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class="vector-toc-numb">2</span> <span>Example</span> </div> </a> <ul id="toc-Example-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Etymology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Etymology</span> </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-tert-Butyl_effect" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#tert-Butyl_effect"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span><i>tert</i>-Butyl effect</span> </div> </a> <ul id="toc-tert-Butyl_effect-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-tert-Butyl_as_protecting_group" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#tert-Butyl_as_protecting_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span><i>tert</i>-Butyl as protecting group</span> </div> </a> <button aria-controls="toc-tert-Butyl_as_protecting_group-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 <i>tert</i>-Butyl as protecting group subsection</span> </button> <ul id="toc-tert-Butyl_as_protecting_group-sublist" class="vector-toc-list"> <li id="toc-Protection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protection"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Protection</span> </div> </a> <ul id="toc-Protection-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deprotection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deprotection"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Deprotection</span> </div> </a> <ul id="toc-Deprotection-sublist" class="vector-toc-list"> </ul> </li> </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">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of 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Available in 21 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-21" 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">21 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/%D9%85%D8%AC%D9%85%D9%88%D8%B9%D8%A9_%D8%A8%D9%88%D8%AA%D9%8A%D9%84" title="مجموعة بوتيل – Arabic" lang="ar" hreflang="ar" data-title="مجموعة بوتيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Butil_grupa" title="Butil grupa – Bosnian" lang="bs" hreflang="bs" data-title="Butil grupa" 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/Butil" title="Butil – Catalan" lang="ca" hreflang="ca" data-title="Butil" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Butylgruppe" title="Butylgruppe – German" lang="de" hreflang="de" data-title="Butylgruppe" 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/But%C3%BC%C3%BClr%C3%BChm" title="Butüülrühm – Estonian" lang="et" hreflang="et" data-title="Butüülrühm" 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%92%CE%BF%CF%85%CF%84%CF%85%CE%BB%CE%BF%CE%BC%CE%AC%CE%B4%CE%B1" title="Βουτυλομάδα – Greek" lang="el" hreflang="el" data-title="Βουτυλομάδα" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</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%A8%D9%88%D8%AA%DB%8C%D9%84" title="گروه بوتیل – Persian" lang="fa" hreflang="fa" data-title="گروه بوتیل" 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/Butyle" title="Butyle – French" lang="fr" hreflang="fr" data-title="Butyle" 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/B%C3%BAitil" title="Búitil – Irish" lang="ga" hreflang="ga" data-title="Búitil" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Butile" title="Butile – Italian" lang="it" hreflang="it" data-title="Butile" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%91%D1%83%D1%82%D0%B8%D0%BB" title="Бутил – Kazakh" lang="kk" hreflang="kk" data-title="Бутил" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Butylgroep" title="Butylgroep – Dutch" lang="nl" hreflang="nl" data-title="Butylgroep" 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%83%96%E3%83%81%E3%83%AB%E5%9F%BA" title="ブチル基 – Japanese" lang="ja" hreflang="ja" data-title="ブチル基" 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-pl mw-list-item"><a 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical group (−C₄H₉) derived from butane</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">"Butyl" redirects here. For the synthetic rubber, see <a href="/wiki/Butyl_rubber" title="Butyl rubber">Butyl rubber</a>.</div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>butyl</b> is a four-<a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> or <a href="/wiki/Substituent" title="Substituent">substituent group</a> with general <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <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">4</sub>H<sub class="template-chem2-sub">9</sub></span>, derived from either of the two <a href="/wiki/Isomer" title="Isomer">isomers</a> (<i>n</i>-butane and isobutane) of <a href="/wiki/Butane" title="Butane">butane</a>. </p><p>The isomer <i>n</i>-butane can connect in two ways, giving rise to two "-butyl" groups: </p> <ul><li>If it connects at one of the two terminal carbon <a href="/wiki/Atom" title="Atom">atoms</a>, it is <b>normal butyl</b> or <b><i>n</i>-butyl</b>: <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> (preferred IUPAC name: <b>butyl</b>)</li> <li>If it connects at one of the non-terminal (internal) carbon atoms, it is <b>secondary butyl</b> or <b><i>sec</i>-butyl</b>: <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> (preferred IUPAC name: butan-2-yl)</li></ul> <p>The second isomer of butane, isobutane, can also connect in two ways, giving rise to two additional groups: </p> <ul><li>If it connects at one of the three terminal carbons, it is <b>isobutyl</b>: <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> (preferred IUPAC name: 2-methylpropyl)</li> <li>If it connects at the central carbon, it is <b>tertiary butyl</b>, <b><i>tert</i>-butyl</b> or <b><i>t</i>-butyl</b>: <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> (preferred IUPAC name: <i>tert</i>-butyl)</li></ul> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a>, "isobutyl", "<i>sec</i>-butyl", and "<i>tert</i>-butyl" used to be allowed retained names. The latest guidance changed that: only <i>tert</i>-butyl is kept as preferred prefix, all other butyl-names are removed. In the convention of <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formulas</a>, every line ending and line intersection specifies a carbon atom (unless otherwise indicated) saturated with single-linked <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms (unless otherwise indicated). The "R" symbol indicates any <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> or other non-specific functional group. </p> <table class="wikitable"> <tbody><tr> <th><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of butyl<br />(here connected to an R group) </th> <th><a href="/wiki/Trivial_name" title="Trivial name">Common name</a> </th> <th>Preferred<br /><a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> name </th> <th>Alternate notation </th> <th>Fully <a href="/wiki/Systematic_name" title="Systematic name">systematic name</a> </th> <th><a href="/wiki/Skeletal_formula#Alkyl_groups" title="Skeletal formula">Symbol</a> </th></tr> <tr> <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> <td><i>n</i>-butyl </td> <td>butyl </td> <td>butyl </td> <td>butan-1-yl </td> <td>Bu, <i>n</i>-Bu, <i>n</i>Bu, <sup><i>n</i></sup>Bu </td></tr> <tr> <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> <td><i>sec</i>-butyl </td> <td>butan-2-yl </td> <td>1-methylpropyl </td> <td>butan-2-yl </td> <td><i>s</i>-Bu, <i>s</i>Bu, <sup><i>s</i></sup>Bu </td></tr> <tr> <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> <td>isobutyl, <i>iso</i>-butyl </td> <td>2-methylpropyl </td> <td>2-methylpropyl </td> <td>2-methylpropan-1-yl </td> <td><i>i</i>-Bu, <i>i</i>Bu, <sup><i>i</i></sup>Bu </td></tr> <tr> <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/60px-Tert-Butyl-Skeletal-SVG.svg.png" decoding="async" width="60" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Tert-Butyl-Skeletal-SVG.svg/90px-Tert-Butyl-Skeletal-SVG.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Tert-Butyl-Skeletal-SVG.svg/120px-Tert-Butyl-Skeletal-SVG.svg.png 2x" data-file-width="96" data-file-height="90" /></a></span> </td> <td><i>tert</i>-butyl </td> <td><i>tert</i>-butyl </td> <td>1,1-dimethylethyl </td> <td>2-methylpropan-2-yl </td> <td><i>t</i>-Bu, <i>t</i>Bu, <sup><i>t</i></sup>Bu </td></tr></tbody></table> <p>Butyl is the largest substituent for which <a href="/wiki/Trivial_name" title="Trivial name">trivial names</a> are commonly used for all isomers. </p><p>The butyl group's carbon that is connected to the rest (R) of the molecule is called the R<sup>I</sup> or R-prime carbon <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. (January 2011)">citation needed</span></a></i>]</sup>. The prefixes <i>sec</i> (from "secondary") and <i>tert</i> (from "tertiary") refer to the number of additional <a href="/wiki/Side_chain" title="Side chain">side chains</a> (or carbons) connected to the first butyl carbon. The prefix "iso" or "<i>iso</i>" means "isolated" while the prefix '<i>n-</i>' stands for "normal". </p><p>Butan-2-yl (<i>sec</i>-butyl) group is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>. The carbon atom at position 2 is a <a href="/wiki/Stereocenter" title="Stereocenter">stereocenter</a>. It has four different groups attached: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−H</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span>, <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>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−R</span> (the R group is not equal to those three groups). The names of the two chiral groups are: (2<i>S</i>)-butan-2-yl and (2<i>R</i>)-butan-2-yl. </p> <div class="mw-heading mw-heading2"><h2 id="Example">Example</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=2" title="Edit section: Example"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The four isomers (ignoring <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a>) of "<a href="/wiki/Butyl_acetate" title="Butyl acetate">butyl acetate</a>" demonstrate these four isomeric configurations. Here, the acetate radical appears in each of the positions where the "R" symbol is used in the chart above: </p> <table> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Butylacetat.svg" class="mw-file-description" title="butyl acetate"><img alt="butyl acetate" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/200px-Butylacetat.svg.png" decoding="async" width="200" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/300px-Butylacetat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/400px-Butylacetat.svg.png 2x" data-file-width="264" data-file-height="103" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Sec-butyl_acetate.svg" class="mw-file-description" title="sec-butyl acetate"><img alt="sec-butyl acetate" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sec-butyl_acetate.svg/150px-Sec-butyl_acetate.svg.png" decoding="async" width="150" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sec-butyl_acetate.svg/225px-Sec-butyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Sec-butyl_acetate.svg/300px-Sec-butyl_acetate.svg.png 2x" data-file-width="1058" data-file-height="500" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isobutyl_acetate.svg" class="mw-file-description" title="isobutyl acetate"><img alt="isobutyl acetate" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Isobutyl_acetate.svg/150px-Isobutyl_acetate.svg.png" decoding="async" width="150" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Isobutyl_acetate.svg/225px-Isobutyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Isobutyl_acetate.svg/300px-Isobutyl_acetate.svg.png 2x" data-file-width="516" data-file-height="326" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Tert-Butylacetat.svg" class="mw-file-description" title="tert-butyl acetate"><img alt="tert-butyl acetate" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tert-Butylacetat.svg/120px-Tert-Butylacetat.svg.png" decoding="async" width="120" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tert-Butylacetat.svg/180px-Tert-Butylacetat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Tert-Butylacetat.svg/240px-Tert-Butylacetat.svg.png 2x" data-file-width="101" data-file-height="65" /></a></span> </td></tr> <tr> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><a href="/wiki/Butyl_acetate" title="Butyl acetate"><i>n</i>-butyl acetate</a></div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><a href="/wiki/Sec-Butyl_acetate" title="Sec-Butyl acetate"><i>sec</i>-butyl acetate</a></div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><a href="/wiki/Isobutyl_acetate" title="Isobutyl acetate">isobutyl acetate</a></div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><a href="/wiki/Tert-Butyl_acetate" title="Tert-Butyl acetate"><i>tert</i>-butyl acetate</a></div> </td></tr></tbody></table> <p><i>sec</i>-Butyl acetate is chiral, and has one stereocenter, and two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>. The names of enantiomers are: </p> <ul><li>[(2<i>S</i>)-butan-2-yl] acetate, (+)-<i>sec</i>-Butyl acetate</li> <li>[(2<i>R</i>)-butan-2-yl] acetate, (-)-<i>sec</i>-Butyl acetate</li></ul> <p>Therefore, for butyl acetate, the total number of isomers is five, if stereoisomers are included. </p> <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=Butyl_group&action=edit&section=3" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkyl radicals are often considered as a series, a progression sequenced by the number of carbon atoms involved. In that progression, Butyl (containing 4 carbon atoms) is the fourth, and the last with preferred IUPAC name derived from its history. The word "butyl" is derived from <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>, a four-carbon <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> found in <a href="/wiki/Rancidification" title="Rancidification">rancid</a> <a href="/wiki/Butter" title="Butter">butter</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 name "butyric acid" comes from <a href="/wiki/Latin" title="Latin">Latin</a> <i>butyrum</i>, <b>butter</b>. Subsequent preferred IUPAC names for alkyl radicals in the series are simply named from the <a href="/wiki/Greek_language" title="Greek language">Greek</a> number that indicates the number of carbon atoms in the group: <a href="/wiki/Pentyl" class="mw-redirect" title="Pentyl">pentyl</a>, <a href="/wiki/Hexane" title="Hexane">hexyl</a>, <a href="/wiki/Heptane" title="Heptane">heptyl</a>, etc. </p> <div class="mw-heading mw-heading2"><h2 id="tert-Butyl_effect"><i>tert</i>-Butyl effect</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=4" title="Edit section: tert-Butyl effect"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <i>tert</i>-butyl <a href="/wiki/Substituent" title="Substituent">substituent</a> is very bulky and is used in chemistry for <a href="/wiki/Kinetic_reaction_control" class="mw-redirect" title="Kinetic reaction control">kinetic stabilization</a>, as are other bulky groups such as the related <a href="/wiki/Trimethylsilyl" class="mw-redirect" title="Trimethylsilyl">trimethylsilyl</a> group. The effect of the <i>tert</i>-butyl group on the progress of a chemical reaction is called the <a href="/wiki/Thorpe%E2%80%93Ingold_effect" title="Thorpe–Ingold effect">Thorpe–Ingold effect</a> illustrated in the <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a> below. Compared to a hydrogen substituent, the <i>tert</i>-butyl substituent accelerates the <a href="/wiki/Reaction_rate" title="Reaction rate">reaction rate</a> by a factor of 240.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tertbutyleffect.svg" class="mw-file-description" title="tert-Butyl effect"><img alt="tert-Butyl effect" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Tertbutyleffect.svg/400px-Tertbutyleffect.svg.png" decoding="async" width="400" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Tertbutyleffect.svg/600px-Tertbutyleffect.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Tertbutyleffect.svg/800px-Tertbutyleffect.svg.png 2x" data-file-width="419" data-file-height="164" /></a><figcaption><i>tert</i>-Butyl effect</figcaption></figure> <p>The <i>tert</i>-butyl effect is an example of <a href="/wiki/Steric_effects#Steric_hindrance" title="Steric effects">steric hindrance</a>. </p> <div class="mw-heading mw-heading2"><h2 id="tert-Butyl_as_protecting_group"><i>tert</i>-Butyl as protecting group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=5" title="Edit section: tert-Butyl as protecting group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <i>tert</i>-butyl (<i>t</i>Bu) ether is an acid-labile protecting group for alcohols.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Protection">Protection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=6" title="Edit section: Protection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A traditional way to introduce the <i>t</i>Bu group to a hydroxyl group is by treating the compound with <a href="/wiki/Isobutylene" title="Isobutylene">isobutylene</a> in the presence of a <a href="/wiki/Br%C3%B8nsted_acid" class="mw-redirect" title="Brønsted acid">Brønsted acid</a> or <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a>.<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><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> <div class="mw-heading mw-heading3"><h3 id="Deprotection">Deprotection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Butyl_group&action=edit&section=7" title="Edit section: Deprotection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Various acids can be used to cleave the <i>t</i>Bu group, including both Brønsted acids such as <a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">trifluoroacetic acid</a> and Lewis acids such as <a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">titanium tetrachloride</a>.<sup id="cite_ref-:0_3-1" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <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=Butyl_group&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><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="CITEREFHarper" class="citation web cs1">Harper, Douglas. <a rel="nofollow" class="external text" href="http://www.dictionary.com/cite.html?qh=butane&ia=etymon2">"butane. Dictionary.com"</a><span class="reference-accessdate">. Retrieved <span class="nowrap">9 Mar</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=butane.+Dictionary.com&rft.aulast=Harper&rft.aufirst=Douglas&rft_id=http%3A%2F%2Fwww.dictionary.com%2Fcite.html%3Fqh%3Dbutane%26ia%3Detymon2&rfr_id=info%3Asid%2Fen.wikipedia.org%3AButyl+group" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged October 2019">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><i>Factors affecting ease of ring formation. The effect of anchoring substitution on the rate of an intramolecular diels-alder reaction with furan-diene</i> Serge Cauwberghs and Pierre J. De Clercq B. Tinant and J. P. Declercq <a href="/wiki/Tetrahedron_Letters" title="Tetrahedron Letters">Tetrahedron Letters</a> Volume 29, Issue 20 , <b>1988</b>, Pages 2493-2496 <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2800%2987916-2">10.1016/S0040-4039(00)87916-2</a></span> </li> <li id="cite_note-:0-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWutsGreene,_T.W.2006" class="citation book cs1">Wuts, P. G. M.; Greene, T.W. (2006). <i>Greene's Protective Groups in Organic Synthesis</i>. NY: J. Wiley. <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%2F0470053488">10.1002/0470053488</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470053485" title="Special:BookSources/9780470053485"><bdi>9780470053485</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Greene%27s+Protective+Groups+in+Organic+Synthesis&rft.place=NY&rft.pub=J.+Wiley&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F0470053488&rft.isbn=9780470053485&rft.aulast=Wuts&rft.aufirst=P.+G.+M.&rft.au=Greene%2C+T.W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AButyl+group" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMicheliHojosCohenParrish1975" class="citation journal cs1">Micheli, Robert A.; Hojos, Zoltan G.; Cohen, Noal; Parrish, David R.; Portland, Louis A.; Sciamanna, Werner; Scott, Melinda A.; Wehrli, Pius A. (March 1975). <a rel="nofollow" class="external text" href="https://doi.org/10.1021/jo00894a003">"Total syntheses of optically active 19-nor steroids. (+)-Estr-4-ene-3,17-dione and (+)-13.beta.-ethylgon-4-ene-3,17-dione"</a>. <i>The Journal of Organic Chemistry</i>. <b>40</b> (6): 675–681. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00894a003">10.1021/jo00894a003</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Total+syntheses+of+optically+active+19-nor+steroids.+%28%2B%29-Estr-4-ene-3%2C17-dione+and+%28%2B%29-13.beta.-ethylgon-4-ene-3%2C17-dione&rft.volume=40&rft.issue=6&rft.pages=675-681&rft.date=1975-03&rft_id=info%3Adoi%2F10.1021%2Fjo00894a003&rft.issn=0022-3263&rft.aulast=Micheli&rft.aufirst=Robert+A.&rft.au=Hojos%2C+Zoltan+G.&rft.au=Cohen%2C+Noal&rft.au=Parrish%2C+David+R.&rft.au=Portland%2C+Louis+A.&rft.au=Sciamanna%2C+Werner&rft.au=Scott%2C+Melinda+A.&rft.au=Wehrli%2C+Pius+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%2Fjo00894a003&rfr_id=info%3Asid%2Fen.wikipedia.org%3AButyl+group" 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 class="citation journal cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.1039/PS9610000229">"Proceedings of the Chemical Society. July 1961"</a>. <i>Proceedings of the Chemical Society</i> (July): 249. 1 January 1961. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FPS9610000229">10.1039/PS9610000229</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0369-8718">0369-8718</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Chemical+Society&rft.atitle=Proceedings+of+the+Chemical+Society.+July+1961&rft.issue=July&rft.pages=249&rft.date=1961-01-01&rft_id=info%3Adoi%2F10.1039%2FPS9610000229&rft.issn=0369-8718&rft_id=https%3A%2F%2Fdoi.org%2F10.1039%2FPS9610000229&rfr_id=info%3Asid%2Fen.wikipedia.org%3AButyl+group" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style 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aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a class="mw-selflink selflink">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><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" 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