol-Tautomerie.svg/350px-Keto-Endiol-Tautomerie.svg.png" decoding="async" width="350" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Keto-Endiol-Tautomerie.svg/525px-Keto-Endiol-Tautomerie.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Keto-Endiol-Tautomerie.svg/700px-Keto-Endiol-Tautomerie.svg.png 2x" data-file-width="779" data-file-height="175" /></a><figcaption><b>Keto-enediol tautomerizations.</b> Enediol in the center; <a href="/wiki/Acyloin" title="Acyloin">acyloin</a> isomers at left and right. Ex. is <a href="/wiki/Hydroxyacetone" title="Hydroxyacetone">hydroxyacetone</a>, shown at right.</figcaption></figure></dd></dl> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Ascorbic_acidity3.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Ascorbic_acidity3.png/350px-Ascorbic_acidity3.png" decoding="async" width="350" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Ascorbic_acidity3.png/525px-Ascorbic_acidity3.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Ascorbic_acidity3.png/700px-Ascorbic_acidity3.png 2x" data-file-width="3317" data-file-height="761" /></a><figcaption>Conversion of <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> (vitamin C) to an enolate. Enediol at left, enolate at right, showing movement of electron pairs resulting in deprotonation of the stable parent enediol. A distinct, more complex chemical system, exhibiting the characteristic of <a href="/wiki/Vinylogy" title="Vinylogy">vinylogy</a>.</figcaption></figure> <p><a href="/wiki/Ribulose-1,5-bisphosphate" class="mw-redirect" title="Ribulose-1,5-bisphosphate">Ribulose-1,5-bisphosphate</a> is a key substrate in the <a href="/wiki/Calvin_cycle" title="Calvin cycle">Calvin cycle</a> of <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. In the Calvin cycle, the ribulose equilibrates with the enediol, which then binds <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. The same enediol is also susceptible to attack by oxygen (O<sub>2</sub>) in the (undesirable) process called <a href="/wiki/Photorespiration" title="Photorespiration">photorespiration</a>. </p> <figure class="mw-default-size mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:EnediolPhotoResp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/EnediolPhotoResp.svg/220px-EnediolPhotoResp.svg.png" decoding="async" width="220" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/EnediolPhotoResp.svg/330px-EnediolPhotoResp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/EnediolPhotoResp.svg/440px-EnediolPhotoResp.svg.png 2x" data-file-width="271" data-file-height="143" /></a><figcaption>Keto-enediol equilibrium for <a href="/wiki/Ribulose-1,5-bisphosphate" class="mw-redirect" title="Ribulose-1,5-bisphosphate">ribulose-1,5-bisphosphate</a>.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Phenols">Phenols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=4" title="Edit section: Phenols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Phenol" title="Phenol">Phenols</a> represent a kind of enol. For some phenols and related compounds, the keto tautomer plays an important role. Many of the reactions of <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a> involve the keto tautomer, for example. Naphthalene-1,4-diol exists in observable equilibrium with the diketone tetrahydronaphthalene-1,4-dione.<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> <dl><dd><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tetrahydronaphthalenedione.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/220px-Tetrahydronaphthalenedione.png" decoding="async" width="220" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/330px-Tetrahydronaphthalenedione.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/440px-Tetrahydronaphthalenedione.png 2x" data-file-width="1480" data-file-height="692" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=5" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Keto–enol tautomerism is important in several areas of <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p><p>The high phosphate-transfer potential of <a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">phosphoenolpyruvate</a> results from the fact that the phosphorylated compound is "trapped" in the less thermodynamically favorable enol form, whereas after dephosphorylation it can assume the keto form.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p><p>The <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Enolase" title="Enolase">enolase</a> catalyzes the dehydration of <a href="/wiki/2-phosphoglyceric_acid" class="mw-redirect" title="2-phosphoglyceric acid">2-phosphoglyceric acid</a> to the enol phosphate ester. Metabolism of PEP to <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> by <a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">pyruvate kinase</a> (PK) generates <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) via <a href="/wiki/Substrate-level_phosphorylation" title="Substrate-level phosphorylation">substrate-level phosphorylation</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <table style="background: white; text-align:center;"> <tbody><tr> <td rowspan="5"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:2-phospho-D-glycerate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/2/28/2-phospho-D-glycerate_wpmp.png" decoding="async" width="125" height="98" class="mw-file-element" data-file-width="125" data-file-height="98" /></a></span> </td> <td colspan="2" style="width:75px"> </td> <td rowspan="5"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Phosphoenolpyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/a/ad/Phosphoenolpyruvate_wpmp.png" decoding="async" width="78" height="126" class="mw-file-element" data-file-width="78" data-file-height="126" /></a></span> </td> <td colspan="2" style="width:75px"> </td> <td rowspan="5"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Pyruvate_wpmp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/c/c7/Pyruvate_wpmp.png" decoding="async" width="63" height="62" class="mw-file-element" data-file-width="63" data-file-height="62" /></a></span> </td></tr> <tr> <td> </td> <td>H<sub>2</sub>O </td> <td><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a> </td> <td><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> </td></tr> <tr> <td colspan="2" style="width:75px"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/75px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/113px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/150px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td> <td colspan="2" style="width:75px"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg/75px-Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg/113px-Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg/150px-Biochem_reaction_arrow_reversible_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span> </td></tr> <tr> <td> </td> <td>H<sub>2</sub>O </td> <td> </td> <td> </td></tr> <tr> <td colspan="2" style="width:75px"> </td> <td colspan="2" style="width:75px"> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=6" title="Edit section: Reactivity"><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/Carbonyl_%CE%B1-substitution_reactions" class="mw-redirect" title="Carbonyl α-substitution reactions">Carbonyl α-substitution reactions</a></div> <div class="mw-heading mw-heading3"><h3 id="Addition_of_electrophiles">Addition of electrophiles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=7" title="Edit section: Addition of electrophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The terminus of the double bond in enols is <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic</a>. Its reactions with <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> organic compounds is important in <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a> as well as <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthetic organic chemistry</a>. In the former area, the fixation of carbon dioxide involves addition of CO<sub>2</sub> to an enol.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Deprotonation:_enolates">Deprotonation: enolates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=8" title="Edit section: Deprotonation: enolates"><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/Enolate" title="Enolate">enolate</a></div> <p>Deprotonation of enolizable ketones, aldehydes, and esters gives <a href="/wiki/Enolate" title="Enolate">enolates</a>.<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><sup id="cite_ref-enolate_9-0" class="reference"><a href="#cite_note-enolate-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Enolates can be trapped by the addition of electrophiles at oxygen. Silylation gives <a href="/wiki/Silyl_enol_ether" title="Silyl enol ether">silyl enol ether</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> Acylation gives esters such as <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a>.<sup id="cite_ref-Ullmann_11-0" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Stable_enols">Stable enols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enol&action=edit&section=9" title="Edit section: Stable enols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, enols are less stable than their keto equivalents because of the favorability of the C=O double bond over C=C double bond. However, enols can be stabilized kinetically or thermodynamically.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p><p>Some enols are sufficiently stabilized kinetically so that they can be characterized.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Hindrance.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Hindrance.png/220px-Hindrance.png" decoding="async" width="220" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Hindrance.png/330px-Hindrance.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Hindrance.png/440px-Hindrance.png 2x" data-file-width="887" data-file-height="620" /></a><figcaption>Diaryl-substitution stabilizes some enols.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Delocalization can stabilize the enol tautomer. Thus, very stable enols are <a href="/wiki/Phenol" title="Phenol">phenols</a>.<sup id="cite_ref-:0_13-0" class="reference"><a href="#cite_note-:0-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Another stabilizing factor in 1,3-dicarbonyls is intramolecular hydrogen bonding.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Both of these factors influence the enol-dione equilibrium in acetylacetone. </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=Enol&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkenal" class="mw-redirect" title="Alkenal">Alkenal</a></li> <li><a href="/wiki/Enolase" title="Enolase">Enolase</a></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynol" class="mw-redirect" title="Ynol">Ynol</a></li> <li><a href="/wiki/Geminal_diol" title="Geminal diol">Geminal diol</a>, another form of ketones and aldehydes in water solutions</li> <li><a href="/wiki/Regioselectivity" title="Regioselectivity">Regioselectivity</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=Enol&action=edit&section=11" 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-March-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSmith_MB,_March_J2001" class="citation book cs1">Smith MB, March J (2001). <i>Advanced Organic Chemistry</i> (5th ed.). New York: <a href="/wiki/Wiley_Interscience" class="mw-redirect" title="Wiley Interscience">Wiley Interscience</a>. pp. 1218–1223. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-58589-0" title="Special:BookSources/0-471-58589-0"><bdi>0-471-58589-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry&rft.place=New+York&rft.pages=1218-1223&rft.edition=5th&rft.pub=Wiley+Interscience&rft.date=2001&rft.isbn=0-471-58589-0&rft.au=Smith+MB%2C+March+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" class="Z3988"></span></span> </li> <li id="cite_note-Clayden-2012-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Clayden-2012_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1">Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). <i>Organic chemistry</i> (2nd ed.). 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Peter; Povar, Igor (2013). "Equilibrium constants for enolization in solution by computation alone". <i>Journal of Physical Organic Chemistry</i>. <b>26</b> (12): 1077–1083. <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%2Fpoc.3168">10.1002/poc.3168</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Physical+Organic+Chemistry&rft.atitle=Equilibrium+constants+for+enolization+in+solution+by+computation+alone&rft.volume=26&rft.issue=12&rft.pages=1077-1083&rft.date=2013&rft_id=info%3Adoi%2F10.1002%2Fpoc.3168&rft.aulast=Guthrie&rft.aufirst=J.+Peter&rft.au=Povar%2C+Igor&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchank,_Kurt1972" class="citation journal cs1">Schank, Kurt (1972). "Reductones". <i>Synthesis</i>. <b>1972</b> (4): 176–90. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-1972-21845">10.1055/s-1972-21845</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:260331550">260331550</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synthesis&rft.atitle=Reductones&rft.volume=1972&rft.issue=4&rft.pages=176-90&rft.date=1972&rft_id=info%3Adoi%2F10.1055%2Fs-1972-21845&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A260331550%23id-name%3DS2CID&rft.au=Schank%2C+Kurt&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" 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="CITEREFKündigEnríquez_GarcíaLombergetBernardinelli2006" class="citation journal cs1">Kündig, E. Peter; Enríquez García, Alvaro; Lomberget, Thierry; Bernardinelli, Gérald (2006). "Rediscovery, Isolation, and Asymmetric Reduction of 1,2,3,4-Tetrahydronaphthalene-1,4-dione and Studies of Its [Cr(CO)3] Complex". <i>Angewandte Chemie International Edition</i>. <b>45</b> (1): 98–101. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200502588">10.1002/anie.200502588</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16304647">16304647</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Rediscovery%2C+Isolation%2C+and+Asymmetric+Reduction+of+1%2C2%2C3%2C4-Tetrahydronaphthalene-1%2C4-dione+and+Studies+of+Its+%5BCr%28CO%293%5D+Complex&rft.volume=45&rft.issue=1&rft.pages=98-101&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2Fanie.200502588&rft_id=info%3Apmid%2F16304647&rft.aulast=K%C3%BCndig&rft.aufirst=E.+Peter&rft.au=Enr%C3%ADquez+Garc%C3%ADa%2C+Alvaro&rft.au=Lomberget%2C+Thierry&rft.au=Bernardinelli%2C+G%C3%A9rald&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" 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="CITEREFBergTymoczko,_Stryer2002" class="citation book cs1">Berg, Jeremy M.; Tymoczko, Stryer (2002). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/biochemistrychap00jere"><i>Biochemistry</i></a></span> (5th ed.). New York: <a href="/wiki/W.H._Freeman_and_Company" class="mw-redirect" title="W.H. Freeman and Company">W.H. Freeman and Company</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-7167-3051-0" title="Special:BookSources/0-7167-3051-0"><bdi>0-7167-3051-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=New+York&rft.edition=5th&rft.pub=W.H.+Freeman+and+Company&rft.date=2002&rft.isbn=0-7167-3051-0&rft.aulast=Berg&rft.aufirst=Jeremy+M.&rft.au=Tymoczko%2C+Stryer&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fbiochemistrychap00jere&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" 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="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" class="Z3988"></span></span> </li> <li id="cite_note-enolate-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-enolate_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFManfred_Braun2015" class="citation book cs1">Manfred Braun (2015). <i>Modern Enolate Chemistry: From Preparation to Applications in Asymmetric Synthesis</i>. 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Oxford University Press. pp. 456–459.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=456-459&rft.pub=Oxford+University+Press&rft.date=2012&rft.aulast=Clayden&rft.aufirst=Jonathan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEnol" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhouWangXingWang2013" class="citation journal cs1">Zhou, Yu-Qiang; Wang, Nai-Xing; Xing, Yalan; Wang, Yan-Jing; Hong, Xiao-Wei; Zhang, Jia-Xiang; Chen, Dong-Dong; Geng, Jing-Bo; Dang, Yanfeng; Wang, Zhi-Xiang (2013-01-14). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3544012">"Stable acyclic aliphatic solid enols: synthesis, characterization, X-ray structure analysis and 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