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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Acetalisation_and_ketalization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Acetalisation_and_ketalization"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Acetalisation and ketalization</span> </div> </a> <ul id="toc-Acetalisation_and_ketalization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Examples</span> </div> </a> <button aria-controls="toc-Examples-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 Examples subsection</span> </button> <ul id="toc-Examples-sublist" class="vector-toc-list"> <li id="toc-Sugars" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sugars"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Sugars</span> </div> </a> <ul id="toc-Sugars-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chiral_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chiral_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Chiral derivatives</span> </div> </a> <ul id="toc-Chiral_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Formaldehyde_and_acetaldehyde" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Formaldehyde_and_acetaldehyde"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Formaldehyde and acetaldehyde</span> </div> </a> <ul id="toc-Formaldehyde_and_acetaldehyde-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Unusual_acetals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Unusual_acetals"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Unusual acetals</span> </div> </a> <ul id="toc-Unusual_acetals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Flavors_and_fragrances" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Flavors_and_fragrances"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Flavors and fragrances</span> </div> </a> <ul id="toc-Flavors_and_fragrances-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Related_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Related_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Related compounds</span> </div> </a> <ul id="toc-Related_compounds-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">4</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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span 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Available in 36 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-36" 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">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AA%D8%A7%D9%84" title="أسيتال – Arabic" lang="ar" hreflang="ar" data-title="أسيتال" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acetal" title="Acetal – Catalan" lang="ca" hreflang="ca" data-title="Acetal" 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/Acetal" title="Acetal – Czech" lang="cs" hreflang="cs" data-title="Acetal" 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/Acetale" title="Acetale – German" lang="de" hreflang="de" data-title="Acetale" 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/Atsetaalid" title="Atsetaalid – Estonian" lang="et" hreflang="et" data-title="Atsetaalid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Acetal" title="Acetal – Spanish" lang="es" hreflang="es" data-title="Acetal" 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/Azetal" title="Azetal – Basque" lang="eu" hreflang="eu" data-title="Azetal" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%A7%D9%84" title="استال – Persian" lang="fa" hreflang="fa" data-title="استال" 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/Ac%C3%A9tal_et_c%C3%A9tal" title="Acétal et cétal – French" lang="fr" hreflang="fr" data-title="Acétal et cétal" 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/Acetal" title="Acetal – Galician" lang="gl" hreflang="gl" data-title="Acetal" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%83%88" title="아세탈 – Korean" lang="ko" hreflang="ko" data-title="아세탈" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%B8%E0%A4%BF%E0%A4%9F%E0%A4%B2" title="एसिटल – Hindi" lang="hi" hreflang="hi" data-title="एसिटल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Acetal" title="Acetal – Croatian" lang="hr" hreflang="hr" data-title="Acetal" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acetali" title="Acetali – Italian" lang="it" hreflang="it" data-title="Acetali" 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%A6%D7%98%D7%9C" title="אצטל – Hebrew" lang="he" hreflang="he" data-title="אצטל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%85%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B2%BE%E0%B2%B2%E0%B3%8D" title="ಅಸಿಟಾಲ್ – Kannada" lang="kn" hreflang="kn" data-title="ಅಸಿಟಾಲ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Acet%C3%A1l" title="Acetál – Hungarian" lang="hu" hreflang="hu" data-title="Acetál" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB" title="Ацетал – Macedonian" lang="mk" hreflang="mk" data-title="Ацетал" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%B8%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%BE%E0%B5%BD" title="അസറ്റാൽ – Malayalam" lang="ml" hreflang="ml" data-title="അസറ്റാൽ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Acetaal" title="Acetaal – Dutch" lang="nl" hreflang="nl" data-title="Acetaal" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%BB%E3%82%BF%E3%83%BC%E3%83%AB" title="アセタール – Japanese" lang="ja" hreflang="ja" data-title="アセタール" 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/Acetal" title="Acetal – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Acetal" 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/Acetal" title="Acetal – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Acetal" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Atsetallar" title="Atsetallar – Uzbek" lang="uz" hreflang="uz" data-title="Atsetallar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Acetale" title="Acetale – Polish" lang="pl" hreflang="pl" data-title="Acetale" 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/Acetal" title="Acetal – Portuguese" lang="pt" hreflang="pt" data-title="Acetal" 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/Acetal" title="Acetal – Romanian" lang="ro" hreflang="ro" data-title="Acetal" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D0%B8" title="Ацетали – Russian" lang="ru" hreflang="ru" data-title="Ацетали" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acet%C3%A1l" title="Acetál – Slovak" lang="sk" hreflang="sk" data-title="Acetál" 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/Acetal" title="Acetal – Serbian" lang="sr" hreflang="sr" data-title="Acetal" 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/Acetal" title="Acetal – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Acetal" 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/Asetaalit" title="Asetaalit – Finnish" lang="fi" hreflang="fi" data-title="Asetaalit" 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/Acetal" title="Acetal – Swedish" lang="sv" hreflang="sv" data-title="Acetal" 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/Asetal" title="Asetal – Turkish" lang="tr" hreflang="tr" data-title="Asetal" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D1%96" title="Ацеталі – Ukrainian" lang="uk" hreflang="uk" data-title="Ацеталі" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%BC%A9%E9%86%9B" title="缩醛 – Chinese" lang="zh" hreflang="zh" data-title="缩醛" 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/Q421103#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li 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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">Organic compound with the structure >C(O–)2</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For the engineering plastic, see <a href="/wiki/Polyoxymethylene" title="Polyoxymethylene">Polyoxymethylene</a>. For the flavor compound, see <a href="/wiki/1,1-Diethoxyethane" title="1,1-Diethoxyethane">1,1-diethoxyethane</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a>.</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acetal_general_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetal_general_structure.svg/220px-Acetal_general_structure.svg.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetal_general_structure.svg/330px-Acetal_general_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetal_general_structure.svg/440px-Acetal_general_structure.svg.png 2x" data-file-width="680" data-file-height="400" /></a><figcaption>Generic structure of acetals</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>acetal</b> is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> with the connectivity <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C(OR')<sub class="template-chem2-sub">2</sub></span>. Here, the R groups can be organic fragments (a <a href="/wiki/Carbon" title="Carbon">carbon</a> atom, with arbitrary other atoms attached to that) or <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> or <a href="/wiki/Ketone" title="Ketone">ketones</a> and have the same <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> at the central carbon, but have substantially different <a href="/wiki/Chemical_stability" title="Chemical stability">chemical stability</a> and <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactivity</a> as compared to the analogous <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> compounds. The central carbon atom has four bonds to it, and is therefore <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated</a> and has <a href="/wiki/Tetrahedral_geometry" class="mw-redirect" title="Tetrahedral geometry">tetrahedral geometry</a>. </p><p>The term <b>ketal</b> is sometimes used to identify structures associated with <a href="/wiki/Ketone" title="Ketone">ketones</a> (both R groups organic fragments rather than hydrogen) rather than <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> and, historically, the term <b>acetal</b> was used specifically for the aldehyde-related cases (having at least one hydrogen in place of an R on the central carbon).<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 IUPAC originally deprecated the usage of the word ketal altogether, but has since reversed its decision. However, in contrast to historical usage, ketals are now a subset of acetals, a term that now encompasses both aldehyde- and ketone-derived structures. </p><p>If one of the R groups has an oxygen as the first atom (that is, there are more than two oxygens single-bonded to the central carbon), the functional group is instead an <a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">orthoester</a>. In contrast to variations of R, both R' groups are organic fragments. If one R' is a hydrogen, the functional group is instead a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a>, while if both are H, the functional group is a ketone <a href="/wiki/Hydrate" title="Hydrate">hydrate</a> or aldehyde hydrate. </p><p>Formation of an acetal occurs when the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group of a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> becomes <a href="/wiki/Protonation" title="Protonation">protonated</a> and is lost as water. The <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> that is produced is then rapidly attacked by a molecule of <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. Loss of the proton from the attached alcohol gives the acetal. </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .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 tnone center"><div class="thumbinner multiimageinner" style="width:420px;max-width:420px"><div class="trow"><div class="tsingle" style="width:418px;max-width:418px"><div class="thumbimage" style="height:94px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Acetal_formation_2.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Acetal_formation_2.png/416px-Acetal_formation_2.png" decoding="async" width="416" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Acetal_formation_2.png/624px-Acetal_formation_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Acetal_formation_2.png/832px-Acetal_formation_2.png 2x" data-file-width="857" data-file-height="194" /></a></span></div><div class="thumbcaption text-align-center">Aldehyde to acetal conversion</div></div></div><div class="trow"><div class="tsingle" style="width:418px;max-width:418px"><div class="thumbimage" style="height:94px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Ketal_formation.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Ketal_formation.png/416px-Ketal_formation.png" decoding="async" width="416" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Ketal_formation.png/624px-Ketal_formation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Ketal_formation.png/832px-Ketal_formation.png 2x" data-file-width="857" data-file-height="194" /></a></span></div><div class="thumbcaption text-align-center">Ketone to ketal conversion</div></div></div></div></div> <p>Acetals are stable compared to hemiacetals but their formation is a reversible <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> as with <a href="/wiki/Ester" title="Ester">esters</a>. As a reaction to create an acetal proceeds, water must be removed from the reaction mixture, for example, with a <a href="/wiki/Dean%E2%80%93Stark_apparatus" title="Dean–Stark apparatus">Dean–Stark apparatus</a>, lest it <a href="/wiki/Hydrolyse" class="mw-redirect" title="Hydrolyse">hydrolyse</a> the product back to the hemiacetal. The formation of acetals reduces the total number of molecules present (carbonyl + 2 alcohol → acetal + water) and therefore is generally not favourable with regards to <a href="/wiki/Entropy" title="Entropy">entropy</a>. One situation where it is not entropically unfavourable is when a single <a href="/wiki/Diol" title="Diol">diol</a> molecule is used rather than two separate alcohol molecules (carbonyl + diol → acetal + water). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Acetalisation_and_ketalization">Acetalisation and ketalization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=1" title="Edit section: Acetalisation and ketalization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="anchor" id="Acetalisation"></span> Acetalisation and ketalization are the <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a> that involve the formation of an acetal (or ketals) from aldehydes and ketones, respectively. These conversions are <a href="/wiki/Acid" title="Acid">acid</a> <a href="/wiki/Catalysis" title="Catalysis">catalysed</a>. They eliminate water. Since each step is often a rapid equilibrium, the reaction must be driven by removal of water. Methods for removing water include <a href="/wiki/Azeotropic_distillation" title="Azeotropic distillation">azeotropic distillation</a> and trapping water with desiccants like <a href="/wiki/Aluminium_oxide" title="Aluminium oxide">aluminium oxide</a> and <a href="/wiki/Molecular_sieve" title="Molecular sieve">molecular sieves</a>. Steps assumed to be involved: protonation of the carbonyl oxygen, addition of the alcohol to the protonated carbonyl, protonolysis of the resulting <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> or hemiketal, and addition of the second alcohol. These steps are illustrated with an aldehyde RCH=O and the alcohol R'OH: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH=O + H<sup class="template-chem2-sup">+</sup> ⇌ RCH=OH<sup class="template-chem2-sup">+</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH=OH<sup class="template-chem2-sup">+</sup> + R'OH ⇌ RCH(OH)(OR') + H<sup class="template-chem2-sup">+</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH(OH)(OR') + H<sup class="template-chem2-sup">+</sup> ⇌ RC<sup class="template-chem2-sup">+</sup>H(OR') + H<sub class="template-chem2-sub">2</sub>O</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RC<sup class="template-chem2-sup">+</sup>H(OR') + R'OH ⇌ RCH(OR')<sub class="template-chem2-sub">2</sub> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>Another way to avoid the entropic cost is to perform the synthesis by acetal exchange, using a pre-existing acetal-type reagent as the OR'-group donor rather than simple addition of alcohols themselves. One type of reagent used for this method is an orthoester. In this case, water produced along with the acetal product is destroyed when it hydrolyses residual orthoester molecules, and this <a href="/wiki/Side_reaction" title="Side reaction">side reaction</a> also produces more alcohol to be used in the main reaction. </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=2" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Sugars">Sugars</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=3" title="Edit section: Sugars"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since many sugars are polyhydroxy aldehydes and ketones, sugars are a rich source of acetals and ketals. Most <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bonds</a> in <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and other <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> are acetal linkages.<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> <a href="/wiki/Cellulose" title="Cellulose">Cellulose</a> is a ubiquitous example of a polyacetal. </p><p><a href="/wiki/Benzylidene_acetal" title="Benzylidene acetal">Benzylidene acetal</a> and <a href="/wiki/Acetonide" title="Acetonide">acetonide</a> as protecting groups used in research of modified sugars. </p> <div class="mw-heading mw-heading3"><h3 id="Chiral_derivatives">Chiral derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=4" title="Edit section: Chiral derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetals also find application as <a href="/w/index.php?title=Chirality_(chem)&action=edit&redlink=1" class="new" title="Chirality (chem) (page does not exist)">chiral</a> auxiliaries. Indeed acetals of chiral glycols like, e.g. derivatives of tartaric acid can be asymmetrically opened with high selectivity. This enables the construction of new chiral centers.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lardolure_is.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Lardolure_is.svg/500px-Lardolure_is.svg.png" decoding="async" width="500" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Lardolure_is.svg/750px-Lardolure_is.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Lardolure_is.svg/1000px-Lardolure_is.svg.png 2x" data-file-width="1266" data-file-height="410" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Formaldehyde_and_acetaldehyde">Formaldehyde and acetaldehyde</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=5" title="Edit section: Formaldehyde and acetaldehyde"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde forms a rich collection of acetals. This tendency reflects the fact that low molecular weight aldehydes are prone to self-condensation such that the C=O bond is replaced by an acetal. The acetal formed from <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> (two hydrogens attached to the central carbon) is sometimes called a <i>formal</i><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> or the <a href="/wiki/Methylenedioxy" title="Methylenedioxy">methylenedioxy</a> group. The acetal formed from <a href="/wiki/Acetone" title="Acetone">acetone</a> is sometimes called an <a href="/wiki/Acetonide" title="Acetonide">acetonide</a>. Formaldehyde forms <a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a> and <a href="/wiki/1,3,5-Trioxane" title="1,3,5-Trioxane">1,3,5-Trioxane</a>. <a href="/wiki/Polyoxymethylene" title="Polyoxymethylene">Polyoxymethylene</a> (POM) plastic, also known as "acetal" or "polyacetal", is a polyacetal (and a polyether), and a polymer of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>. <a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a> converts to <a href="/wiki/Metaldehyde" title="Metaldehyde">Metaldehyde</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Unusual_acetals">Unusual acetals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=6" title="Edit section: Unusual acetals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/w/index.php?title=Phenylsulfonylethylidene&action=edit&redlink=1" class="new" title="Phenylsulfonylethylidene (page does not exist)">Phenylsulfonylethylidene</a> (PSE) acetal is an example of arylsulfonyl acetal possessing atypical properties, like resistance to acid hydrolysis which leads to selective introduction and removal of the protective group.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Flavors_and_fragrances">Flavors and fragrances</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=7" title="Edit section: Flavors and fragrances"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/1,1-Diethoxyethane" title="1,1-Diethoxyethane">1,1-Diethoxyethane</a> (acetaldehyde diethyl acetal), sometimes called simply "acetal", is an important flavouring compound in <a href="/wiki/Distilled_beverage" class="mw-redirect" title="Distilled beverage">distilled beverages</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Two ketals of ethyl acetoacetate are used in commercial fragrances.<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> <a href="/wiki/Fructone" title="Fructone">Fructone</a> (<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<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>)CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">5</sub></span>), an ethylene glycol ketal, and fraistone (<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<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">3</sub>)CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">5</sub></span>), a propylene glycol ketal, are commercial fragrances. </p> <div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetal&action=edit&section=8" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Used in a more general sense, the term <b>X</b>,<b>Y</b>-<i>acetal</i> also refers to any functional group that consists of a carbon bearing two heteroatoms <b>X</b> and <b>Y</b>. For example, <i>N</i>,<i>O</i>-acetal refers to compounds of type R<sup>1</sup>R<sup>2</sup>C(OR)(NR'<sub>2</sub>) (R,R' ≠ H) also known as a <i>hemiaminal ether</i> or <a href="/wiki/Aminal" title="Aminal">Aminal</a>, a.k.a. aminoacetal. </p><p><i>S</i>,<i>S</i>-acetal refers to compounds of type R<sup>1</sup>R<sup>2</sup>C(SR)(SR') (R,R' ≠ H, also known as <a href="/wiki/Thioacetal" title="Thioacetal">thioacetal</a> and <a href="/wiki/Thioketal" title="Thioketal">thioketals</a>. </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=Acetal&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Hemiaminal" title="Hemiaminal">Hemiaminal</a></li> <li><a href="/wiki/Orthoformate" class="mw-redirect" title="Orthoformate">Orthoformate</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=Acetal&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/K03376.html">ketals</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.K03376">10.1351/goldbook.K03376</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/G02661.html">glycosides</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.G02661">10.1351/goldbook.G02661</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">P.J. Kocieński: <i>Protecting Groups</i>, S. 164–167.</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">Morrison, Robert T. and Boyd, Robert N., "Organic Chemistry (6th ed)". p683. Prentice-Hall Inc (1992).</span> </li> <li id="cite_note-:0-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChéryRollinDe_LucchiCossu2000" class="citation journal cs1">Chéry, Florence; Rollin, Patrick; De Lucchi, Ottorino; Cossu, Sergio (2000). "Phenylsulfonylethylidene (PSE) acetals as atypical carbohydrate-protective groups". <i>Tetrahedron Letters</i>. <b>41</b> (14): 2357–2360. <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%2900199-4">10.1016/s0040-4039(00)00199-4</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/0040-4039">0040-4039</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Phenylsulfonylethylidene+%28PSE%29+acetals+as+atypical+carbohydrate-protective+groups&rft.volume=41&rft.issue=14&rft.pages=2357-2360&rft.date=2000&rft_id=info%3Adoi%2F10.1016%2Fs0040-4039%2800%2900199-4&rft.issn=0040-4039&rft.aulast=Ch%C3%A9ry&rft.aufirst=Florence&rft.au=Rollin%2C+Patrick&rft.au=De+Lucchi%2C+Ottorino&rft.au=Cossu%2C+Sergio&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetal" 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="CITEREFMaarse1991" class="citation book cs1">Maarse, Henk (1991-03-29). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_OvXjhLUz-oC"><i>Volatile Compounds in Foods and Beverages</i></a>. CRC Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8247-8390-7" title="Special:BookSources/978-0-8247-8390-7"><bdi>978-0-8247-8390-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Volatile+Compounds+in+Foods+and+Beverages&rft.pub=CRC+Press&rft.date=1991-03-29&rft.isbn=978-0-8247-8390-7&rft.aulast=Maarse&rft.aufirst=Henk&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_OvXjhLUz-oC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetal" 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="CITEREFPantenSurburg2016" class="citation book cs1">Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. pp. 1–45. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.t11_t02">10.1002/14356007.t11_t02</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Flavors+and+Fragrances%2C+3.+Aromatic+and+Heterocyclic+Compounds&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=1-45&rft.date=2016&rft_id=info%3Adoi%2F10.1002%2F14356007.t11_t02&rft.isbn=978-3-527-30673-2&rft.aulast=Panten&rft.aufirst=Johannes&rft.au=Surburg%2C+Horst&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetal" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist 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href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" 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