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class="vector-toc-link" href="#Common_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Common names</span> </div> </a> <ul id="toc-Common_names-sublist" class="vector-toc-list"> <li id="toc-Primary,_secondary,_and_tertiary" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Primary,_secondary,_and_tertiary"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.1</span> <span>Primary, secondary, and tertiary</span> </div> </a> <ul id="toc-Primary,_secondary,_and_tertiary-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Examples</span> </div> </a> <ul id="toc-Examples-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Physical properties</span> </div> </a> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Occurrence_in_nature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Occurrence_in_nature"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Occurrence in nature</span> </div> </a> <ul id="toc-Occurrence_in_nature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Hydroxylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydroxylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Hydroxylation</span> </div> </a> <ul id="toc-Hydroxylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ziegler_and_oxo_processes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ziegler_and_oxo_processes"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Ziegler and oxo processes</span> </div> </a> <ul id="toc-Ziegler_and_oxo_processes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydration_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydration_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3</span> <span>Hydration reactions</span> </div> </a> <ul id="toc-Hydration_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fermentation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fermentation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.4</span> <span>Fermentation</span> </div> </a> <ul id="toc-Fermentation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.5</span> <span>Substitution</span> </div> </a> <ul id="toc-Substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.6</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.7</span> <span>Hydrolysis</span> </div> </a> <ul id="toc-Hydrolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-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 Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Deprotonation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deprotonation"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Deprotonation</span> </div> </a> <ul id="toc-Deprotonation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Nucleophilic substitution</span> </div> </a> <ul id="toc-Nucleophilic_substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dehydration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydration"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Dehydration</span> </div> </a> <ul id="toc-Dehydration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Protonolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protonolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4</span> <span>Protonolysis</span> </div> </a> <ul id="toc-Protonolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Esterification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esterification"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.5</span> <span>Esterification</span> </div> </a> <ul id="toc-Esterification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.6</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Citations" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Citations"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Citations</span> </div> </a> <ul id="toc-Citations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-General_references" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#General_references"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>General references</span> </div> </a> <ul id="toc-General_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 class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Alcohol (chemistry)</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" 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Available in 130 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-130" 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">130 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Alkohol" title="Alkohol – Afrikaans" lang="af" hreflang="af" data-title="Alkohol" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/Alkohole" title="Alkohole – Alemannic" lang="gsw" hreflang="gsw" data-title="Alkohole" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-anp mw-list-item"><a href="https://anp.wikipedia.org/wiki/%E0%A4%90%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%8B%E0%A4%B9%E0%A5%89%E0%A4%B2" title="ऐल्कोहॉल – Angika" lang="anp" hreflang="anp" data-title="ऐल्कोहॉल" data-language-autonym="अंगिका" data-language-local-name="Angika" class="interlanguage-link-target"><span>अंगिका</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%AD%D9%88%D9%84" title="كحول – Arabic" lang="ar" hreflang="ar" data-title="كحول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Alcol" title="Alcol – Aragonese" lang="an" hreflang="an" data-title="Alcol" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-roa-rup mw-list-item"><a href="https://roa-rup.wikipedia.org/wiki/Alcoolu" title="Alcoolu – Aromanian" lang="rup" hreflang="rup" data-title="Alcoolu" data-language-autonym="Armãneashti" data-language-local-name="Aromanian" class="interlanguage-link-target"><span>Armãneashti</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%8F%E0%A6%B2%E0%A6%95%27%E0%A6%B9%E0%A6%B2" title="এলক'হল – Assamese" lang="as" hreflang="as" data-title="এলক'হল" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Alcohol" title="Alcohol – Asturian" lang="ast" hreflang="ast" data-title="Alcohol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-awa mw-list-item"><a href="https://awa.wikipedia.org/wiki/%E0%A4%85%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%8B%E0%A4%B9%E0%A4%B2" title="अल्कोहल – Awadhi" lang="awa" hreflang="awa" data-title="अल्कोहल" data-language-autonym="अवधी" data-language-local-name="Awadhi" class="interlanguage-link-target"><span>अवधी</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Spirtl%C9%99r" title="Spirtlər – Azerbaijani" lang="az" hreflang="az" data-title="Spirtlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%D9%88%D9%84" title="آلکول – South Azerbaijani" lang="azb" hreflang="azb" data-title="آلکول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%95%E0%A7%8B%E0%A6%B9%E0%A6%B2" title="অ্যালকোহল – Bangla" lang="bn" hreflang="bn" data-title="অ্যালকোহল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Alcohol" title="Alcohol – Minnan" lang="nan" hreflang="nan" data-title="Alcohol" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82" title="Спирт – Bashkir" lang="ba" hreflang="ba" data-title="Спирт" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A1%D0%BF%D1%96%D1%80%D1%82%D1%8B" title="Спірты – Belarusian" lang="be" hreflang="be" data-title="Спірты" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A1%D1%8C%D0%BF%D1%96%D1%80%D1%82" title="Сьпірт – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Сьпірт" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Alkohol" title="Alkohol – Central Bikol" lang="bcl" hreflang="bcl" data-title="Alkohol" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%BE%D1%85%D0%BE%D0%BB" title="Алкохол – Bulgarian" lang="bg" hreflang="bg" data-title="Алкохол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Alkohol" title="Alkohol – Bosnian" lang="bs" hreflang="bs" data-title="Alkohol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Alkool_(kimiezh)" title="Alkool (kimiezh) – Breton" lang="br" hreflang="br" data-title="Alkool (kimiezh)" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Alcohol" title="Alcohol – Catalan" lang="ca" hreflang="ca" data-title="Alcohol" 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/Alkoholy" title="Alkoholy – Czech" lang="cs" hreflang="cs" data-title="Alkoholy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Alcohol" title="Alcohol – Welsh" lang="cy" hreflang="cy" data-title="Alcohol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-dag mw-list-item"><a href="https://dag.wikipedia.org/wiki/Dam" title="Dam – Dagbani" lang="dag" hreflang="dag" data-title="Dam" data-language-autonym="Dagbanli" data-language-local-name="Dagbani" class="interlanguage-link-target"><span>Dagbanli</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alkohol_(stofklasse)" title="Alkohol (stofklasse) – Danish" lang="da" hreflang="da" data-title="Alkohol (stofklasse)" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Alkohole" title="Alkohole – German" lang="de" hreflang="de" data-title="Alkohole" 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/Alkoholid" title="Alkoholid – Estonian" lang="et" hreflang="et" data-title="Alkoholid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CE%BF%CF%8C%CE%BB%CE%B5%CF%82" title="Αλκοόλες – Greek" lang="el" hreflang="el" data-title="Αλκοόλες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alcohol" title="Alcohol – Spanish" lang="es" hreflang="es" data-title="Alcohol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Alkoholo" title="Alkoholo – Esperanto" lang="eo" hreflang="eo" data-title="Alkoholo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Alkohol" title="Alkohol – Basque" lang="eu" hreflang="eu" data-title="Alkohol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D9%84" title="الکل – Persian" lang="fa" hreflang="fa" data-title="الکل" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-hif mw-list-item"><a href="https://hif.wikipedia.org/wiki/Alcohol" title="Alcohol – Fiji Hindi" lang="hif" hreflang="hif" data-title="Alcohol" data-language-autonym="Fiji Hindi" data-language-local-name="Fiji Hindi" class="interlanguage-link-target"><span>Fiji Hindi</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Alkohol" title="Alkohol – Faroese" lang="fo" hreflang="fo" data-title="Alkohol" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Alcool_(chimie)" title="Alcool (chimie) – French" lang="fr" hreflang="fr" data-title="Alcool (chimie)" 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/Alc%C3%B3il" title="Alcóil – Irish" lang="ga" hreflang="ga" data-title="Alcóil" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gv mw-list-item"><a href="https://gv.wikipedia.org/wiki/Alcoal" title="Alcoal – Manx" lang="gv" hreflang="gv" data-title="Alcoal" data-language-autonym="Gaelg" data-language-local-name="Manx" class="interlanguage-link-target"><span>Gaelg</span></a></li><li class="interlanguage-link interwiki-gd mw-list-item"><a href="https://gd.wikipedia.org/wiki/Alcol" title="Alcol – Scottish Gaelic" lang="gd" hreflang="gd" data-title="Alcol" data-language-autonym="Gàidhlig" data-language-local-name="Scottish Gaelic" class="interlanguage-link-target"><span>Gàidhlig</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alcohol" title="Alcohol – Galician" lang="gl" hreflang="gl" data-title="Alcohol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%86%E0%AA%B2%E0%AB%8D%E0%AA%95%E0%AB%8B%E0%AA%B9%E0%AB%8B%E0%AA%B2" title="આલ્કોહોલ – Gujarati" lang="gu" hreflang="gu" data-title="આલ્કોહોલ" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%EC%BD%94%EC%98%AC" title="알코올 – Korean" lang="ko" hreflang="ko" data-title="알코올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8D%D5%BA%D5%AB%D6%80%D5%BF" title="Սպիրտ – Armenian" lang="hy" hreflang="hy" data-title="Սպիրտ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%90%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%8B%E0%A4%B9%E0%A5%89%E0%A4%B2" title="ऐल्कोहॉल – Hindi" lang="hi" hreflang="hi" data-title="ऐल्कोहॉल" 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/Alkoholi" title="Alkoholi – Croatian" lang="hr" hreflang="hr" data-title="Alkoholi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Alkoholo" title="Alkoholo – Ido" lang="io" hreflang="io" data-title="Alkoholo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-ilo mw-list-item"><a href="https://ilo.wikipedia.org/wiki/Alkohol" title="Alkohol – Iloko" lang="ilo" hreflang="ilo" data-title="Alkohol" data-language-autonym="Ilokano" data-language-local-name="Iloko" class="interlanguage-link-target"><span>Ilokano</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkohol" title="Alkohol – Indonesian" lang="id" hreflang="id" data-title="Alkohol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Alcohol" title="Alcohol – Interlingua" lang="ia" hreflang="ia" data-title="Alcohol" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Alk%C3%B3h%C3%B3l" title="Alkóhól – Icelandic" lang="is" hreflang="is" data-title="Alkóhól" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alcoli" title="Alcoli – Italian" lang="it" hreflang="it" data-title="Alcoli" 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%9B%D7%95%D7%94%D7%9C" title="כוהל – Hebrew" lang="he" hreflang="he" data-title="כוהל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Alkohol" title="Alkohol – Javanese" lang="jv" hreflang="jv" data-title="Alkohol" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kbp mw-list-item"><a href="https://kbp.wikipedia.org/wiki/Al%C9%A9k%C9%94%C9%94l%C9%A9" title="Alɩkɔɔlɩ – Kabiye" lang="kbp" hreflang="kbp" data-title="Alɩkɔɔlɩ" data-language-autonym="Kabɩyɛ" data-language-local-name="Kabiye" class="interlanguage-link-target"><span>Kabɩyɛ</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%B2%E0%B3%8D%E0%B2%95%E0%B3%8B%E0%B2%B9%E0%B2%BE%E0%B2%B2%E0%B3%8D" title="ಆಲ್ಕೋಹಾಲ್ – Kannada" lang="kn" hreflang="kn" data-title="ಆಲ್ಕೋಹಾಲ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A1%E1%83%9E%E1%83%98%E1%83%A0%E1%83%A2%E1%83%98" title="სპირტი – Georgian" lang="ka" hreflang="ka" data-title="სპირტი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%BE%D0%B3%D0%BE%D0%BB%D1%8C%D0%B4%D0%B5%D1%80" title="Алкогольдер – Kazakh" lang="kk" hreflang="kk" data-title="Алкогольдер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Alkoholi" title="Alkoholi – Swahili" lang="sw" hreflang="sw" data-title="Alkoholi" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Alk%C3%B2l" title="Alkòl – Haitian Creole" lang="ht" hreflang="ht" data-title="Alkòl" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Alkol" title="Alkol – Kurdish" lang="ku" hreflang="ku" data-title="Alkol" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82" title="Спирт – Kyrgyz" lang="ky" hreflang="ky" data-title="Спирт" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lad mw-list-item"><a href="https://lad.wikipedia.org/wiki/Alk%C3%B3l" title="Alkól – Ladino" lang="lad" hreflang="lad" data-title="Alkól" data-language-autonym="Ladino" data-language-local-name="Ladino" class="interlanguage-link-target"><span>Ladino</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Alcohol" title="Alcohol – Latin" lang="la" hreflang="la" data-title="Alcohol" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Spirti" title="Spirti – Latvian" lang="lv" hreflang="lv" data-title="Spirti" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Alkoholen" title="Alkoholen – Luxembourgish" lang="lb" hreflang="lb" data-title="Alkoholen" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkoholis" title="Alkoholis – Lithuanian" lang="lt" hreflang="lt" data-title="Alkoholis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lij mw-list-item"><a href="https://lij.wikipedia.org/wiki/Alcooli" title="Alcooli – Ligurian" lang="lij" hreflang="lij" data-title="Alcooli" data-language-autonym="Ligure" data-language-local-name="Ligurian" class="interlanguage-link-target"><span>Ligure</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Alcohol" title="Alcohol – Limburgish" lang="li" hreflang="li" data-title="Alcohol" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-ln mw-list-item"><a href="https://ln.wikipedia.org/wiki/Lotoko" title="Lotoko – Lingala" lang="ln" hreflang="ln" data-title="Lotoko" data-language-autonym="Lingála" data-language-local-name="Lingala" class="interlanguage-link-target"><span>Lingála</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Alcol" title="Alcol – Lombard" lang="lmo" hreflang="lmo" data-title="Alcol" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alkoholok" title="Alkoholok – Hungarian" lang="hu" hreflang="hu" data-title="Alkoholok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%BE%D1%85%D0%BE%D0%BB" title="Алкохол – Macedonian" lang="mk" hreflang="mk" data-title="Алкохол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Alikaola_(simia)" title="Alikaola (simia) – Malagasy" lang="mg" hreflang="mg" data-title="Alikaola (simia)" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%9A%E0%B4%BE%E0%B4%B0%E0%B4%BE%E0%B4%AF%E0%B4%82_(%E0%B4%B0%E0%B4%B8%E0%B4%A4%E0%B4%A8%E0%B5%8D%E0%B4%A4%E0%B5%8D%E0%B4%B0%E0%B4%82)" title="ചാരായം (രസതന്ത്രം) – Malayalam" lang="ml" hreflang="ml" data-title="ചാരായം (രസതന്ത്രം)" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D8%A7%D9%84%D9%83%D8%AD%D9%88%D9%84" title="الكحول – Egyptian Arabic" lang="arz" hreflang="arz" data-title="الكحول" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alkohol" title="Alkohol – Malay" lang="ms" hreflang="ms" data-title="Alkohol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Alkohol" title="Alkohol – Minangkabau" lang="min" hreflang="min" data-title="Alkohol" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%A1%E1%80%9A%E1%80%BA%E1%80%9C%E1%80%BA%E1%80%80%E1%80%AD%E1%80%AF%E1%80%9F%E1%80%B1%E1%80%AC" title="အယ်လ်ကိုဟော – Burmese" lang="my" hreflang="my" data-title="အယ်လ်ကိုဟော" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alcohol_(stofklasse)" title="Alcohol (stofklasse) – Dutch" lang="nl" hreflang="nl" data-title="Alcohol (stofklasse)" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%85%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%8B%E0%A4%B9%E0%A4%B2" title="अल्कोहल – Nepali" lang="ne" hreflang="ne" data-title="अल्कोहल" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%B3%E3%83%BC%E3%83%AB" title="アルコール – Japanese" lang="ja" hreflang="ja" data-title="アルコール" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Alkohol" title="Alkohol – Northern Frisian" lang="frr" hreflang="frr" data-title="Alkohol" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alkoholer" title="Alkoholer – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Alkoholer" 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/Alkoholar" title="Alkoholar – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Alkoholar" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Alc%C3%B2l" title="Alcòl – Occitan" lang="oc" hreflang="oc" data-title="Alcòl" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Farshoo_(keemistirii)" title="Farshoo (keemistirii) – Oromo" lang="om" hreflang="om" data-title="Farshoo (keemistirii)" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Spirtlar" title="Spirtlar – Uzbek" lang="uz" hreflang="uz" data-title="Spirtlar" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%85%E0%A8%B2%E0%A8%95%E0%A9%8B%E0%A8%B9%E0%A8%B2" title="ਅਲਕੋਹਲ – Punjabi" lang="pa" hreflang="pa" data-title="ਅਲਕੋਹਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%AD%D9%84" title="الکحل – Western Punjabi" lang="pnb" hreflang="pnb" data-title="الکحل" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D9%88%D9%84" title="الکول – Pashto" lang="ps" hreflang="ps" data-title="الکول" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-jam mw-list-item"><a href="https://jam.wikipedia.org/wiki/Alkoal" title="Alkoal – Jamaican Creole English" lang="jam" hreflang="jam" data-title="Alkoal" data-language-autonym="Patois" data-language-local-name="Jamaican Creole English" class="interlanguage-link-target"><span>Patois</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Alkohol" title="Alkohol – Low German" lang="nds" hreflang="nds" data-title="Alkohol" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkohole" title="Alkohole – Polish" lang="pl" hreflang="pl" data-title="Alkohole" 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/%C3%81lcool" title="Álcool – Portuguese" lang="pt" hreflang="pt" data-title="Álcool" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ksh mw-list-item"><a href="https://ksh.wikipedia.org/wiki/Alkohol" title="Alkohol – Colognian" lang="ksh" hreflang="ksh" data-title="Alkohol" data-language-autonym="Ripoarisch" data-language-local-name="Colognian" class="interlanguage-link-target"><span>Ripoarisch</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Alcool" title="Alcool – Romanian" lang="ro" hreflang="ro" data-title="Alcool" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Alkul" title="Alkul – Quechua" lang="qu" hreflang="qu" data-title="Alkul" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%BE%D0%B3%D0%BE%D0%BB%D1%8B" title="Алкоголы – Rusyn" lang="rue" hreflang="rue" data-title="Алкоголы" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82%D1%8B" title="Спирты – Russian" lang="ru" hreflang="ru" data-title="Спирты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Alcohol" title="Alcohol – Scots" lang="sco" hreflang="sco" data-title="Alcohol" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Alkooli" title="Alkooli – Albanian" lang="sq" hreflang="sq" data-title="Alkooli" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Alcool" title="Alcool – Sicilian" lang="scn" hreflang="scn" data-title="Alcool" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry) – Simple English" lang="en-simple" hreflang="en-simple" data-title="Alcohol (chemistry)" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Alkohol_(hydroxyderiv%C3%A1t)" title="Alkohol (hydroxyderivát) – Slovak" lang="sk" hreflang="sk" data-title="Alkohol (hydroxyderivát)" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alkohol" title="Alkohol – Slovenian" lang="sl" hreflang="sl" data-title="Alkohol" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D9%84%DA%A9%DA%BE%D9%88%D9%84" title="ئەلکھول – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەلکھول" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%BE%D1%85%D0%BE%D0%BB" title="Алкохол – Serbian" lang="sr" hreflang="sr" data-title="Алкохол" 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/Alkoholi" title="Alkoholi – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Alkoholi" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alkohol" title="Alkohol – Sundanese" lang="su" hreflang="su" data-title="Alkohol" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Alkoholit" title="Alkoholit – Finnish" lang="fi" hreflang="fi" data-title="Alkoholit" 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/Alkoholer" title="Alkoholer – Swedish" lang="sv" hreflang="sv" data-title="Alkoholer" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Alkohol" title="Alkohol – Tagalog" lang="tl" hreflang="tl" data-title="Alkohol" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AE%E0%AE%A4%E0%AF%81%E0%AE%9A%E0%AE%BE%E0%AE%B0%E0%AE%AE%E0%AF%8D" title="மதுசாரம் – Tamil" lang="ta" hreflang="ta" data-title="மதுசாரம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/I%C9%A3isem" title="Iɣisem – Kabyle" lang="kab" hreflang="kab" data-title="Iɣisem" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82%D0%BB%D0%B0%D1%80" title="Спиртлар – Tatar" lang="tt" hreflang="tt" data-title="Спиртлар" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%86%E0%B0%B2%E0%B1%8D%E0%B0%95%E0%B0%B9%E0%B0%BE%E0%B0%B2%E0%B1%81" title="ఆల్కహాలు – Telugu" lang="te" hreflang="te" data-title="ఆల్కహాలు" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%A5%E0%B8%81%E0%B8%AD%E0%B8%AE%E0%B8%AD%E0%B8%A5%E0%B9%8C" title="แอลกอฮอล์ – Thai" lang="th" hreflang="th" data-title="แอลกอฮอล์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alkol" title="Alkol – Turkish" lang="tr" hreflang="tr" data-title="Alkol" 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%A1%D0%BF%D0%B8%D1%80%D1%82%D0%B8" title="Спирти – Ukrainian" lang="uk" hreflang="uk" data-title="Спирти" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%AD%D9%84" title="الکحل – Urdu" lang="ur" hreflang="ur" data-title="الکحل" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Alcohol" title="Alcohol – Vietnamese" lang="vi" hreflang="vi" data-title="Alcohol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%86%87" title="醇 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="醇" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-vls mw-list-item"><a href="https://vls.wikipedia.org/wiki/Alcool" title="Alcool – West Flemish" lang="vls" hreflang="vls" data-title="Alcool" data-language-autonym="West-Vlams" data-language-local-name="West Flemish" class="interlanguage-link-target"><span>West-Vlams</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Arkohol" title="Arkohol – Waray" lang="war" hreflang="war" data-title="Arkohol" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%86%87" title="醇 – Wu" lang="wuu" hreflang="wuu" data-title="醇" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%90%D7%94%D7%90%D7%9C" title="אלקאהאל – Yiddish" lang="yi" hreflang="yi" data-title="אלקאהאל" data-language-autonym="ייִדיש" data-language-local-name="Yiddish" class="interlanguage-link-target"><span>ייִדיש</span></a></li><li class="interlanguage-link interwiki-yo mw-list-item"><a href="https://yo.wikipedia.org/wiki/%E1%BB%8Ct%C3%AD" title="Ọtí – Yoruba" lang="yo" hreflang="yo" data-title="Ọtí" data-language-autonym="Yorùbá" data-language-local-name="Yoruba" class="interlanguage-link-target"><span>Yorùbá</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%85%92%E7%B2%BE" title="酒精 – Cantonese" lang="yue" hreflang="yue" data-title="酒精" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-bat-smg mw-list-item"><a href="https://bat-smg.wikipedia.org/wiki/Alkuoguolis" title="Alkuoguolis – Samogitian" lang="sgs" hreflang="sgs" data-title="Alkuoguolis" data-language-autonym="Žemaitėška" data-language-local-name="Samogitian" class="interlanguage-link-target"><span>Žemaitėška</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%86%87" title="醇 – Chinese" lang="zh" hreflang="zh" data-title="醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li><li class="interlanguage-link interwiki-kge mw-list-item"><a href="https://kge.wikipedia.org/wiki/Alkohol" title="Alkohol – Komering" lang="kge" hreflang="kge" data-title="Alkohol" data-language-autonym="Kumoring" data-language-local-name="Komering" class="interlanguage-link-target"><span>Kumoring</span></a></li> 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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">This article is about the class of chemical compounds. For the alcohol found in alcoholic drinks, see <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (drug)</a>. For other uses, see <a href="/wiki/Alcohol_(disambiguation)" class="mw-redirect mw-disambig" title="Alcohol (disambiguation)">Alcohol (disambiguation)</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Alcohol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Alcohol.png/180px-Alcohol.png" decoding="async" width="180" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Alcohol.png/270px-Alcohol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Alcohol.png/360px-Alcohol.png 2x" data-file-width="1556" data-file-height="1000" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of an alcohol molecule (<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">3</sub>COH</span>). The red and white balls represent the hydroxyl group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>). The three "R"s stand for carbon <a href="/wiki/Substituent" title="Substituent">substituents</a> or hydrogen atoms.<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></figcaption></figure><p> In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, an <b>alcohol</b> (from <a href="/wiki/Arabic_language" class="mw-redirect" title="Arabic language">Arabic</a> <i> al-kuḥl</i> 'the <a href="/wiki/Kohl_(cosmetics)" title="Kohl (cosmetics)">kohl</a>'),<sup id="cite_ref-ScienceFriday_2-0" class="reference"><a href="#cite_note-ScienceFriday-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> is a type of <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> that carries at least one <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>) <a href="/wiki/Functional_group" title="Functional group">functional group</a> bound to a <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated</a> carbon atom.<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><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> Alcohols range from the simple, like <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, to complex, like <a href="/wiki/Sugar" title="Sugar">sugars</a> and <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.<style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style></p><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as <a href="/wiki/Aristotle" title="Aristotle">Aristotle</a> (384–322 BCE), <a href="/wiki/Theophrastus" title="Theophrastus">Theophrastus</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 371</span>–287 BCE), and <a href="/wiki/Pliny_the_Elder" title="Pliny the Elder">Pliny the Elder</a> (23/24–79 CE).<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> However, this did not immediately lead to the isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century <a href="/wiki/Roman_Egypt" title="Roman Egypt">Roman Egypt</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> An important recognition, first found in one of the writings attributed to <a href="/wiki/Jabir_ibn_Hayyan" title="Jabir ibn Hayyan">Jābir ibn Ḥayyān</a> (ninth century CE), was that by <a href="/wiki/Salt-effect_distillation" title="Salt-effect distillation">adding salt</a> to boiling wine, which increases the wine's <a href="/wiki/Relative_volatility" title="Relative volatility">relative volatility</a>, the flammability of the resulting vapors may be enhanced.<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> The distillation of wine is attested in Arabic works attributed to <a href="/wiki/Al-Kindi" title="Al-Kindi">al-Kindī</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 801</span>–873 CE) and to <a href="/wiki/Al-Farabi" title="Al-Farabi">al-Fārābī</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 872</span>–950), and in the 28th book of <a href="/wiki/Al-Zahrawi" title="Al-Zahrawi">al-Zahrāwī</a>'s (Latin: Abulcasis, 936–1013) <i>Kitāb al-Taṣrīf</i> (later translated into Latin as <i>Liber servatoris</i>).<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In the twelfth century, recipes for the production of <i>aqua ardens</i> ("burning water", i.e., alcohol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century, it had become a widely known substance among Western European chemists.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The works of <a href="/wiki/Taddeo_Alderotti" title="Taddeo Alderotti">Taddeo Alderotti</a> (1223–1296) describe a method for concentrating alcohol involving repeated <a href="/wiki/Fractional_distillation" title="Fractional distillation">fractional distillation</a> through a water-cooled still, by which an alcohol purity of 90% could be obtained.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The medicinal properties of ethanol were studied by <a href="/wiki/Arnald_of_Villanova" class="mw-redirect" title="Arnald of Villanova">Arnald of Villanova</a> (1240–1311 CE) and <a href="/wiki/John_of_Rupescissa" class="mw-redirect" title="John of Rupescissa">John of Rupescissa</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 1310</span>–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (the <i><a href="/wiki/Aqua_vitae" title="Aqua vitae">aqua vitae</a></i> or "water of life", also called by John the <i><a href="/wiki/Aether_(classical_element)" title="Aether (classical element)">quintessence</a></i> of wine).<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=2" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=3" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word "alcohol" derives from the Arabic <i><a href="/wiki/Kohl_(cosmetics)" title="Kohl (cosmetics)">kohl</a></i> (<a href="/wiki/Arabic_language" class="mw-redirect" title="Arabic language">Arabic</a>: <span lang="ar" dir="rtl">الكحل</span>, <small><a href="/wiki/Romanization_of_Arabic" title="Romanization of Arabic">romanized</a>: </small><span title="Arabic-language romanization"><i lang="ar-Latn">al-kuḥl</i></span>), a powder used as an eyeliner.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The first part of the word (<span title="Arabic-language romanization"><i lang="ar-Latn"><a href="/wiki/Al-" class="mw-redirect" title="Al-">al-</a></i></span>) is the Arabic <a href="/wiki/Article_(grammar)" title="Article (grammar)">definite article</a>, equivalent to <i>the</i> in English. The second part of the word (<span title="Arabic-language romanization"><i lang="ar-Latn">kuḥl</i></span>) has several antecedents in <a href="/wiki/Semitic_languages" title="Semitic languages">Semitic languages</a>, ultimately deriving from the <a href="/wiki/Akkadian_language" title="Akkadian language">Akkadian</a> <span title="Akkadian-language text"><span lang="akk"><span style="font-size:125%;font-family: lang=">𒎎𒋆𒁉𒍣𒁕</span></span></span> (<span title="Akkadian-language romanization"><i lang="akk-Latn">guḫlum</i></span>), meaning <a href="/wiki/Stibnite" title="Stibnite">stibnite</a> or <a href="/wiki/Antimony" title="Antimony">antimony</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Like its antecedents in Arabic and older languages, the term <i>alcohol</i> was originally used for the very fine powder produced by the <a href="/wiki/Sublimation_(chemistry)" class="mw-redirect" title="Sublimation (chemistry)">sublimation</a> of the natural mineral <a href="/wiki/Stibnite" title="Stibnite">stibnite</a> to form <a href="/wiki/Antimony_trisulfide" title="Antimony trisulfide">antimony trisulfide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sb<sub class="template-chem2-sub">2</sub>S<sub class="template-chem2-sub">3</sub></span>. It was considered to be the essence or "spirit" of this mineral. It was used as an <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a>, eyeliner, and <a href="/wiki/Kohl_(cosmetics)" title="Kohl (cosmetics)">cosmetic</a>. Later the meaning of alcohol was extended to distilled substances in general, and then narrowed again to ethanol, when "spirits" was a synonym for <a href="/wiki/Distilled_beverage" class="mw-redirect" title="Distilled beverage">hard liquor</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Paracelsus" title="Paracelsus">Paracelsus</a> and <a href="/wiki/Libavius" class="mw-redirect" title="Libavius">Libavius</a> both used the term <i>alcohol</i> to denote a fine powder, the latter speaking of an <i>alcohol</i> derived from antimony. At the same time Paracelsus uses the word for a volatile liquid; <i>alcool</i> or <i>alcool vini</i> occurs often in his writings.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Bartholomew_Traheron" title="Bartholomew Traheron">Bartholomew Traheron</a>, in his 1543 translation of <a href="/wiki/John_of_Vigo" class="mw-redirect" title="John of Vigo">John of Vigo</a>, introduces the word as a term used by "barbarous" authors for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre."<sup id="cite_ref-OED-2016_16-0" class="reference"><a href="#cite_note-OED-2016-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The 1657 <i>Lexicon Chymicum</i>, by William Johnson glosses the word as "antimonium sive stibium."<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine," the distilled essence of wine. <a href="/wiki/Libavius" class="mw-redirect" title="Libavius">Libavius</a> in <i>Alchymia</i> (1594) refers to "<style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><span class="rt-commentedText tooltip tooltip-dotted" title="wine alcohol or alkaline wine">vini alcohol vel vinum alcalisatum</span>". Johnson (1657) glosses <i>alcohol vini</i> as "<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><span class="rt-commentedText tooltip tooltip-dotted" title="when all the excess of the wine is separated from the wine, so that the kindling burns until it is all consumed, and no dregs or phlegm remains at the bottom">quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat</span>." The word's meaning became restricted to "spirit of wine" (the chemical known today as <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>) in the 18th century and was extended to the class of substances so-called as "alcohols" in modern chemistry after 1850.<sup id="cite_ref-OED-2016_16-1" class="reference"><a href="#cite_note-OED-2016-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The term <i>ethanol</i> was invented in 1892, <a href="/wiki/Blend_word" title="Blend word">blending</a> "<a href="/wiki/Ethane" title="Ethane">ethane</a>" with the "-ol" ending of "alcohol", which was generalized as a <a href="/wiki/Libfix" title="Libfix">libfix</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>The term <i>alcohol</i> originally referred to the primary alcohol <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> (ethyl alcohol), which is <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">used as a drug</a> and is the <a href="/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">main alcohol present in alcoholic drinks</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Examples_of_Nomenclature_of_Alcohols.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Examples_of_Nomenclature_of_Alcohols.jpg/220px-Examples_of_Nomenclature_of_Alcohols.jpg" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Examples_of_Nomenclature_of_Alcohols.jpg/330px-Examples_of_Nomenclature_of_Alcohols.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Examples_of_Nomenclature_of_Alcohols.jpg/440px-Examples_of_Nomenclature_of_Alcohols.jpg 2x" data-file-width="2185" data-file-height="1209" /></a><figcaption></figcaption></figure> <p>The suffix <i>-ol</i> appears in the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (IUPAC) <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">chemical name</a> of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix <i>hydroxy-</i> is used in its IUPAC name. The suffix <i>-ol</i> in non-IUPAC names (such as <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> or <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>) also typically indicates that the substance is an alcohol. However, some compounds that contain hydroxyl functional groups have <i>trivial names</i> that do not include the suffix <i>-ol</i> or the prefix <i>hydroxy-</i>, e.g. the sugars <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Systematic_names">Systematic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=4" title="Edit section: Systematic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC nomenclature</a> is used in scientific publications, and in writings where precise identification of the substance is important. In naming simple alcohols, the name of the alkane chain loses the terminal <i>e</i> and adds the suffix <i>-ol</i>, <i>e.g.</i>, as in "ethanol" from the alkane chain name "<a href="/wiki/Ethane" title="Ethane">ethane</a>".<sup id="cite_ref-Reusch-2007_19-0" class="reference"><a href="#cite_note-Reusch-2007-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the <i>-ol</i>: <a href="/wiki/Propan-1-ol" class="mw-redirect" title="Propan-1-ol">propan-1-ol</a> for <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH</span>, <a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">propan-2-ol</a> for <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH(OH)CH<sub class="template-chem2-sub">3</sub></span>. If a higher priority group is present (such as an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>, <a href="/wiki/Ketone" title="Ketone">ketone</a>, or <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>), then the prefix <i>hydroxy-</i>is used,<sup id="cite_ref-Reusch-2007_19-1" class="reference"><a href="#cite_note-Reusch-2007-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> e.g., as in <a href="/wiki/1-hydroxy-2-propanone" class="mw-redirect" title="1-hydroxy-2-propanone">1-hydroxy-2-propanone</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)CH<sub class="template-chem2-sub">2</sub>OH</span>).<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Compounds having more than one hydroxy group are called <a href="/wiki/Polyol" title="Polyol">polyols</a>. They are named using suffixes -diol, -triol, etc., following a list of the position numbers of the hydroxyl groups, as in <a href="/wiki/Propylene_glycol" title="Propylene glycol">propane-1,2-diol</a> for CH<sub>3</sub>CH(OH)CH<sub>2</sub>OH (propylene glycol). </p> <table class="wikitable"> <caption>Example alcohols and representations </caption> <tbody><tr> <th><a href="/wiki/Structural_formula" title="Structural formula">Structural formula</a> </th> <th><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> </th> <th><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> </th> <th>Other systematic names </th> <th>Common names </th> <th>Degree </th></tr> <tr style="text-align: center"> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−CH<sub class="template-chem2-sub">2</sub>−CH<sub class="template-chem2-sub">2</sub>−OH</span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Propan-1-ol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Propan-1-ol.svg/100px-Propan-1-ol.svg.png" decoding="async" width="100" height="26" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Propan-1-ol.svg/150px-Propan-1-ol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Propan-1-ol.svg/200px-Propan-1-ol.svg.png 2x" data-file-width="244" data-file-height="64" /></a></span> </td> <td><a href="/wiki/Propan-1-ol" class="mw-redirect" title="Propan-1-ol">propan-1-ol</a> </td> <td>1-propanol;<br /><i>n</i>-propyl alcohol </td> <td>propanol </td> <td>primary </td></tr> <tr style="text-align: center"> <td><span typeof="mw:File"><a href="/wiki/File:Propan-2-ol_displayed.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Propan-2-ol_displayed.svg/85px-Propan-2-ol_displayed.svg.png" decoding="async" width="85" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Propan-2-ol_displayed.svg/128px-Propan-2-ol_displayed.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Propan-2-ol_displayed.svg/170px-Propan-2-ol_displayed.svg.png 2x" data-file-width="120" data-file-height="79" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:2-Propanol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/2-Propanol.svg/60px-2-Propanol.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/2-Propanol.svg/90px-2-Propanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/2-Propanol.svg/120px-2-Propanol.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td> <td><a href="/wiki/Propan-2-ol" class="mw-redirect" title="Propan-2-ol">propan-2-ol</a> </td> <td>2-propanol </td> <td>isopropyl alcohol;<br />isopropanol </td> <td>secondary </td></tr> <tr style="text-align: center"> <td><span typeof="mw:File"><a href="/wiki/File:Cyclohexanol_displayed.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cyclohexanol_displayed.svg/110px-Cyclohexanol_displayed.svg.png" decoding="async" width="110" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cyclohexanol_displayed.svg/165px-Cyclohexanol_displayed.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Cyclohexanol_displayed.svg/220px-Cyclohexanol_displayed.svg.png 2x" data-file-width="167" data-file-height="104" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Cyclohexanol_acsv.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Cyclohexanol_acsv.svg/100px-Cyclohexanol_acsv.svg.png" decoding="async" width="100" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Cyclohexanol_acsv.svg/150px-Cyclohexanol_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Cyclohexanol_acsv.svg/200px-Cyclohexanol_acsv.svg.png 2x" data-file-width="512" data-file-height="365" /></a></span> </td> <td><a href="/wiki/Cyclohexanol" title="Cyclohexanol">cyclohexanol</a> </td> <td>  </td> <td>  </td> <td>secondary </td></tr> <tr style="text-align: center"> <td><span typeof="mw:File"><a href="/wiki/File:2-methylpropan-1-ol_displayed.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/2-methylpropan-1-ol_displayed.svg/100px-2-methylpropan-1-ol_displayed.svg.png" decoding="async" width="100" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/2-methylpropan-1-ol_displayed.svg/150px-2-methylpropan-1-ol_displayed.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/2-methylpropan-1-ol_displayed.svg/200px-2-methylpropan-1-ol_displayed.svg.png 2x" data-file-width="140" data-file-height="79" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isobutanol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Isobutanol.svg/100px-Isobutanol.svg.png" decoding="async" width="100" height="49" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Isobutanol.svg/150px-Isobutanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Isobutanol.svg/200px-Isobutanol.svg.png 2x" data-file-width="775" data-file-height="382" /></a></span> </td> <td><a href="/wiki/2-methylpropan-1-ol" class="mw-redirect" title="2-methylpropan-1-ol">2-methylpropan-1-ol</a> </td> <td>2-methyl-1-propanol </td> <td>isobutyl alcohol;<br />isobutanol </td> <td>primary </td></tr> <tr style="text-align: center"> <td><span typeof="mw:File"><a href="/wiki/File:2-methylbutan-2-ol_displayed.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/2-methylbutan-2-ol_displayed.svg/100px-2-methylbutan-2-ol_displayed.svg.png" decoding="async" width="100" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/2-methylbutan-2-ol_displayed.svg/150px-2-methylbutan-2-ol_displayed.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/2-methylbutan-2-ol_displayed.svg/200px-2-methylbutan-2-ol_displayed.svg.png 2x" data-file-width="216" data-file-height="109" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:2-Methyl-2-butanol_FormulaV1-Seite001.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/2-Methyl-2-butanol_FormulaV1-Seite001.svg/100px-2-Methyl-2-butanol_FormulaV1-Seite001.svg.png" decoding="async" width="100" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/2-Methyl-2-butanol_FormulaV1-Seite001.svg/150px-2-Methyl-2-butanol_FormulaV1-Seite001.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/98/2-Methyl-2-butanol_FormulaV1-Seite001.svg/200px-2-Methyl-2-butanol_FormulaV1-Seite001.svg.png 2x" data-file-width="216" data-file-height="101" /></a></span> </td> <td><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-amyl alcohol</a> </td> <td>2-methylbutan-2-ol;<br />2-methyl-2-butanol </td> <td>TAA </td> <td>tertiary </td></tr></tbody></table> <p>In cases where the hydroxy group is bonded to an sp<sup>2</sup> carbon on an <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic ring</a>, the molecule is classified separately as a <a href="/wiki/Phenols" title="Phenols">phenol</a> and is named using the IUPAC rules for naming phenols.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Phenols" title="Phenols">Phenols</a> have distinct properties and are not classified as alcohols. </p> <div class="mw-heading mw-heading3"><h3 id="Common_names">Common names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=5" title="Edit section: Common names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., <a href="/wiki/Methyl_group" title="Methyl group">methyl</a> alcohol, <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> alcohol. <a href="/wiki/Propyl" class="mw-redirect" title="Propyl">Propyl</a> alcohol may be <a href="/wiki/Propanol" title="Propanol"><i>n</i>-propyl alcohol</a> or <a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">isopropyl alcohol</a>, depending on whether the hydroxyl group is bonded to the end or middle carbon on the straight <a href="/wiki/Propane" title="Propane">propane</a> chain. As described under systematic naming, if another group on the molecule takes priority, the alcohol moiety is often indicated using the "hydroxy-" prefix.<sup id="cite_ref-chem.uiuc_22-0" class="reference"><a href="#cite_note-chem.uiuc-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>In archaic nomenclature, alcohols can be named as derivatives of methanol using "-carbinol" as the ending. For instance, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>COH</span> can be named <a href="/wiki/Trimethylcarbinol" class="mw-redirect" title="Trimethylcarbinol">trimethylcarbinol</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Primary,_secondary,_and_tertiary"><span id="Primary.2C_secondary.2C_and_tertiary"></span>Primary, secondary, and tertiary</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=6" title="Edit section: Primary, secondary, and tertiary"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="anchor" id="secondary"></span><span class="anchor" id="tertiary"></span> Alcohols are then classified into primary, secondary (<i>sec-</i>, <i>s-</i>), and tertiary (<i>tert-</i>, <i>t-</i>), based upon the number of carbon atoms connected to the carbon atom that bears the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a>. The respective numeric shorthands 1°, 2°, and 3° are sometimes used in informal settings.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The primary alcohols have general formulas <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH<sub class="template-chem2-sub">2</sub>OH</span>. The simplest primary alcohol is methanol (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OH</span>), for which R = H, and the next is ethanol, for which <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R = CH<sub class="template-chem2-sub">3</sub></span>, the <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a>. Secondary alcohols are those of the form RR'CHOH, the simplest of which is 2-propanol (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R = R' = CH<sub class="template-chem2-sub">3</sub></span>). For the tertiary alcohols, the general form is RR'R"COH. The simplest example is <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol</a> (2-methylpropan-2-ol), for which each of R, R', and R" is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub></span>. In these shorthands, R, R', and R" represent <a href="/wiki/Substituents" class="mw-redirect" title="Substituents">substituents</a>, alkyl or other attached, generally organic groups. </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=Alcohol_(chemistry)&action=edit&section=7" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Type </th> <th>Formula </th> <th><a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> Name </th> <th>Common name </th></tr> <tr> <td rowspan="6"><i>Monohydric<br />alcohols</i> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OH</span> </td> <td><a href="/wiki/Methanol" title="Methanol">Methanol</a> </td> <td>Wood alcohol </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">5</sub>OH</span> </td> <td><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> </td> <td>Alcohol, Rubbing alcohol </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">7</sub>OH</span> </td> <td><a href="/wiki/Propan-2-ol" class="mw-redirect" title="Propan-2-ol">Propan-2-ol</a> </td> <td>Isopropyl alcohol,<br />Rubbing alcohol </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">9</sub>OH</span> </td> <td><a href="/wiki/Butan-1-ol" class="mw-redirect" title="Butan-1-ol">Butan-1-ol</a> </td> <td>Butanol,<br />Butyl alcohol </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">11</sub>OH</span> </td> <td><a href="/wiki/Pentan-1-ol" class="mw-redirect" title="Pentan-1-ol">Pentan-1-ol</a> </td> <td>Pentanol,<br />Amyl alcohol </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">16</sub>H<sub class="template-chem2-sub">33</sub>OH</span> </td> <td>Hexadecan-1-ol </td> <td><a href="/wiki/Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> </td></tr> <tr> <td rowspan="7"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol"><i>Polyhydric<br />alcohols<br />(sugar<br />alcohols)</i></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>(OH)<sub class="template-chem2-sub">2</sub></span> </td> <td>Ethane-1,2-diol </td> <td><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">6</sub>(OH)<sub class="template-chem2-sub">2</sub></span> </td> <td>Propane-1,2-diol </td> <td><a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>(OH)<sub class="template-chem2-sub">3</sub></span> </td> <td>Propane-1,2,3-triol </td> <td><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">6</sub>(OH)<sub class="template-chem2-sub">4</sub></span> </td> <td>Butane-1,2,3,4-tetraol </td> <td><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a>,<br /><a href="/wiki/Threitol" title="Threitol">Threitol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">7</sub>(OH)<sub class="template-chem2-sub">5</sub></span> </td> <td>Pentane-1,2,3,4,5-pentol </td> <td><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">8</sub>(OH)<sub class="template-chem2-sub">6</sub></span> </td> <td>hexane-1,2,3,4,5,6-hexol </td> <td><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>,<br /><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">9</sub>(OH)<sub class="template-chem2-sub">7</sub></span> </td> <td>Heptane-1,2,3,4,5,6,7-heptol </td> <td><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> </td></tr> <tr> <td rowspan="3"><i>Unsaturated<br /><a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> alcohols</i> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>OH</span> </td> <td>Prop-2-ene-1-ol </td> <td><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">17</sub>OH</span> </td> <td>3,7-Dimethylocta-2,6-dien-1-ol </td> <td><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">3</sub>OH</span> </td> <td>Prop-2-yn-1-ol </td> <td><a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">Propargyl alcohol</a> </td></tr> <tr> <td rowspan="2"><i><a href="/wiki/Alicyclic" class="mw-redirect" title="Alicyclic">Alicyclic</a> alcohols</i> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub>(OH)<sub class="template-chem2-sub">6</sub></span> </td> <td>Cyclohexane-1,2,3,4,5,6-hexol </td> <td><a href="/wiki/Inositol" title="Inositol">Inositol</a> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">19</sub>OH</span> </td> <td>5-Methyl-2-(propan-2-yl)cyclohexan-1-ol </td> <td><a href="/wiki/Menthol" title="Menthol">Menthol</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=8" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Alcohol_by_Country.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/200px-Alcohol_by_Country.png" decoding="async" width="200" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/300px-Alcohol_by_Country.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/400px-Alcohol_by_Country.png 2x" data-file-width="1800" data-file-height="820" /></a><figcaption>Total recorded <a href="/wiki/Alcohol_consumption_by_country" class="mw-redirect" title="Alcohol consumption by country">alcohol per capita consumption</a> (15+) per year, in litres of pure ethanol<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Alcohols have a long history of myriad uses. For simple mono-alcohols, which is the focus on this article, the following are most important industrial alcohols:<sup id="cite_ref-Falbe_25-0" class="reference"><a href="#cite_note-Falbe-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <ul><li>methanol, mainly for the production of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and as a <a href="/wiki/Fuel_additive" class="mw-redirect" title="Fuel additive">fuel additive</a></li> <li>ethanol, mainly for alcoholic beverages, fuel additive, solvent, and to sterilize hospital instruments.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li>1-propanol, 1-butanol, and isobutyl alcohol for use as a solvent and precursor to solvents</li> <li>C6–C11 alcohols used for <a href="/wiki/Plasticizer" title="Plasticizer">plasticizers</a>, e.g. in <a href="/wiki/Polyvinylchloride" class="mw-redirect" title="Polyvinylchloride">polyvinylchloride</a></li> <li>fatty alcohol (C12–C18), precursors to <a href="/wiki/Detergent" title="Detergent">detergents</a></li></ul> <p>Methanol is the most common industrial alcohol, with about 12 million tons/y produced in 1980. The combined capacity of the other alcohols is about the same, distributed roughly equally.<sup id="cite_ref-Falbe_25-1" class="reference"><a href="#cite_note-Falbe-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=9" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>With respect to acute toxicity, simple alcohols have low acute <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxicities</a>. Doses of several milliliters are tolerated. For <a href="/wiki/Pentanol" class="mw-redirect" title="Pentanol">pentanols</a>, <a href="/wiki/Hexanol" title="Hexanol">hexanols</a>, <a href="/wiki/Octanol" title="Octanol">octanols</a>, and longer alcohols, <a href="/wiki/LD50" class="mw-redirect" title="LD50">LD50</a> range from 2–5 g/kg (rats, oral). Ethanol is less acutely toxic.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> All alcohols are mild skin irritants.<sup id="cite_ref-Falbe_25-2" class="reference"><a href="#cite_note-Falbe-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Methanol and ethylene glycol are more toxic than other simple alcohols. Their metabolism is affected by the presence of ethanol, which has a higher affinity for <a href="/wiki/Liver_alcohol_dehydrogenase" class="mw-redirect" title="Liver alcohol dehydrogenase">liver alcohol dehydrogenase</a>. In this way, <a href="/wiki/Methanol" title="Methanol">methanol</a> will be excreted intact in urine.<sup id="cite_ref-Schep-2009_28-0" class="reference"><a href="#cite_note-Schep-2009-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=10" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> makes alcohols <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar</a>. Those groups can form <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> to one another and to most other compounds. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> in water. <a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a>, with a four-carbon chain, is moderately soluble. </p><p>Because of <a href="/wiki/Hydrogen_bonding" class="mw-redirect" title="Hydrogen bonding">hydrogen bonding</a>, alcohols tend to have higher boiling points than comparable <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> and <a href="/wiki/Ether" title="Ether">ethers</a>. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon <a href="/wiki/Hexane" title="Hexane">hexane</a>, and 34.6 °C for <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_in_nature">Occurrence in nature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=11" title="Edit section: Occurrence in nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alcohols occur widely in nature, as derivatives of <a href="/wiki/Glucose" title="Glucose">glucose</a> such as <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> and <a href="/wiki/Hemicellulose" title="Hemicellulose">hemicellulose</a>, and in <a href="/wiki/Phenols" title="Phenols">phenols</a> and their derivatives such as <a href="/wiki/Lignin" title="Lignin">lignin</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Starting from <a href="/wiki/Biomass" title="Biomass">biomass</a>, 180 billion tons/y of complex carbohydrates (sugar polymers) are produced commercially (as of 2014).<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Many other alcohols are pervasive in organisms, as manifested in other sugars such as <a href="/wiki/Fructose" title="Fructose">fructose</a> and <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, in polyols such as <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>, and in some <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> such as <a href="/wiki/Serine" title="Serine">serine</a>. Simple alcohols like methanol, ethanol, and propanol occur in modest quantities in nature, and are industrially synthesized in large quantities for use as chemical precursors, fuels, and solvents. </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=12" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Hydroxylation">Hydroxylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=13" title="Edit section: Hydroxylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many alcohols are produced by <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, i.e., the installation of a hydroxy group using oxygen or a related oxidant. Hydroxylation is the means by which the body processes many <a href="/wiki/Xenobiotic" title="Xenobiotic">poisons</a>, converting lipophilic compounds into hydrophilic derivatives that are more readily excreted. Enzymes called <a href="/wiki/Hydroxylase" class="mw-redirect" title="Hydroxylase">hydroxylases</a> and <a href="/wiki/Oxidase" title="Oxidase">oxidases</a> facilitate these conversions. </p><p>Many industrial alcohols, such as <a href="/wiki/Cyclohexanol" title="Cyclohexanol">cyclohexanol</a> for the production of <a href="/wiki/Nylon" title="Nylon">nylon</a>, are produced by hydroxylation. </p> <div class="mw-heading mw-heading3"><h3 id="Ziegler_and_oxo_processes">Ziegler and oxo processes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=14" title="Edit section: Ziegler and oxo processes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Ziegler_process" title="Ziegler process">Ziegler process</a>, linear alcohols are produced from ethylene and <a href="/wiki/Triethylaluminium" title="Triethylaluminium">triethylaluminium</a> followed by oxidation and hydrolysis.<sup id="cite_ref-Falbe_25-3" class="reference"><a href="#cite_note-Falbe-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> An idealized synthesis of <a href="/wiki/1-octanol" class="mw-redirect" title="1-octanol">1-octanol</a> is shown: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Al(C2H5)3 + 9 C2H4 -> Al(C8H17)3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Al</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>9</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>Al</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>8</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>17</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Al(C2H5)3 + 9 C2H4 -> Al(C8H17)3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d9b6552f7841a81d1cb73bfd9858d56b558eb282" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:37.404ex; height:3.009ex;" alt="{\displaystyle {\ce {Al(C2H5)3 + 9 C2H4 -> Al(C8H17)3}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Al(C8H17)3 + 3O + 3 H2O -> 3 HOC8H17 + Al(OH)3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Al</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>8</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>17</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>3</mn> <mspace width="thinmathspace" /> <mtext>O</mtext> <mo>+</mo> <mn>3</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <mn>3</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>HOC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>8</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>17</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mtext>Al</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Al(C8H17)3 + 3O + 3 H2O -> 3 HOC8H17 + Al(OH)3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/90449a52abf76a7546b88781f11d7e8be54b9d98" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:54.992ex; height:3.009ex;" alt="{\displaystyle {\ce {Al(C8H17)3 + 3O + 3 H2O -> 3 HOC8H17 + Al(OH)3}}}"></span></dd></dl> <p>The process generates a range of alcohols that are separated by <a href="/wiki/Distillation" title="Distillation">distillation</a>. </p><p>Many higher alcohols are produced by <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> of alkenes followed by hydrogenation. When applied to a <a href="/wiki/Terminal_alkene" title="Terminal alkene">terminal alkene</a>, as is common, one typically obtains a linear alcohol:<sup id="cite_ref-Falbe_25-4" class="reference"><a href="#cite_note-Falbe-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCH=CH2 + H2 + CO -> RCH2CH2CHO}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mtext>CO</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CHO</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCH=CH2 + H2 + CO -> RCH2CH2CHO}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/3e85e9b045e3e2e12e0ba2c0cb71574dca9d3bdf" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:44.366ex; height:2.843ex;" alt="{\displaystyle {\ce {RCH=CH2 + H2 + CO -> RCH2CH2CHO}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCH2CH2CHO + 3 H2 -> RCH2CH2CH2OH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CHO</mtext> <mo>+</mo> <mn>3</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>OH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCH2CH2CHO + 3 H2 -> RCH2CH2CH2OH}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e943848f9950994e20829f758793840fe0c8fcf1" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:46.862ex; height:2.843ex;" alt="{\displaystyle {\ce {RCH2CH2CHO + 3 H2 -> RCH2CH2CH2OH}}}"></span></dd></dl> <p>Such processes give <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a>, which are useful for detergents. </p> <div class="mw-heading mw-heading3"><h3 id="Hydration_reactions">Hydration reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=15" title="Edit section: Hydration reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and <i>tert</i>-butanol are produced by this general method. Two implementations are employed, the direct and indirect methods. The direct method avoids the formation of stable intermediates, typically using acid catalysts. In the indirect method, the alkene is converted to the <a href="/wiki/Sulfate_ester" class="mw-redirect" title="Sulfate ester">sulfate ester</a>, which is subsequently hydrolyzed. The direct <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> uses <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (<a href="/wiki/Ethanol#Hydration" title="Ethanol">ethylene hydration</a>)<sup id="cite_ref-Lodgsdon-1994_33-0" class="reference"><a href="#cite_note-Lodgsdon-1994-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> or other alkenes from <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> of fractions of distilled <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">crude oil</a>. </p><p>Hydration is also used industrially to produce the diol <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> from <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Fermentation">Fermentation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=16" title="Edit section: Fermentation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethanol is obtained by <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> of <a href="/wiki/Glucose" title="Glucose">glucose</a> (which is often obtained from <a href="/wiki/Starch" title="Starch">starch</a>) in the presence of yeast. Carbon dioxide is cogenerated. Like ethanol, <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a> can be produced by fermentation processes. <i>Saccharomyces</i> yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). The bacterium <i><a href="/wiki/Clostridium_acetobutylicum" title="Clostridium acetobutylicum">Clostridium acetobutylicum</a></i> can feed on <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> (also an alcohol) to produce butanol on an industrial scale.<sup id="cite_ref-Zverlov-2006_34-0" class="reference"><a href="#cite_note-Zverlov-2006-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Substitution">Substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=17" title="Edit section: Substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Primary <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a> react with aqueous <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">NaOH</a> or <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">KOH</a> to give alcohols in <a href="/wiki/Nucleophilic_aliphatic_substitution" class="mw-redirect" title="Nucleophilic aliphatic substitution">nucleophilic aliphatic substitution</a>. Secondary and especially tertiary alkyl halides will give the elimination (alkene) product instead. <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a> react with <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> groups to give secondary and tertiary alcohols. Related reactions are the <a href="/wiki/Barbier_reaction" title="Barbier reaction">Barbier reaction</a> and the <a href="/wiki/Nozaki-Hiyama_reaction" class="mw-redirect" title="Nozaki-Hiyama reaction">Nozaki-Hiyama reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=18" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">Aldehydes</a> or <a href="/wiki/Ketone" title="Ketone">ketones</a> are <a href="/wiki/Redox" title="Redox">reduced</a> with <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a> or <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a> (after an acidic workup). Another reduction using <a href="/wiki/Aluminium_isopropoxide" title="Aluminium isopropoxide">aluminium isopropoxide</a> is the <a href="/wiki/Meerwein-Ponndorf-Verley_reduction" class="mw-redirect" title="Meerwein-Ponndorf-Verley reduction">Meerwein-Ponndorf-Verley reduction</a>. <a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a> is the asymmetric reduction of β-keto-esters. </p> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=19" title="Edit section: Hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">Alkenes</a> engage in an acid catalyzed <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration reaction</a> using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. Formation of a secondary alcohol via <a href="/wiki/Hydration_reaction#Alkenes" title="Hydration reaction">alkene reduction and hydration</a> is shown: </p> <dl><dd><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Secondary_alcohol_formation-diagram.svg" class="mw-file-description" title="Preparation of a secondary alcohol"><img alt="Preparation of a secondary alcohol" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Secondary_alcohol_formation-diagram.svg/350px-Secondary_alcohol_formation-diagram.svg.png" decoding="async" width="350" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Secondary_alcohol_formation-diagram.svg/525px-Secondary_alcohol_formation-diagram.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Secondary_alcohol_formation-diagram.svg/700px-Secondary_alcohol_formation-diagram.svg.png 2x" data-file-width="566" data-file-height="96" /></a></span></dd></dl> <p>The <a href="/wiki/Hydroboration-oxidation" class="mw-redirect" title="Hydroboration-oxidation">hydroboration-oxidation</a> and <a href="/wiki/Oxymercuration-reduction" class="mw-redirect" title="Oxymercuration-reduction">oxymercuration-reduction</a> of alkenes are more reliable in organic synthesis. Alkenes react with <a href="/wiki/N-Bromosuccinimide" title="N-Bromosuccinimide"><i>N</i>-bromosuccinimide</a> and water in <a href="/wiki/Halohydrin_formation_reaction" class="mw-redirect" title="Halohydrin formation reaction">halohydrin formation reaction</a>. <a href="/wiki/Amine" title="Amine">Amines</a> can be converted to <a href="/wiki/Diazonium_salt" class="mw-redirect" title="Diazonium salt">diazonium salts</a>, which are then hydrolyzed. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=20" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Deprotonation">Deprotonation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=21" title="Edit section: Deprotonation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>With aqueous <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> values of around 16–19, alcohols are, in general, slightly weaker <a href="/wiki/Acid" title="Acid">acids</a> than <a href="/wiki/Water" title="Water">water</a>. With strong bases such as <a href="/wiki/Sodium_hydride" title="Sodium hydride">sodium hydride</a> or <a href="/wiki/Sodium" title="Sodium">sodium</a> they form <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> called <i><a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a></i>, with the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO<sup class="template-chem2-sup">−</sup>M<sup class="template-chem2-sup">+</sup></span> (where R is an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> and M is a <a href="/wiki/Metal" title="Metal">metal</a>). </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 R-OH + 2 NaH -> 2 R-O-Na + 2 H2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>NaH</mtext> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Na</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 R-OH + 2 NaH -> 2 R-O-Na + 2 H2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/9705883f5eb63d0f8601cd834de8f1060eeae381" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.531ex; height:2.843ex;" alt="{\displaystyle {\ce {2 R-OH + 2 NaH -> 2 R-O-Na + 2 H2}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 R-OH + 2 Na -> 2 R-O-Na + H2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>Na</mtext> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Na</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 R-OH + 2 Na -> 2 R-O-Na + H2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2451b44e60f7cc40fe7ee8f8843691c47f2f4334" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:38.239ex; height:2.843ex;" alt="{\displaystyle {\ce {2 R-OH + 2 Na -> 2 R-O-Na + H2}}}"></span></dd></dl> <p>The acidity of alcohols is strongly affected by <a href="/wiki/Solvation" title="Solvation">solvation</a>. In the gas phase, alcohols are more acidic than in water.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/DMSO" class="mw-redirect" title="DMSO">DMSO</a>, alcohols (and water) have a p<i>K</i><sub>a</sub> of around 29–32. As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the <a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a>) in this solvent. In particular, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO<sup class="template-chem2-sup">−</sup></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HO<sup class="template-chem2-sup">−</sup></span> in DMSO can be used to generate significant equilibrium concentrations of acetylide ions through the deprotonation of alkynes (see <a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a>).<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_substitution">Nucleophilic substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=22" title="Edit section: Nucleophilic substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tertiary alcohols react with <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> to produce tertiary <a href="/wiki/Alkyl_chloride" class="mw-redirect" title="Alkyl chloride">alkyl chloride</a>. Primary and secondary alcohols are converted to the corresponding chlorides using <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a> and various phosphorus chloride reagents.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Alcohol_reaction_examples.svg" class="mw-file-description" title="Some simple conversions of alcohols to alkyl chlorides"><img alt="Some simple conversions of alcohols to alkyl chlorides" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Alcohol_reaction_examples.svg/700px-Alcohol_reaction_examples.svg.png" decoding="async" width="700" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Alcohol_reaction_examples.svg/1050px-Alcohol_reaction_examples.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/Alcohol_reaction_examples.svg/1400px-Alcohol_reaction_examples.svg.png 2x" data-file-width="606" data-file-height="55" /></a></span> </p><p>Primary and secondary alcohols, likewise, convert to <a href="/wiki/Alkyl_bromide" class="mw-redirect" title="Alkyl bromide">alkyl bromides</a> using <a href="/wiki/Phosphorus_tribromide" title="Phosphorus tribromide">phosphorus tribromide</a>, for example: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {3 R-OH + PBr3 -> 3 RBr + H3PO3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> <mspace width="thinmathspace" /> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <msubsup> <mtext>PBr</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mn>3</mn> <mspace width="thinmathspace" /> <mtext>RBr</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>PO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {3 R-OH + PBr3 -> 3 RBr + H3PO3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/fe0e13bdb30ff904fb5411fec6097ed1b9bc2369" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:37.65ex; height:2.843ex;" alt="{\displaystyle {\ce {3 R-OH + PBr3 -> 3 RBr + H3PO3}}}"></span></dd></dl> <p>In the <a href="/wiki/Barton-McCombie_deoxygenation" class="mw-redirect" title="Barton-McCombie deoxygenation">Barton-McCombie deoxygenation</a> an alcohol is deoxygenated to an <a href="/wiki/Alkane" title="Alkane">alkane</a> with <a href="/wiki/Tributyltin_hydride" title="Tributyltin hydride">tributyltin hydride</a> or a <a href="/wiki/Organoborane" class="mw-redirect" title="Organoborane">trimethylborane</a>-water complex in a <a href="/wiki/Radical_substitution" title="Radical substitution">radical substitution</a> reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Dehydration">Dehydration</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=23" title="Edit section: Dehydration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Meanwhile, the oxygen atom has <a href="/wiki/Lone_pair" title="Lone pair">lone pairs</a> of nonbonded electrons that render it weakly <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> in the presence of strong acids such as <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>. For example, with methanol: </p><p><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Methanol_acid_base.svg" class="mw-file-description" title="Acidity & basicity of methanol"><img alt="Acidity & basicity of methanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Methanol_acid_base.svg/500px-Methanol_acid_base.svg.png" decoding="async" width="500" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Methanol_acid_base.svg/750px-Methanol_acid_base.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Methanol_acid_base.svg/1000px-Methanol_acid_base.svg.png 2x" data-file-width="512" data-file-height="95" /></a></span> </p><p>Upon treatment with strong acids, alcohols undergo the E1 <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reaction</a> to produce <a href="/wiki/Alkene" title="Alkene">alkenes</a>. The reaction, in general, obeys <a href="/wiki/Zaitsev%27s_Rule" class="mw-redirect" title="Zaitsev's Rule">Zaitsev's Rule</a>, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols are eliminated easily at just above room temperature, but primary alcohols require a higher temperature. </p><p>This is a diagram of acid catalyzed dehydration of ethanol to produce <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>: </p><p><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:DehydrationOfAlcoholWithH-.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/DehydrationOfAlcoholWithH-.png/550px-DehydrationOfAlcoholWithH-.png" decoding="async" width="550" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/DehydrationOfAlcoholWithH-.png/825px-DehydrationOfAlcoholWithH-.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/DehydrationOfAlcoholWithH-.png/1100px-DehydrationOfAlcoholWithH-.png 2x" data-file-width="1500" data-file-height="225" /></a></span> </p><p>A more controlled elimination reaction requires the formation of the <a href="/w/index.php?title=Xanthate_ester&action=edit&redlink=1" class="new" title="Xanthate ester (page does not exist)">xanthate ester</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Protonolysis">Protonolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=24" title="Edit section: Protonolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tertiary alcohols react with strong acids to generate carbocations. The reaction is related to their dehydration, e.g. <a href="/wiki/Isobutylene" title="Isobutylene">isobutylene</a> from <i>tert</i>-butyl alcohol. A special kind of dehydration reaction involves <a href="/wiki/Triphenylmethanol" title="Triphenylmethanol">triphenylmethanol</a> and especially its amine-substituted derivatives. When treated with acid, these alcohols lose water to give stable carbocations, which are commercial dyes.<sup id="cite_ref-Gessner-2000_40-0" class="reference"><a href="#cite_note-Gessner-2000-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Kristallviolett_Darstellung.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Kristallviolett_Darstellung.svg/322px-Kristallviolett_Darstellung.svg.png" decoding="async" width="322" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Kristallviolett_Darstellung.svg/483px-Kristallviolett_Darstellung.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Kristallviolett_Darstellung.svg/644px-Kristallviolett_Darstellung.svg.png 2x" data-file-width="894" data-file-height="257" /></a><figcaption>Preparation of <a href="/wiki/Crystal_violet" title="Crystal violet">crystal violet</a> by protonolysis of the tertiary alcohol.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Esterification">Esterification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=25" title="Edit section: Esterification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alcohol and <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> react in the so-called <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a>. The reaction usually requires a <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, such as concentrated sulfuric acid: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R-OH + R'-CO2H -> R'-CO2R + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>H</mtext> <mo stretchy="false">⟶</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>R</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R-OH + R'-CO2H -> R'-CO2R + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/92e5266ee6ca8d5900ba7ff27adb0cdb0a940cb6" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:43.394ex; height:3.176ex;" alt="{\displaystyle {\ce {R-OH + R'-CO2H -> R'-CO2R + H2O}}}"></span></dd></dl> <p>Other types of ester are prepared in a similar manner−for example, <a href="/wiki/Tosyl" class="mw-redirect" title="Tosyl">tosyl</a> (tosylate) esters are made by reaction of the alcohol with <a href="/wiki/4-toluenesulfonyl_chloride" class="mw-redirect" title="4-toluenesulfonyl chloride">4-toluenesulfonyl chloride</a> in <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=26" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a></div> <p>Primary alcohols (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH<sub class="template-chem2-sub">2</sub>OH</span>) can be oxidized either to <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CHO</span>) or to <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CO<sub class="template-chem2-sub">2</sub>H</span>). The oxidation of secondary alcohols (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>R<sup class="template-chem2-sup">2</sup>CH−OH</span>) normally terminates at the <a href="/wiki/Ketone" title="Ketone">ketone</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>R<sup class="template-chem2-sup">2</sup>C=O</span>) stage. Tertiary alcohols (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>R<sup class="template-chem2-sup">2</sup>R<sup class="template-chem2-sup">3</sup>C−OH</span>) are resistant to oxidation. </p><p>The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an <i>aldehyde hydrate</i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH(OH)<sub class="template-chem2-sub">2</sub></span>) by reaction with water before it can be further oxidized to the carboxylic acid. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Alcohol_to_aldehyde_to_acid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Alcohol_to_aldehyde_to_acid.png/500px-Alcohol_to_aldehyde_to_acid.png" decoding="async" width="500" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Alcohol_to_aldehyde_to_acid.png/750px-Alcohol_to_aldehyde_to_acid.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Alcohol_to_aldehyde_to_acid.png/1000px-Alcohol_to_aldehyde_to_acid.png 2x" data-file-width="1474" data-file-height="230" /></a><figcaption>Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates</figcaption></figure> <p>Reagents useful for the transformation of primary alcohols to aldehydes are normally also suitable for the oxidation of secondary alcohols to ketones. These include <a href="/wiki/Collins_reagent" title="Collins reagent">Collins reagent</a> and <a href="/wiki/Dess-Martin_periodinane" class="mw-redirect" title="Dess-Martin periodinane">Dess-Martin periodinane</a>. The direct oxidation of primary alcohols to carboxylic acids can be carried out using <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a> or the <a href="/wiki/Jones_reagent" class="mw-redirect" title="Jones reagent">Jones reagent</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=Alcohol_(chemistry)&action=edit&section=27" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 20em;"> <ul><li><a href="/wiki/Beer_chemistry" title="Beer chemistry">Beer chemistry</a></li> <li><a href="/wiki/Enol" title="Enol">Enol</a></li> <li><a href="/wiki/Ethanol_fuel" title="Ethanol fuel">Ethanol fuel</a></li> <li><a href="/wiki/Fatty_alcohol" title="Fatty alcohol">Fatty alcohol</a></li> <li><a href="/wiki/Index_of_alcohol-related_articles" title="Index of alcohol-related articles">Index of alcohol-related articles</a></li> <li><a href="/wiki/List_of_alcohols" class="mw-redirect" title="List of alcohols">List of alcohols</a></li> <li><a href="/wiki/Lucas%27_reagent" title="Lucas' reagent">Lucas test</a></li> <li><a href="/wiki/Polyol" title="Polyol">Polyol</a></li> <li><a href="/wiki/Rubbing_alcohol" title="Rubbing alcohol">Rubbing alcohol</a></li> <li><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohol</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li> <li><a href="/wiki/Wine_chemistry" title="Wine chemistry">Wine chemistry</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=28" title="Edit section: Notes"><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 reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text">Although commonly described as "salts", alkali metal alkoxides are actually better described structurally as oligomeric clusters or polymeric chains. For instance, potassium <i>tert</i>-butoxide consists of a cubane-like tetramer, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[<i>t</i>-BuOK]<sub class="template-chem2-sub">4</sub></span>, that persists even in polar solvents like THF.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Citations">Citations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=29" title="Edit section: Citations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <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 class="citation journal cs1"><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/A00204.html">"alcohols"</a>. <i>IUPAC Gold Book</i>. 2014. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00204">10.1351/goldbook.A00204</a></span><span class="reference-accessdate">. Retrieved <span class="nowrap">16 December</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=IUPAC+Gold+Book&rft.atitle=alcohols&rft.date=2014&rft_id=info%3Adoi%2F10.1351%2Fgoldbook.A00204&rft_id=http%3A%2F%2Fgoldbook.iupac.org%2FA00204.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></span> </li> <li id="cite_note-ScienceFriday-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-ScienceFriday_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sciencefriday.com/articles/the-origin-of-the-word-alcohol/">"The Origin Of The Word 'Alcohol'<span class="cs1-kern-right"></span>"</a>. <i>Science Friday</i><span class="reference-accessdate">. Retrieved <span class="nowrap">30 September</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Science+Friday&rft.atitle=The+Origin+Of+The+Word+%27Alcohol%27&rft_id=https%3A%2F%2Fwww.sciencefriday.com%2Farticles%2Fthe-origin-of-the-word-alcohol%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><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/A00204.html">Alcohols</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.A00204">10.1351/goldbook.A00204</a></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="CITEREFSaul_Patai1971" class="citation book cs1">Saul Patai, ed. (1971). <i>The Hydroxyl Group</i>. PATAI'S Chemistry of Functional Groups. <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%2F9780470771259">10.1002/9780470771259</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77125-9" title="Special:BookSources/978-0-470-77125-9"><bdi>978-0-470-77125-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Hydroxyl+Group&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.date=1971&rft_id=info%3Adoi%2F10.1002%2F9780470771259&rft.isbn=978-0-470-77125-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerthelotHoudas1893" class="citation book cs1 cs1-prop-long-vol"><a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Berthelot M</a>, Houdas OV (1893). <i>La Chimie au Moyen Âge</i>. Vol. I–III. Paris: Imprimerie nationale.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=La+Chimie+au+Moyen+%C3%82ge&rft.place=Paris&rft.pub=Imprimerie+nationale&rft.date=1893&rft.aulast=Berthelot&rft.aufirst=Marcellin&rft.au=Houdas%2C+Octave+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span> vol. I, p. 137.</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"><a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, pp. 138–139.</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="CITEREFal-Hassan2009" class="citation book cs1"><a href="/wiki/Ahmad_Y._al-Hassan" title="Ahmad Y. al-Hassan">al-Hassan AY</a> (2009). "Alcohol and the Distillation of Wine in Arabic Sources from the 8th Century". <i>Studies in al-Kimya': Critical Issues in Latin and Arabic Alchemy and Chemistry</i>. Hildesheim: Georg Olms Verlag. pp. 283–298.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alcohol+and+the+Distillation+of+Wine+in+Arabic+Sources+from+the+8th+Century&rft.btitle=Studies+in+al-Kimya%27%3A+Critical+Issues+in+Latin+and+Arabic+Alchemy+and+Chemistry&rft.place=Hildesheim&rft.pages=283-298&rft.pub=Georg+Olms+Verlag&rft.date=2009&rft.aulast=al-Hassan&rft.aufirst=Ahmad+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span> (same content also available on <a rel="nofollow" class="external text" href="http://www.history-science-technology.com/notes/notes7.html">the author's website</a>).</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><a href="#CITEREFal-Hassan2009">al-Hassan 2009</a> (same content also available on <a rel="nofollow" class="external text" href="http://www.history-science-technology.com/notes/notes7.html">the author's website</a>); cf. <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, pp. 141, 143. Sometimes, sulfur was also added to the wine (see <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, p. 143).</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMulthauf1966" class="citation book cs1"><a href="/wiki/Robert_P._Multhauf" title="Robert P. Multhauf">Multhauf RP</a> (1966). <i>The Origins of Chemistry</i>. London: Oldbourne. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-2-88124-594-7" title="Special:BookSources/978-2-88124-594-7"><bdi>978-2-88124-594-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Origins+of+Chemistry&rft.place=London&rft.pub=Oldbourne&rft.date=1966&rft.isbn=978-2-88124-594-7&rft.aulast=Multhauf&rft.aufirst=Robert+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span> pp. 204–206.</span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHolmyard1957" class="citation book cs1"><a href="/wiki/Eric_John_Holmyard" title="Eric John Holmyard">Holmyard EJ</a> (1957). <i>Alchemy</i>. Harmondsworth: Penguin Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-486-26298-7" title="Special:BookSources/978-0-486-26298-7"><bdi>978-0-486-26298-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Alchemy&rft.place=Harmondsworth&rft.pub=Penguin+Books&rft.date=1957&rft.isbn=978-0-486-26298-7&rft.aulast=Holmyard&rft.aufirst=Eric+John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span> pp. 51–52.</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrincipe2013" class="citation book cs1"><a href="/wiki/Lawrence_M._Principe" title="Lawrence M. Principe">Principe LM</a> (2013). <i>The Secrets of Alchemy</i>. 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PATai's Chemistry of Functional Groups. pp. 593–639. <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%2F9780470771259.ch11">10.1002/9780470771259.ch11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-77125-9" title="Special:BookSources/978-0-470-77125-9"><bdi>978-0-470-77125-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Displacement+of+Hydroxyl+Groups&rft.btitle=The+Hydroxyl+Group+%281971%29&rft.series=PATai%27s+Chemistry+of+Functional+Groups&rft.pages=593-639&rft.date=1971&rft_id=info%3Adoi%2F10.1002%2F9780470771259.ch11&rft.isbn=978-0-470-77125-9&rft.aulast=Brown&rft.aufirst=Geoffrey+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></span> </li> <li id="cite_note-Gessner-2000-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gessner-2000_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGessnerMayer2000" class="citation encyclopaedia cs1">Gessner T, Mayer U (2000). "Triarylmethane and Diarylmethane Dyes". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <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.a27_179">10.1002/14356007.a27_179</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Triarylmethane+and+Diarylmethane+Dyes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a27_179&rft.isbn=978-3527306732&rft.aulast=Gessner&rft.aufirst=Thomas&rft.au=Mayer%2C+Udo&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="General_references">General references</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alcohol_(chemistry)&action=edit&section=30" title="Edit section: General references"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMetcalf1999" class="citation book cs1">Metcalf AA (1999). <i>The World in So Many Words</i>. Houghton Mifflin. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-395-95920-9" title="Special:BookSources/0-395-95920-9"><bdi>0-395-95920-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+World+in+So+Many+Words&rft.pub=Houghton+Mifflin&rft.date=1999&rft.isbn=0-395-95920-9&rft.aulast=Metcalf&rft.aufirst=Allan+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlcohol+%28chemistry%29" class="Z3988"></span></li></ul> <style data-mw-deduplicate="TemplateStyles:r1236088147">.mw-parser-output .sister-bar{display:flex;justify-content:center;align-items:baseline;font-size:88%;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em 0 0;padding:0 2em}.mw-parser-output .sister-bar-header{margin:0 1em 0 0.5em;padding:0.2em 0;flex:0 0 auto;min-height:24px;line-height:22px}.mw-parser-output .sister-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;align-items:baseline;padding:0.2em 0;column-gap:1em;margin:0;list-style:none}.mw-parser-output .sister-bar-item{display:flex;align-items:baseline;margin:0.15em 0;min-height:24px;text-align:left}.mw-parser-output .sister-bar-logo{width:22px;line-height:22px;margin:0 0.2em;text-align:right}.mw-parser-output .sister-bar-link{margin:0 0.2em;text-align:left}@media screen and (max-width:960px){.mw-parser-output .sister-bar{flex-flow:column wrap;margin:1em auto 0}.mw-parser-output .sister-bar-header{flex:0 1}.mw-parser-output .sister-bar-content{flex:1;border-top:1px solid #a2a9b1;margin:0;list-style:none}.mw-parser-output .sister-bar-item{flex:0 0 20em;min-width:20em}}.mw-parser-output .navbox+link+.sister-bar,.mw-parser-output .navbox+style+.sister-bar,.mw-parser-output .portal-bar+link+.sister-bar,.mw-parser-output .portal-bar+style+.sister-bar,.mw-parser-output .sister-bar+.navbox-styles+.navbox,.mw-parser-output .sister-bar+.navbox-styles+.portal-bar{margin-top:-1px}@media print{body.ns-0 .mw-parser-output .sister-bar{display:none!important}}</style><div class="noprint metadata sister-bar" role="navigation" aria-label="sister-projects"><div class="sister-bar-header"><b>Alcohol</b> at Wikipedia's <a href="/wiki/Wikipedia:Wikimedia_sister_projects" title="Wikipedia:Wikimedia sister projects"><span id="sister-projects" style="white-space:nowrap;">sister projects</span></a>:</div><ul class="sister-bar-content"><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/19px-Wiktionary-logo-v2.svg.png" decoding="async" width="19" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/29px-Wiktionary-logo-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/0/06/Wiktionary-logo-v2.svg/38px-Wiktionary-logo-v2.svg.png 2x" data-file-width="391" data-file-height="391" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wiktionary.org/wiki/alcohol" class="extiw" title="wikt:alcohol">Definitions</a></b> from Wiktionary</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/14px-Commons-logo.svg.png" decoding="async" width="14" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/21px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/28px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></span><span class="sister-bar-link"><b><a href="https://commons.wikimedia.org/wiki/Category:Alcohols" class="extiw" title="c:Category:Alcohols">Media</a></b> from Commons</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/16px-Wikiquote-logo.svg.png" decoding="async" width="16" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/24px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/32px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wikiquote.org/wiki/Alcohol_(chemistry)" class="extiw" title="q:Alcohol (chemistry)">Quotations</a></b> from Wikiquote</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/18px-Wikisource-logo.svg.png" decoding="async" width="18" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/28px-Wikisource-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/36px-Wikisource-logo.svg.png 2x" data-file-width="410" data-file-height="430" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wikisource.org/wiki/Category:Alcohol" class="extiw" title="s:Category:Alcohol">Texts</a></b> from Wikisource</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/19px-Wikibooks-logo.svg.png" decoding="async" width="19" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/29px-Wikibooks-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/38px-Wikibooks-logo.svg.png 2x" data-file-width="300" data-file-height="300" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wikibooks.org/wiki/Organic_Chemistry/Alcohols" class="extiw" title="b:Organic Chemistry/Alcohols">Textbooks</a></b> from Wikibooks</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Wikiversity_logo_2017.svg/21px-Wikiversity_logo_2017.svg.png" decoding="async" width="21" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Wikiversity_logo_2017.svg/32px-Wikiversity_logo_2017.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Wikiversity_logo_2017.svg/42px-Wikiversity_logo_2017.svg.png 2x" data-file-width="626" data-file-height="512" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wikiversity.org/wiki/Category:Alcohol" class="extiw" title="v:Category:Alcohol">Resources</a></b> from Wikiversity</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Wikivoyage-Logo-v3-icon.svg/19px-Wikivoyage-Logo-v3-icon.svg.png" decoding="async" width="19" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Wikivoyage-Logo-v3-icon.svg/29px-Wikivoyage-Logo-v3-icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Wikivoyage-Logo-v3-icon.svg/38px-Wikivoyage-Logo-v3-icon.svg.png 2x" data-file-width="193" data-file-height="193" /></span></span></span><span class="sister-bar-link"><b><a href="https://en.wikivoyage.org/wiki/alcohol" class="extiw" title="voy:alcohol">Travel guides</a></b> from Wikivoyage</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/21px-Wikidata-logo.svg.png" decoding="async" width="21" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/32px-Wikidata-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/42px-Wikidata-logo.svg.png 2x" data-file-width="1050" data-file-height="590" /></span></span></span><span class="sister-bar-link"><b><a href="https://www.wikidata.org/wiki/Q156" class="extiw" title="d:Q156">Data</a></b> from Wikidata</span></li></ul></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 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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:Alcohols" title="Template:Alcohols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alcohols" title="Template talk:Alcohols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alcohols" title="Special:EditPage/Template:Alcohols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alcohols" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Alcohols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">By consumption</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/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Alcohols found in<br />alcoholic drinks</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/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohols_(medicine)" title="Alcohols (medicine)">Medical alcohol</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/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li>Methanol poisoning <ul><li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxic_alcohol" class="mw-redirect" title="Toxic alcohol">Toxic alcohols</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/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Primary_alcohol" title="Primary alcohol">Primary<br />alcohols</a> (1°)</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/Methanol" title="Methanol">Methanol</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/4-Methylcyclohexanemethanol" title="4-Methylcyclohexanemethanol">4-Methylcyclohexanemethanol</a></li> <li><a href="/wiki/Aminomethanol" title="Aminomethanol">Aminomethanol</a></li> <li><a href="/wiki/Cyclohexylmethanol" title="Cyclohexylmethanol">Cyclohexylmethanol</a></li> <li><a href="/wiki/Methoxymethanol" title="Methoxymethanol">Methoxymethanol</a></li> <li><a href="/wiki/Methylazoxymethanol" title="Methylazoxymethanol">Methylazoxymethanol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ethanol" title="Ethanol">Ethanol</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/1-Aminoethanol" title="1-Aminoethanol">1-Aminoethanol</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">2,2,2-Trichloroethanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-(2-Ethoxyethoxy)ethanol" title="2-(2-Ethoxyethoxy)ethanol">2-(2-Ethoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-Butoxyethanol" title="2-Butoxyethanol">2-Butoxyethanol</a></li> <li><a href="/wiki/2-Chloroethanol" title="2-Chloroethanol">2-Chloroethanol</a></li> <li><a href="/wiki/2-Ethoxyethanol" title="2-Ethoxyethanol">2-Ethoxyethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/2-Mercaptoethanol" title="2-Mercaptoethanol">2-Mercaptoethanol</a></li> <li><a href="/wiki/2-Methoxyethanol" title="2-Methoxyethanol">2-Methoxyethanol</a></li> <li><a href="/wiki/Aminoethylethanolamine" title="Aminoethylethanolamine">Aminoethylethanolamine</a></li> <li><a href="/wiki/Diethylethanolamine" title="Diethylethanolamine">Diethylethanolamine</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ethanolamine" title="Ethanolamine">Ethanolamine</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol"><i>N</i>,<i>N</i>-Diisopropylaminoethanol</a></li> <li><a href="/wiki/N-Methylethanolamine" title="N-Methylethanolamine"><i>N</i>-Methylethanolamine</a></li> <li><a href="/wiki/Phenoxyethanol" title="Phenoxyethanol">Phenoxyethanol</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Butanol" title="Butanol">Butanol</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/2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol"><i>n</i>-Butanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>1</sub> — C<sub>9</sub></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/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a></li> <li><a href="/wiki/1-Hexanol" title="1-Hexanol">1-Hexanol</a></li> <li><a href="/wiki/1-Heptanol" title="1-Heptanol">1-Heptanol</a></li> <li><a href="/wiki/1-Octanol" title="1-Octanol">1-Octanol</a> (capryl)</li> <li><a href="/wiki/1-Nonanol" title="1-Nonanol">1-Nonanol</a> (pelargonic)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>10</sub> — C<sub>19</sub></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/1-Decanol" title="1-Decanol">1-Decanol</a> (capric)</li> <li><a href="/wiki/1-Undecanol" class="mw-redirect" title="1-Undecanol">1-Undecanol</a> (hendecyl)</li> <li><a href="/wiki/1-Dodecanol" class="mw-redirect" title="1-Dodecanol">1-Dodecanol</a> (lauryl)</li> <li><a href="/wiki/1-Tridecanol" title="1-Tridecanol">1-Tridecanol</a></li> <li><a href="/wiki/1-Tetradecanol" title="1-Tetradecanol">1-Tetradecanol</a> (myristyl)</li> <li><a href="/wiki/1-Pentadecanol" title="1-Pentadecanol">1-Pentadecanol</a></li> <li><a href="/wiki/1-Hexadecanol" class="mw-redirect" title="1-Hexadecanol">1-Hexadecanol</a> (cetyl / palmityl)</li> <li><a href="/wiki/1-Heptadecanol" class="mw-redirect" title="1-Heptadecanol">1-Heptadecanol</a></li> <li><a href="/wiki/1-Octadecanol" class="mw-redirect" title="1-Octadecanol">1-Octadecanol</a> (stearyl)</li> <li><a href="/wiki/1-Nonadecanol" class="mw-redirect" title="1-Nonadecanol">1-Nonadecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>20</sub> — C<sub>29</sub></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/1-Icosanol" class="mw-redirect" title="1-Icosanol">1-Icosanol</a> (arachidyl)</li> <li><a href="/wiki/1-Heneicosanol" title="1-Heneicosanol">1-Heneicosanol</a></li> <li><a href="/wiki/1-Docosanol" title="1-Docosanol">1-Docosanol</a> (behenyl)</li> <li><a href="/w/index.php?title=1-Tricosanol&action=edit&redlink=1" class="new" title="1-Tricosanol (page does not exist)">1-Tricosanol</a></li> <li><a href="/wiki/1-Tetracosanol" title="1-Tetracosanol">1-Tetracosanol</a> (lignoceryl)</li> <li><a href="/w/index.php?title=1-Pentacosanol&action=edit&redlink=1" class="new" title="1-Pentacosanol (page does not exist)">1-Pentacosanol</a></li> <li><a href="/wiki/1-Hexacosanol" title="1-Hexacosanol">1-Hexacosanol</a> (ceryl)</li> <li><a href="/wiki/1-Heptacosanol" title="1-Heptacosanol">1-Heptacosanol</a></li> <li><a href="/wiki/1-Octacosanol" title="1-Octacosanol">1-Octacosanol</a> (cluytyl / montanyl)</li> <li><a href="/wiki/1-Nonacosanol" title="1-Nonacosanol">1-Nonacosanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>30</sub> — C<sub>39</sub></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/1-Triacontanol" title="1-Triacontanol">1-Triacontanol</a> (melissyl / myricyl)</li> <li><a href="/w/index.php?title=1-Hentriacontanol&action=edit&redlink=1" class="new" title="1-Hentriacontanol (page does not exist)">1-Hentriacontanol</a></li> <li><a href="/wiki/1-Dotriacontanol" title="1-Dotriacontanol">1-Dotriacontanol</a> (lacceryl)</li> <li><a href="/w/index.php?title=1-Tritriacontanol&action=edit&redlink=1" class="new" title="1-Tritriacontanol (page does not exist)">1-Tritriacontanol</a></li> <li><a href="/w/index.php?title=1-Tetratriacontanol&action=edit&redlink=1" class="new" title="1-Tetratriacontanol (page does not exist)">1-Tetratriacontanol</a> (geddyl)</li> <li><a href="/w/index.php?title=1-Pentatriacontanol&action=edit&redlink=1" class="new" title="1-Pentatriacontanol (page does not exist)">1-Pentatriacontanol</a></li> <li><a href="/w/index.php?title=1-Hexatriacontanol&action=edit&redlink=1" class="new" title="1-Hexatriacontanol (page does not exist)">1-Hexatriacontanol</a></li> <li><a href="/w/index.php?title=1-Heptatriacontanol&action=edit&redlink=1" class="new" title="1-Heptatriacontanol (page does not exist)">1-Heptatriacontanol</a></li> <li><a href="/w/index.php?title=1-Octatriacontanol&action=edit&redlink=1" class="new" title="1-Octatriacontanol (page does not exist)">1-Octatriacontanol</a></li> <li><a href="/w/index.php?title=1-Nonatriacontanol&action=edit&redlink=1" class="new" title="1-Nonatriacontanol (page does not exist)">1-Nonatriacontanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>40</sub> — C<sub>49</sub></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="/w/index.php?title=1-Tetracontanol&action=edit&redlink=1" class="new" title="1-Tetracontanol (page does not exist)">1-Tetracontanol</a></li> <li><a href="/w/index.php?title=1-Hentetracontanol&action=edit&redlink=1" class="new" title="1-Hentetracontanol (page does not exist)">1-Hentetracontanol</a></li> <li><a href="/w/index.php?title=1-Dotetracontanol&action=edit&redlink=1" class="new" title="1-Dotetracontanol (page does not exist)">1-Dotetracontanol</a></li> <li><a href="/w/index.php?title=1-Tritetracontanol&action=edit&redlink=1" class="new" title="1-Tritetracontanol (page does not exist)">1-Tritetracontanol</a></li> <li><a href="/w/index.php?title=1-Tetratetracontanol&action=edit&redlink=1" class="new" title="1-Tetratetracontanol (page does not exist)">1-Tetratetracontanol</a></li> <li><a href="/w/index.php?title=1-Pentatetracontanol&action=edit&redlink=1" class="new" title="1-Pentatetracontanol (page does not exist)">1-Pentatetracontanol</a></li> <li><a href="/w/index.php?title=1-Hexatetracontanol&action=edit&redlink=1" class="new" title="1-Hexatetracontanol (page does not exist)">1-Hexatetracontanol</a></li> <li><a href="/w/index.php?title=1-Heptatetracontanol&action=edit&redlink=1" class="new" title="1-Heptatetracontanol (page does not exist)">1-Heptatetracontanol</a></li> <li><a href="/w/index.php?title=1-Octatetracontanol&action=edit&redlink=1" class="new" title="1-Octatetracontanol (page does not exist)">1-Octatetracontanol</a></li> <li><a href="/w/index.php?title=1-Nonatetracontanol&action=edit&redlink=1" class="new" title="1-Nonatetracontanol (page does not exist)">1-Nonatetracontanol</a></li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/2-Ethylhexanol" title="2-Ethylhexanol">2-Ethylhexanol</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Anisyl_alcohol" title="Anisyl alcohol">Anisyl alcohol</a></li> <li><a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/Cinnamyl_alcohol" title="Cinnamyl alcohol">Cinnamyl alcohol</a></li> <li><a href="/wiki/Crotyl_alcohol" title="Crotyl alcohol">Crotyl alcohol</a></li> <li><a href="/wiki/Furfuryl_alcohol" title="Furfuryl alcohol">Furfuryl alcohol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Neopentyl_alcohol" title="Neopentyl alcohol">Neopentyl alcohol</a></li> <li><a href="/wiki/Nicotinyl_alcohol" title="Nicotinyl alcohol">Nicotinyl alcohol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">Propargyl alcohol</a></li> <li><a href="/wiki/Salicyl_alcohol" title="Salicyl alcohol">Salicyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li> <li><a href="/wiki/Vanillyl_alcohol" title="Vanillyl alcohol">Vanillyl alcohol</a></li> <li><a href="/wiki/Veratrole_alcohol" title="Veratrole alcohol">Veratrole alcohol</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Secondary<br /> alcohols (2°)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/1-Phenylethanol" title="1-Phenylethanol">1-Phenylethanol</a></li> <li><a href="/wiki/2-Butanol" title="2-Butanol">2-Butanol</a></li> <li><a href="/w/index.php?title=2-Deoxyerythritol&action=edit&redlink=1" class="new" title="2-Deoxyerythritol (page does not exist)">2-Deoxyerythritol</a></li> <li><a href="/wiki/2-Heptanol" title="2-Heptanol">2-Heptanol</a></li> <li><a href="/wiki/3-Heptanol" title="3-Heptanol">3-Heptanol</a></li> <li><a href="/wiki/2-Hexanol" title="2-Hexanol">2-Hexanol</a></li> <li><a href="/wiki/3-Hexanol" title="3-Hexanol">3-Hexanol</a></li> <li><a href="/wiki/3-Methyl-2-butanol" title="3-Methyl-2-butanol">3-Methyl-2-butanol</a></li> <li><a href="/wiki/2-Nonanol" title="2-Nonanol">2-Nonanol</a></li> <li><a href="/wiki/2-Octanol" title="2-Octanol">2-Octanol</a></li> <li><a href="/wiki/2-Pentanol" title="2-Pentanol">2-Pentanol</a></li> <li><a href="/wiki/3-Pentanol" title="3-Pentanol">3-Pentanol</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/Cyclopentanol" title="Cyclopentanol">Cyclopentanol</a></li> <li><a href="/wiki/Cyclopropanol" title="Cyclopropanol">Cyclopropanol</a></li> <li><a href="/wiki/Diphenylmethanol" title="Diphenylmethanol">Diphenylmethanol</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Pirkle%27s_alcohol" title="Pirkle's alcohol">Pirkle's alcohol</a></li> <li><a href="/wiki/Propylene_glycol_methyl_ether" title="Propylene glycol methyl ether">Propylene glycol methyl ether</a></li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tertiary<br /> alcohols (3°)</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/2-Methyl-2-pentanol" title="2-Methyl-2-pentanol">2-Methyl-2-pentanol</a></li> <li><a href="/w/index.php?title=2-Methylheptan-2-ol&action=edit&redlink=1" class="new" title="2-Methylheptan-2-ol (page does not exist)">2-Methylheptan-2-ol</a></li> <li><a href="/w/index.php?title=2-Methylhexan-2-ol&action=edit&redlink=1" class="new" title="2-Methylhexan-2-ol (page does not exist)">2-Methylhexan-2-ol</a></li> <li><a href="/wiki/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=3-Methyloctan-3-ol&action=edit&redlink=1" class="new" title="3-Methyloctan-3-ol (page does not exist)">3-Methyloctan-3-ol</a></li> <li><a href="/wiki/Diacetone_alcohol" title="Diacetone alcohol">Diacetone alcohol</a></li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li> <li><a href="/wiki/Triphenylethanol" title="Triphenylethanol">Triphenylethanol</a></li> <li><a href="/wiki/Triphenylmethanol" title="Triphenylmethanol">Triphenylmethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydric alcohols</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%">Monohydric alcohols</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/Methanol" title="Methanol">Methanol</a> (C<sub>1</sub>)</li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> (C<sub>16</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dihydric alcohols</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/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trihydric alcohols</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/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Polyhydric alcohols (sugar alcohols)</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/Pentaerythritol" title="Pentaerythritol">Pentaerythritol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a>, <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a>, <a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>, <a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amyl_alcohol" title="Amyl alcohol">Amyl alcohols</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/2,2-Dimethylpropan-1-ol" class="mw-redirect" title="2,2-Dimethylpropan-1-ol">2,2-Dimethylpropan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-1-ol" class="mw-redirect" title="2-Methylbutan-1-ol">2-Methylbutan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-2-ol" class="mw-redirect" title="2-Methylbutan-2-ol">2-Methylbutan-2-ol </a></li> <li><a href="/wiki/3-Methylbutan-1-ol" class="mw-redirect" title="3-Methylbutan-1-ol">3-Methylbutan-1-ol </a></li> <li><a href="/wiki/3-Methylbutan-2-ol" class="mw-redirect" title="3-Methylbutan-2-ol">3-Methylbutan-2-ol </a></li> <li><a href="/wiki/Pentan-1-ol" class="mw-redirect" title="Pentan-1-ol">Pentan-1-ol </a></li> <li><a href="/wiki/Pentan-2-ol" class="mw-redirect" title="Pentan-2-ol">Pentan-2-ol </a></li> <li><a href="/wiki/Pentan-3-ol" class="mw-redirect" title="Pentan-3-ol">Pentan-3-ol </a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Aromatic alcohols</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/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/2,4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">2,4-Dichlorobenzyl alcohol</a></li> <li><a href="/wiki/3-Nitrobenzyl_alcohol" title="3-Nitrobenzyl alcohol">3-Nitrobenzyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Saturated<br /><a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</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/Cetostearyl_alcohol" title="Cetostearyl alcohol">Cetostearyl alcohol</a></li> <li><a href="/wiki/Decanol" class="mw-redirect" title="Decanol">Decanol</a></li> <li><a href="/wiki/Lauryl_alcohol" class="mw-redirect" title="Lauryl alcohol">Lauryl alcohol</a></li> <li><a href="/wiki/Myristyl_alcohol" class="mw-redirect" title="Myristyl alcohol">Myristyl alcohol</a></li> <li><a href="/wiki/Nonanol_(disambiguation)" class="mw-redirect mw-disambig" title="Nonanol (disambiguation)">Nonanol</a></li> <li><a href="/wiki/Octanol" title="Octanol">Octanol</a></li> <li><a href="/wiki/Tridecanol" class="mw-redirect" title="Tridecanol">Tridecanol</a></li> <li><a href="/wiki/Undecanol" title="Undecanol">Undecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Branched and<br />unsaturated<br /><a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</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/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=Erucyl_alcohol&action=edit&redlink=1" class="new" title="Erucyl alcohol (page does not exist)">Erucyl alcohol</a></li> <li><a href="/w/index.php?title=Linolenyl_alcohol&action=edit&redlink=1" class="new" title="Linolenyl alcohol (page does not exist)">Linolenyl alcohol</a></li> <li><a href="/wiki/Linoleyl_alcohol" title="Linoleyl alcohol">Linoleyl alcohol</a></li> <li><a href="/wiki/Oleyl_alcohol" title="Oleyl alcohol">Oleyl alcohol</a></li> <li><a href="/w/index.php?title=Palmitoleyl_alcohol&action=edit&redlink=1" class="new" title="Palmitoleyl alcohol (page does not exist)">Palmitoleyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohols</a></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%">C<sub>1</sub> — C<sub>7</sub></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/Methylene_glycol" class="mw-redirect" title="Methylene glycol">Methylene glycol</a> (C<sub>1</sub>)</li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Arabitol" title="Arabitol">Arabitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Ribitol" title="Ribitol">Ribitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Galactitol" title="Galactitol">Galactitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Iditol" title="Iditol">Iditol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Deoxy sugar<br /> alcohols</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/Fucitol" title="Fucitol">Fucitol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cyclic sugar<br /> alcohols</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/Inositol" title="Inositol">Inositol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycylglycitols</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/Maltitol" title="Maltitol">Maltitol</a></li> <li><a href="/wiki/Lactitol" title="Lactitol">Lactitol</a></li> <li><a href="/wiki/Isomalt" title="Isomalt">Isomalt</a></li> <li><a href="/w/index.php?title=Maltotriitol&action=edit&redlink=1" class="new" title="Maltotriitol (page does not exist)">Maltotriitol</a></li> <li><a href="/w/index.php?title=Maltotetraitol&action=edit&redlink=1" class="new" title="Maltotetraitol (page does not exist)">Maltotetraitol</a></li> <li><a href="/w/index.php?title=Polyglycitol&action=edit&redlink=1" class="new" title="Polyglycitol (page does not exist)">Polyglycitol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Terpene alcohols</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%">Monoterpene<br /> alcohols</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/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Nerol" title="Nerol">Nerol</a></li> <li><a href="/wiki/Rhodinol" title="Rhodinol">Rhodinol</a></li> <li><a href="/wiki/Terpineol" title="Terpineol">Terpineol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquiterpene<br /> alcohols</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/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Farnesol" title="Farnesol">Farnesol</a></li> <li><a href="/wiki/Nerolidol" title="Nerolidol">Nerolidol</a></li> <li><a href="/wiki/Patchoulol" title="Patchoulol">Patchoulol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diterpene<br /> alcohols</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/Phytol" title="Phytol">Phytol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dialcohols</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/1,4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li> <li><a href="/wiki/1,5-Pentanediol" title="1,5-Pentanediol">1,5-Pentanediol</a></li> <li><a href="/wiki/2-Methyl-2-propyl-1,3-propanediol" title="2-Methyl-2-propyl-1,3-propanediol">2-Methyl-2-propyl-1,3-propanediol</a></li> <li><a href="/wiki/Diethylpropanediol" class="mw-redirect" title="Diethylpropanediol">Diethylpropanediol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trialcohols</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/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sterols</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/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fluoroalcohol" title="Fluoroalcohol">Fluoroalcohols</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/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</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/Substitution_reaction" title="Substitution reaction">Substitution</a> of <a href="/wiki/Haloalkane#Substitution" title="Haloalkane">haloalkane</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Ether_cleavage" title="Ether cleavage">Ether cleavage</a></li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of <a href="/wiki/Epoxide#Hydrolysis_and_addition_of_nucleophiles" title="Epoxide">epoxide</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a> of <a href="/wiki/Alkene#Hydration" title="Alkene">alkene</a></li> <li><a href="/wiki/Ziegler_process" title="Ziegler process">Ziegler process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</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/Deprotonation" title="Deprotonation">Deprotonation</a></li> <li><a href="/wiki/Protonation" title="Protonation">Protonation</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a> <ul><li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li></ul></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a></li> <li><a href="/wiki/Fischer%E2%80%93Speier_esterification" title="Fischer–Speier esterification">Fischer–Speier esterification</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a> of <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a></li> <li><a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a></li> <li><a href="/wiki/Nucleophilic_conjugate_addition" title="Nucleophilic conjugate addition">Nucleophilic conjugate addition</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Alcohols" title="Category:Alcohols">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Alcohol" style="padding:3px"><table class="nowraplinks 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alcohol_and_health" title="Template:Alcohol and health"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alcohol_and_health" title="Template talk:Alcohol and health"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alcohol_and_health" title="Special:EditPage/Template:Alcohol and health"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alcohol" style="font-size:114%;margin:0 4em"><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol</a><br /> use</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol-related_crime" title="Alcohol-related crime">Alcohol-related<br /> crimes</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/Drunk_driving" title="Drunk driving">Drunk driving</a> <ul><li><a href="/wiki/Alcohol-related_traffic_crashes_in_the_United_States" title="Alcohol-related traffic crashes in the United States">Alcohol-related traffic crashes in the United States</a></li> <li><a href="/wiki/Drunk_driving_in_the_United_States" title="Drunk driving in the United States">Drunk driving in the United States</a></li></ul></li> <li><a href="/wiki/Moonshine" title="Moonshine">Moonshine</a> <ul><li><a href="/wiki/Bathtub_gin" title="Bathtub gin">Bathtub gin</a></li></ul></li> <li>Prison alcohol <ul><li><a href="/wiki/P%C3%A1jaro_verde" title="Pájaro verde">Pájaro verde</a></li> <li><a href="/wiki/Pruno" title="Pruno">Pruno</a></li></ul></li> <li><a href="/wiki/Public_intoxication" title="Public intoxication">Public intoxication</a></li> <li><a href="/wiki/Rum-running" title="Rum-running">Rum-running</a></li> <li><a href="/wiki/Sly-grog_shop" title="Sly-grog shop">Sly-grog shop</a></li> <li><a href="/wiki/Wine_fraud" title="Wine fraud">Wine fraud</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcoholism" title="Alcoholism">Alcoholism</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/Alcohol_and_Native_Americans" title="Alcohol and Native Americans">Alcohol and Native Americans</a></li> <li><a href="/wiki/Alcoholism_in_adolescence" title="Alcoholism in adolescence">Alcoholism in adolescence</a></li> <li><a href="/wiki/Alcoholism_in_family_systems" title="Alcoholism in family systems">Alcoholism in family systems</a></li> <li><a href="/wiki/Alcoholism_in_rural_Australia" title="Alcoholism in rural Australia">Alcoholism in rural Australia</a></li> <li><a href="/wiki/Collaborative_Study_on_the_Genetics_of_Alcoholism" title="Collaborative Study on the Genetics of Alcoholism">Collaborative Study on the Genetics of Alcoholism</a></li> <li><a href="/wiki/Disease_theory_of_alcoholism" title="Disease theory of alcoholism">Disease theory of alcoholism</a></li> <li><a href="/wiki/High-functioning_alcoholic" title="High-functioning alcoholic">High-functioning alcoholic</a> (HFA)</li> <li><a href="/wiki/Seeing_pink_elephants" title="Seeing pink elephants">Seeing pink elephants</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chemistry</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Beverage-specific <ul><li><a href="/wiki/Beer_chemistry" title="Beer chemistry">Beer chemistry</a></li> <li><a href="/wiki/Wine_chemistry" title="Wine chemistry">Wine chemistry</a></li></ul></li> <li><a href="/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Comparison of psychoactive alcohols in alcoholic drinks</a></li> <li><a href="/wiki/Congener_(beverages)" title="Congener (beverages)">Congener</a> <ul><li><a href="/wiki/Alcohol_congener_analysis" title="Alcohol congener analysis">Alcohol congener analysis</a></li></ul></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> <ul><li><a href="/wiki/Blood_alcohol_content" title="Blood alcohol content">Blood alcohol content</a></li></ul></li> <li><a href="/wiki/Fusel_alcohol" title="Fusel alcohol">Fusel alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Effects</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/Short-term_effects_of_alcohol_consumption" title="Short-term effects of alcohol consumption">Short-term effects of alcohol consumption</a></li> <li><a href="/wiki/Long-term_effects_of_alcohol" title="Long-term effects of alcohol">Long-term effects of alcohol</a></li> <li><a href="/wiki/Pharmacology_of_ethanol" title="Pharmacology of ethanol">Pharmacology of ethanol</a></li> <li><a href="/wiki/Subjective_response_to_alcohol" title="Subjective response to alcohol">Subjective response to alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Adverse effects</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/Hangxiety" title="Hangxiety">Anxiety</a></li> <li><a href="/wiki/Impact_of_alcohol_on_aging" title="Impact of alcohol on aging">Aging</a></li> <li><a href="/wiki/Long-term_impact_of_alcohol_on_the_brain" title="Long-term impact of alcohol on the brain">Brain</a></li> <li><a href="/wiki/Alcohol_and_cancer" title="Alcohol and cancer">Cancer</a> <ul><li><a href="/wiki/Alcohol_and_breast_cancer" title="Alcohol and breast cancer">breast cancer</a></li></ul></li> <li><a href="/wiki/Alcohol_and_cortisol" title="Alcohol and cortisol">Cortisol</a></li> <li><a href="/wiki/Effects_of_alcohol_on_memory" title="Effects of alcohol on memory">Memory</a></li> <li><a href="/wiki/Alcohol_and_pregnancy" class="mw-redirect" title="Alcohol and pregnancy">Pregnancy</a></li> <li><a href="/wiki/Alcohol_use_and_sleep" title="Alcohol use and sleep">Sleep</a></li> <li><a href="/wiki/Alcohol_tolerance" title="Alcohol tolerance">Tolerance</a>/<a href="/wiki/Alcohol_intolerance" title="Alcohol intolerance">intolerance</a></li> <li><a href="/wiki/Alcohol_and_weight" title="Alcohol and weight">Weight</a></li> <li>Beverage-specific <ul><li>Beer: <a href="/wiki/Potomania" title="Potomania">Potomania</a></li> <li>Wine: <a href="/wiki/Red_wine_headache" title="Red wine headache">Red wine headache</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Social_issues" class="mw-redirect" title="Social issues">Social issues</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>Adulterated alcohol <ul><li><a href="/wiki/Moonshine#Adulterated_moonshine" title="Moonshine">Adulterated moonshine</a></li> <li><a href="/wiki/Denatured_alcohol" title="Denatured alcohol">Denatured alcohol</a> (<a href="/wiki/List_of_methanol_poisoning_incidents" title="List of methanol poisoning incidents">List of methanol poisoning incidents</a>)</li> <li><a href="/wiki/Surrogate_alcohol" title="Surrogate alcohol">Surrogate alcohol</a></li></ul></li> <li><a href="/wiki/Alcohol_abuse" title="Alcohol abuse">Alcohol abuse</a></li> <li><a href="/wiki/Alcohol_advertising" title="Alcohol advertising">Alcohol advertising</a> <ul><li><a href="/wiki/Alcohol_advertising_on_college_campuses" title="Alcohol advertising on college campuses">on college campuses</a></li></ul></li> <li><a href="/wiki/Alcohol_and_sex" title="Alcohol and sex">Sex</a> <ul><li><a href="/wiki/Beer_goggles" title="Beer goggles">Beer goggles</a></li></ul></li> <li><a href="/wiki/Alcohol_myopia" title="Alcohol myopia">Alcohol myopia</a></li> <li><a href="/wiki/Alcohol_in_association_football" title="Alcohol in association football">Alcohol in association football</a></li> <li><a href="/wiki/Alcohol_use_among_college_students" title="Alcohol use among college students">Alcohol use among college students</a></li> <li><a href="/wiki/Binge_drinking" title="Binge drinking">Binge drinking</a> <ul><li><a href="/wiki/Austrian_syndrome" title="Austrian syndrome">Austrian syndrome</a></li> <li><a href="/wiki/Alcohol_intoxication" title="Alcohol intoxication">Alcohol intoxication</a></li> <li><a href="/wiki/Epidemiology_of_binge_drinking" title="Epidemiology of binge drinking">Epidemiology of binge drinking</a></li> <li><a href="/wiki/Holiday_heart_syndrome" title="Holiday heart syndrome">Holiday heart syndrome</a></li> <li>Problematic alcoholic products <ul><li><a href="/wiki/Alcohol_powder" title="Alcohol powder">Alcohol powder</a></li> <li><a href="/wiki/Alcopop" title="Alcopop">Alcopop</a></li> <li><a href="/wiki/Borg_(drink)" title="Borg (drink)">Borg</a></li> <li>Low-cost alcohol <ul><li><a href="/wiki/Flavored_fortified_wine" title="Flavored fortified wine">Flavored fortified wine</a></li></ul></li> <li><a href="/wiki/Alcohol_(drug)#Stimulants" title="Alcohol (drug)">Polysubstance alcoholic drinks</a> <ul><li><a href="/wiki/Caffeinated_alcoholic_drink" title="Caffeinated alcoholic drink">Caffeinated alcoholic drink</a></li> <li><a href="/wiki/Coca_wine" title="Coca wine">Coca wine</a></li> <li><a href="/wiki/Nicotini" title="Nicotini">Nicotini</a></li></ul></li></ul></li> <li><a href="/wiki/Zapoy" title="Zapoy">Zapoy</a></li></ul></li> <li><a href="/wiki/Blackout_(drug-related_amnesia)" title="Blackout (drug-related amnesia)">Blackout</a></li> <li><a href="/wiki/Blackout_Wednesday" title="Blackout Wednesday">Blackout Wednesday</a></li> <li><a href="/wiki/Drinking_game" title="Drinking game">Drinking game</a> <ul><li><a href="/wiki/List_of_drinking_games" title="List of drinking games">list</a></li> <li><a href="/wiki/Pregaming" title="Pregaming">Pregaming</a></li></ul></li> <li><a href="/wiki/Drinking_in_public" title="Drinking in public">Drinking in public</a></li> <li><a href="/wiki/Drunk_walking" title="Drunk walking">Drunk walking</a></li> <li><a href="/wiki/Drunkorexia" title="Drunkorexia">Drunkorexia</a></li> <li><a href="/wiki/Dry_drunk" title="Dry drunk">Dry drunk</a></li> <li><a href="/wiki/Dutch_courage" title="Dutch courage">Dutch courage</a></li> <li><a href="/wiki/Flaming_drink" title="Flaming drink">Flaming drink</a></li> <li><a href="/wiki/Hair_of_the_dog" title="Hair of the dog">Hair of the dog</a></li> <li><a href="/wiki/Hurtful_communication#Alcohol" title="Hurtful communication">Hurtful communication</a> <ul><li><a href="/wiki/Drunk_dialing" title="Drunk dialing">Drunk dialing</a></li> <li><a href="/wiki/In_vino_veritas" title="In vino veritas"><i>In vino veritas</i></a></li></ul></li> <li><a href="/wiki/Nightcap_(drink)" title="Nightcap (drink)">Nightcap</a></li> <li><a href="/wiki/Pantsdrunk" title="Pantsdrunk">Pantsdrunk</a></li> <li><a href="/wiki/Passive_drinking" title="Passive drinking">Passive drinking</a></li> <li>Binge drinking devices <ul><li><a href="/wiki/Beer_bong" title="Beer bong">Beer bong</a></li> <li><a href="/wiki/Yard_of_ale" title="Yard of ale">Yard of ale</a></li></ul></li> <li>Routes of administration <ul><li><a href="/wiki/Alcohol_enema" title="Alcohol enema">Alcohol enema</a></li> <li><a href="/wiki/Alcohol_inhalation" title="Alcohol inhalation">Alcohol inhalation</a></li> <li><a href="/wiki/Vodka_eyeballing" title="Vodka eyeballing">Vodka eyeballing</a></li></ul></li> <li><a href="/wiki/Sconcing" title="Sconcing">Sconcing</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</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/Andrew_Johnson_alcoholism_debate" title="Andrew Johnson alcoholism debate">Andrew Johnson alcoholism debate</a></li> <li><a href="/wiki/Dionysian_Mysteries" title="Dionysian Mysteries">Dionysian Mysteries</a></li> <li><a href="/wiki/Dipsomania" title="Dipsomania">Dipsomania</a></li> <li><a href="/wiki/Gilbert_Paul_Jordan" title="Gilbert Paul Jordan">Gilbert Paul Jordan</a></li> <li><a href="/wiki/Gin_Craze" title="Gin Craze">Gin Craze</a></li> <li><a href="/wiki/List_of_deaths_through_alcohol" title="List of deaths through alcohol">List of deaths through alcohol</a></li> <li><a href="/wiki/Rum_ration" title="Rum ration">Rum ration</a></li> <li><a href="/wiki/Rum_Rebellion" title="Rum Rebellion">Rum Rebellion</a></li> <li><a href="/wiki/Shebeen" title="Shebeen">Shebeen</a></li> <li><a href="/wiki/Six_o%27clock_swill" title="Six o'clock swill">Six o'clock swill</a></li> <li>Illegal drinking establishments <ul><li><a href="/wiki/Nip_joint" title="Nip joint">Nip joint</a></li> <li><a href="/wiki/Speakeasy" title="Speakeasy">Speakeasy</a></li></ul></li> <li><a href="/wiki/Whiskey_Rebellion" title="Whiskey Rebellion">Whiskey Rebellion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Alcoholic_beverage" title="Alcoholic beverage">Alcoholic beverage</a></li> <li>Beer <ul><li><a href="/wiki/Beer_mile" title="Beer mile">Beer mile</a></li> <li><a href="/wiki/International_Beer_Day" title="International Beer Day">International Beer Day</a></li> <li><a href="/wiki/International_Women%27s_Collaboration_Brew_Day" title="International Women's Collaboration Brew Day">International Women's Collaboration Brew Day</a></li> <li><a href="/wiki/Women_in_brewing" title="Women in brewing">Women in brewing</a></li></ul></li> <li><a href="/wiki/Drinking_culture" title="Drinking culture">Drinking culture</a> <ul><li><a href="/wiki/Ap%C3%A9ritif_and_digestif" title="Apéritif and digestif">Apéritif and digestif</a></li> <li><a href="/wiki/Hangover_remedies" title="Hangover remedies">Hangover remedies</a></li> <li><a href="/wiki/Health_effects_of_wine" title="Health effects of wine">Health effects of wine</a> <ul><li><a href="/wiki/Wine_and_food_pairing" title="Wine and food pairing">Wine and food pairing</a></li></ul></li></ul></li> <li><a href="/wiki/Drunken_monkey_hypothesis" title="Drunken monkey hypothesis">Drunken monkey hypothesis</a></li> <li><a href="/wiki/Ladies%27_night" title="Ladies' night">Ladies' night</a></li> <li><a href="/wiki/List_of_countries_by_alcohol_consumption_per_capita" title="List of countries by alcohol consumption per capita">List of countries by alcohol consumption per capita</a> <ul><li><a href="/wiki/Alcohol_consumption_by_youth_in_the_United_States" title="Alcohol consumption by youth in the United States">Alcohol consumption by youth in the United States</a></li></ul></li> <li><a href="/wiki/List_of_substances_used_in_rituals#Alcohol" title="List of substances used in rituals">Ritual use of alcohol</a></li> <li>Whiskey <ul><li><a href="/wiki/International_whisk(e)y_day" title="International whisk(e)y day">International whisk(e)y day</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol <br />control</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_law" title="Alcohol law">Alcohol law</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/Administrative_License_Suspension" title="Administrative License Suspension">Administrative License Suspension</a> (ALS)</li> <li><a href="/wiki/Alcohol_(Minimum_Pricing)_(Scotland)_Act_2012" title="Alcohol (Minimum Pricing) (Scotland) Act 2012">Alcohol (Minimum Pricing) (Scotland) Act 2012</a></li> <li><a href="/wiki/Alcohol_exclusion_laws" title="Alcohol exclusion laws">Alcohol exclusion laws</a></li> <li><a href="/wiki/Alcohol_monopoly" title="Alcohol monopoly">Alcohol monopoly</a> <ul><li><a href="/wiki/Alcoholic_beverage_control_state" title="Alcoholic beverage control state">Alcoholic beverage control state</a></li></ul></li> <li><a href="/wiki/Alcohol_packaging_warning_messages" title="Alcohol packaging warning messages">Alcohol packaging warning messages</a></li> <li><a href="/wiki/Ban_on_caffeinated_alcoholic_drinks_in_the_United_States" title="Ban on caffeinated alcoholic drinks in the United States">Ban on caffeinated alcoholic drinks in the United States</a></li> <li><a href="/wiki/Drunk_driving_law_by_country" title="Drunk driving law by country">Drunk driving law by country</a> <ul><li><a href="/wiki/DWI_court" title="DWI court">DWI court</a></li> <li><a href="/wiki/Field_sobriety_testing" title="Field sobriety testing">Field sobriety testing</a></li> <li><a href="/wiki/Hip_flask_defence" title="Hip flask defence">Hip flask defence</a></li> <li><a href="/wiki/Ignition_interlock_device" title="Ignition interlock device">Ignition interlock device</a></li></ul></li> <li><a href="/wiki/Dry_county" title="Dry county">Dry county</a> <ul><li><a href="/wiki/List_of_dry_communities_by_U.S._state" title="List of dry communities by U.S. state">List of dry communities by U.S. state</a></li></ul></li> <li><a href="/wiki/Last_call" title="Last call">Last call</a></li> <li><a href="/wiki/Legal_drinking_age" title="Legal drinking age">Legal drinking age</a> <ul><li><a href="/wiki/Legal_drinking_age_in_the_United_States" title="Legal drinking age in the United States">Legal drinking age in the United States</a></li> <li><a href="/wiki/Shoulder_tap_(alcohol)" title="Shoulder tap (alcohol)">Shoulder tap</a></li></ul></li> <li><a href="/wiki/List_of_alcohol_laws_of_the_United_States" title="List of alcohol laws of the United States">List of alcohol laws of US</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prohibition" title="Prohibition">Alcohol prohibition</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/List_of_countries_with_alcohol_prohibition" title="List of countries with alcohol prohibition">List of countries with alcohol prohibition</a></li> <li><a href="/wiki/Neo-prohibitionism" title="Neo-prohibitionism">Neo-prohibitionism</a></li> <li><a href="/wiki/Temperance_movement" title="Temperance movement">Temperance movement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sobriety" title="Sobriety">Sobriety</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/Alcohol_detoxification" title="Alcohol detoxification">Alcohol detoxification</a></li> <li><a href="/wiki/Alcohol-free_zone" title="Alcohol-free zone">Alcohol-free zone</a> <ul><li><a href="/wiki/Dry_campus" title="Dry campus">Dry campus</a></li> <li><a href="/wiki/Open-container_law" title="Open-container law">Open-container law</a></li></ul></li> <li><a href="/wiki/Brief_intervention" title="Brief intervention">Brief intervention</a></li> <li><a href="/wiki/Designated_driver" title="Designated driver">Designated driver</a></li> <li><a href="/wiki/Drug_rehabilitation" title="Drug rehabilitation">Alcohol rehabilitation</a></li> <li><a href="/wiki/Drunk_tank" title="Drunk tank">Drunk tank</a></li> <li><a href="/wiki/Managed_alcohol_program" title="Managed alcohol program">Managed alcohol program</a></li> <li><a href="/wiki/Non-alcoholic_drink" title="Non-alcoholic drink">Non-alcoholic drink</a> <ul><li><a href="/wiki/List_of_non-alcoholic_cocktails" class="mw-redirect" title="List of non-alcoholic cocktails">List of cocktails</a></li> <li><a href="/wiki/List_of_non-alcoholic_mixed_drinks" title="List of non-alcoholic mixed drinks">List of mixed drinks</a></li> <li><a href="/wiki/Spritzer#Non-alcoholic_spritzer" title="Spritzer">Spritzer</a></li> <li><a href="/wiki/Malt_drink#Non-alcoholic_malt_drinks" title="Malt drink">Malt drinks</a></li></ul></li> <li><a href="/wiki/Teetotalism" title="Teetotalism">Teetotalism</a></li> <li><a href="/wiki/Temperance_bar" title="Temperance bar">Temperance bar</a></li> <li><a href="/wiki/Temperance_and_Good_Citizenship_Day" title="Temperance and Good Citizenship Day">Temperance and Good Citizenship Day</a></li> <li><a href="/wiki/List_of_twelve-step_groups" title="List of twelve-step groups">Twelve-step groups</a> <ul><li><a href="/wiki/Al-Anon/Alateen" title="Al-Anon/Alateen">Al-Anon/Alateen</a></li> <li><a href="/wiki/Alcoholics_Anonymous" title="Alcoholics Anonymous">Alcoholics Anonymous</a> (AA):</li> <li><a href="/wiki/Adult_Children_of_Alcoholics" class="mw-redirect" title="Adult Children of Alcoholics">Adult Children of Alcoholics</a> (ACA)</li></ul></li> <li><a href="/wiki/Sober_companion" title="Sober companion">Sober companion</a></li> <li><a href="/wiki/Sober_curious" title="Sober curious">Sober curious</a></li> <li><a href="/wiki/Sober_living_house" title="Sober living house">Sober living house</a></li> <li><a href="/wiki/Sobering_center" title="Sobering center">Sobering center</a></li> <li><a href="/wiki/Sobrietol" title="Sobrietol">Sobrietol</a></li> <li><a href="/wiki/Quit_lit_(alcohol_cessation)" title="Quit lit (alcohol cessation)">Quit lit</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol limitation</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/0-0-1-3" title="0-0-1-3">0-0-1-3</a></li> <li><a href="/wiki/Alcohol_consumption_recommendations" title="Alcohol consumption recommendations">Alcohol consumption recommendations</a></li> <li><a href="/wiki/Alcohol_education" title="Alcohol education">Alcohol education</a></li> <li><a href="/wiki/Alcohol_server_training" title="Alcohol server training">Alcohol server training</a></li> <li>Monitoring <ul><li><a href="/wiki/Breathalyzer" title="Breathalyzer">Breathalyzer</a></li> <li><a href="/wiki/Electronic_tagging#Sweat_alcohol_content_monitor" title="Electronic tagging">Sweat alcohol content monitor</a></li></ul></li> <li><a href="/wiki/Brief_intervention#FRAMES" title="Brief intervention">FRAMES</a></li> <li><a href="/wiki/Foundation_for_Advancing_Alcohol_Responsibility" title="Foundation for Advancing Alcohol Responsibility">Foundation for Advancing Alcohol Responsibility</a></li> <li>Campaigns <ul><li><a href="/wiki/Dry_January" title="Dry January">Dry January</a></li> <li><a href="/wiki/Dry_July" title="Dry July">Dry July</a></li> <li><a href="/wiki/Get_Your_Sexy_Back" title="Get Your Sexy Back">Get Your Sexy Back</a></li> <li><a href="/wiki/Ocsober" title="Ocsober">Ocsober</a></li></ul></li> <li><a href="/wiki/Liquor_license" title="Liquor license">Liquor license</a></li> <li>Low-alcohol drinks <ul><li><a href="/wiki/Fermented_tea" title="Fermented tea">Fermented tea</a></li> <li><a href="/wiki/Low-alcohol_beer" title="Low-alcohol beer">Low-alcohol beer</a></li> <li><a href="/wiki/Malt_drink#Low-alcoholic_malt_drinks" title="Malt drink">Low-alcoholic malt drinks</a></li> <li><a href="/wiki/Small_beer" title="Small beer">Small beer</a></li></ul></li> <li>Measurement <ul><li><a href="/wiki/Alcoholic_spirits_measure" title="Alcoholic spirits measure">Alcoholic spirits measure</a></li> <li><a href="/wiki/Standard_drink" title="Standard drink">Standard drink</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addiction_medicine" title="Addiction medicine">Addiction medicine</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/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> <ul><li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li></ul></li> <li><a href="/wiki/Disulfiram-like_drug" title="Disulfiram-like drug">Disulfiram-like drugs</a> <ul><li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Calcium_carbimide" title="Calcium carbimide">Calcium carbimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li></ul></li> <li><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anaesthetics</a> <ul><li><a href="/wiki/Nitrous_oxide_(medication)" title="Nitrous oxide (medication)">Nitrous oxide</a></li></ul></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acids</a> <ul><li><a href="/wiki/Acamprosate" title="Acamprosate">Acamprosate</a></li> <li><a href="/wiki/Homotaurine" title="Homotaurine">Homotaurine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Religion_and_alcohol" title="Religion and alcohol">Religion and alcohol</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/Christian_views_on_alcohol" title="Christian views on alcohol">Christian views on alcohol</a> <ul><li><a href="/wiki/Alcohol_in_the_Bible" title="Alcohol in the Bible">Alcohol in the Bible</a></li></ul></li> <li><a href="/wiki/Khamr" title="Khamr">Islam and alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</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/Beer_Street_and_Gin_Lane" title="Beer Street and Gin Lane"><i>Beer Street</i> and <i>Gin Lane</i></a></li> <li><a href="/wiki/Bratt_System" title="Bratt System">Bratt System</a></li> <li><a href="/wiki/Dry_state" title="Dry state">Dry state</a></li> <li><a href="/wiki/Gin_Act_1751" title="Gin Act 1751">Gin Act 1751</a></li> <li><a href="/wiki/Medicinal_Liquor_Prescriptions_Act_of_1933" title="Medicinal Liquor Prescriptions Act of 1933">Medicinal Liquor Prescriptions Act of 1933</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Index_of_alcohol-related_articles" title="Index of alcohol-related articles">Index of alcohol-related articles</a></li> <li><a href="/wiki/Alcohol_and_spaceflight" title="Alcohol and spaceflight">Alcohol and spaceflight</a></li> <li><a href="/wiki/Gateway_drug_effect" title="Gateway drug effect">Gateway drug effect</a></li> <li><a href="/wiki/Mood_disorder" title="Mood disorder">Mood disorder</a></li> <li><a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">Non-alcoholic fatty liver disease</a></li> <li><a href="/wiki/Self-medication" title="Self-medication">Self-medication</a></li> <li><a href="/wiki/Spins" title="Spins">Spins</a></li> <li><a href="/wiki/Town_drunk" title="Town drunk">Town drunk</a></li> <li><a href="/wiki/French_paradox" title="French paradox">French paradox</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Alcohol_and_health" title="Category:Alcohol and health">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a class="mw-selflink selflink">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" aria-labelledby="*_Poisoning_*_Toxicity_*_Overdose" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Poisoning_and_toxicity" title="Template:Poisoning and toxicity"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Poisoning_and_toxicity" title="Template talk:Poisoning and toxicity"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Poisoning_and_toxicity" title="Special:EditPage/Template:Poisoning and toxicity"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="*_Poisoning_*_Toxicity_*_Overdose" class="hlist" style="font-size:114%;margin:0 4em"> <ul><li><a href="/wiki/Poisoning" title="Poisoning">Poisoning</a></li> <li><a href="/wiki/Toxicity" title="Toxicity">Toxicity</a></li> <li><a href="/wiki/Drug_overdose" title="Drug overdose">Overdose</a></li></ul> </div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Poison" title="Poison">Poison</a></li> <li><a href="/wiki/History_of_poison" title="History of poison">History</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></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/Metal" title="Metal">Metals</a></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/Toxic_metal" class="mw-redirect" title="Toxic metal">Toxic metals</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/Beryllium_poisoning" title="Beryllium poisoning">Beryllium</a></li> <li><a href="/wiki/Cadmium_poisoning" title="Cadmium poisoning">Cadmium</a></li> <li><a href="/wiki/Lead_poisoning" title="Lead poisoning">Lead</a></li> <li><a href="/wiki/Mercury_poisoning" title="Mercury poisoning">Mercury</a></li> <li><a href="/wiki/Nickel#Toxicity" title="Nickel">Nickel</a></li> <li><a href="/wiki/Thallium_poisoning" title="Thallium poisoning">Thallium</a></li> <li><a href="/wiki/Tin_poisoning" title="Tin poisoning">Tin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dietary_mineral" class="mw-redirect" title="Dietary mineral">Dietary minerals</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/Chromium_toxicity" title="Chromium toxicity">Chromium</a></li> <li><a href="/wiki/Cobalt_poisoning" title="Cobalt poisoning">Cobalt</a></li> <li><a href="/wiki/Copper_toxicity" title="Copper toxicity">Copper</a></li> <li><a href="/wiki/Iron_poisoning" title="Iron poisoning">Iron</a></li> <li><a href="/wiki/Manganism" title="Manganism">Manganese</a></li> <li><a href="/wiki/Zinc_toxicity" title="Zinc toxicity">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other non-toxic metals</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/Argyria" title="Argyria">Silver</a><sup>1</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metalloid" title="Metalloid">Metalloids</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/Arsenic_poisoning" title="Arsenic poisoning">Arsenic</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nonmetal_(chemistry)" class="mw-redirect" title="Nonmetal (chemistry)">Nonmetals</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/Sulfuric_acid_poisoning" title="Sulfuric acid poisoning">Sulfuric acid</a></li> <li><a href="/wiki/Selenium#Toxicity" title="Selenium">Selenium</a></li> <li><a href="/wiki/Chlorine_gas_poisoning" title="Chlorine gas poisoning">Chlorine</a></li> <li><a href="/wiki/Fluoride_toxicity" title="Fluoride toxicity">Fluoride</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_compound" title="Organic compound">Organic</a></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/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/Pesticide_poisoning" title="Pesticide poisoning">Pesticides</a> <ul><li><a href="/wiki/Aluminium_phosphide_poisoning" title="Aluminium phosphide poisoning">Aluminium phosphide</a></li> <li><a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">Organophosphates</a></li></ul></li></ul> </div></td></tr><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/Cyanide_poisoning" title="Cyanide poisoning">Cyanide</a></li> <li><a href="/wiki/Nicotine_poisoning" title="Nicotine poisoning">Nicotine</a></li> <li><a href="/wiki/Nitrogen_dioxide_poisoning" title="Nitrogen dioxide poisoning">Nitrogen dioxide poisoning</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">CHO</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a class="mw-selflink selflink">alcohol</a></i> <ul><li><a href="/wiki/Short-term_effects_of_alcohol_consumption#Excessive_doses" title="Short-term effects of alcohol consumption">Ethanol</a></li> <li><a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">Ethylene glycol</a></li> <li><a href="/wiki/Methanol_toxicity" title="Methanol toxicity">Methanol</a></li></ul></li> <li><a href="/wiki/Carbon_monoxide_poisoning" title="Carbon monoxide poisoning">Carbon monoxide</a></li> <li><a href="/wiki/Oxygen_toxicity" title="Oxygen toxicity">Oxygen</a></li> <li><a href="/wiki/Toluene_toxicity" title="Toluene toxicity">Toluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">Pharmaceutical</a></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 id="Drug_overdoses" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Drug_overdose" title="Drug overdose">Drug overdoses</a></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/Nervous_system" title="Nervous system">Nervous</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/Alcohol_intoxication" title="Alcohol intoxication">Alcohol</a></li> <li><a href="/wiki/Anticholinesterase_poisoning" class="mw-redirect" title="Anticholinesterase poisoning">Anticholinesterase</a></li> <li><a href="/wiki/Aspirin_poisoning" class="mw-redirect" title="Aspirin poisoning">Aspirin</a></li> <li><a href="/wiki/Barbiturate_overdose" title="Barbiturate overdose">Barbiturates</a></li> <li><a href="/wiki/Benzodiazepine_overdose" title="Benzodiazepine overdose">Benzodiazepines</a></li> <li><a href="/wiki/Cocaine_toxicity" class="mw-redirect" title="Cocaine toxicity">Cocaine</a></li> <li><a href="/wiki/Lithium_toxicity" title="Lithium toxicity">Lithium</a></li> <li><a href="/wiki/Opioid_overdose" title="Opioid overdose">Opioids</a></li> <li><a href="/wiki/Paracetamol_poisoning" title="Paracetamol poisoning">Paracetamol</a></li> <li><a href="/wiki/Serotonin_syndrome" title="Serotonin syndrome">Serotonergic substances</a></li> <li><a href="/wiki/Tricyclic_antidepressant_overdose" title="Tricyclic antidepressant overdose">Tricyclic antidepressants</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">Cardiovascular</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/Digoxin_toxicity" title="Digoxin toxicity">Digoxin</a></li> <li><a href="/wiki/Dipyridamole#Overdose" title="Dipyridamole">Dipyridamole</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_poisoning" class="mw-redirect" title="Vitamin poisoning">Vitamin poisoning</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/Hypervitaminosis_A" title="Hypervitaminosis A">Vitamin A</a></li> <li><a href="/wiki/Hypervitaminosis_D" class="mw-redirect" title="Hypervitaminosis D">Vitamin D</a></li> <li><a href="/wiki/Hypervitaminosis_E" class="mw-redirect" title="Hypervitaminosis E">Vitamin E</a></li> <li><a href="/wiki/Megavitamin-B6_syndrome" title="Megavitamin-B6 syndrome">Megavitamin-B<sub>6</sub> syndrome</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Biological<sup>2</sup></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/Venomous_fish" title="Venomous fish">Fish</a> / <a href="/wiki/Seafood" title="Seafood">Seafood</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/Ciguatera" class="mw-redirect" title="Ciguatera">Ciguatera</a></li> <li><a href="/wiki/Haff_disease" title="Haff disease">Haff disease</a></li> <li><a href="/wiki/Ichthyoallyeinotoxism" title="Ichthyoallyeinotoxism">Ichthyoallyeinotoxism</a></li> <li><a href="/wiki/Scombroid_food_poisoning" title="Scombroid food poisoning">Scombroid</a></li> <li><a href="/wiki/Shellfish_poisoning" title="Shellfish poisoning">Shellfish poisoning</a> <ul><li><a href="/wiki/Amnesic_shellfish_poisoning" title="Amnesic shellfish poisoning">Amnesic</a></li> <li><a href="/wiki/Diarrhetic_shellfish_poisoning" class="mw-redirect" title="Diarrhetic shellfish poisoning">Diarrhetic</a></li> <li><a href="/wiki/Neurotoxic_shellfish_poisoning" title="Neurotoxic shellfish poisoning">Neurotoxic</a></li> <li><a href="/wiki/Paralytic_shellfish_poisoning" title="Paralytic shellfish poisoning">Paralytic</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</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/Poisonous_amphibian" title="Poisonous amphibian">Amphibian</a> <ul><li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Bombesin" title="Bombesin">Bombesin</a></li> <li><a href="/wiki/Bufotenin" title="Bufotenin">Bufotenin</a></li> <li><a href="/wiki/Physalaemin" title="Physalaemin">Physalaemin</a></li></ul></li> <li><a href="/wiki/Toxic_bird" title="Toxic bird">Birds</a> <ul><li><a href="/wiki/Coturnism" title="Coturnism">Coturnism</a></li></ul></li> <li><a href="/wiki/Venomous_mammal" title="Venomous mammal">Mammal</a></li> <li><a href="/wiki/Venomous_snake" title="Venomous snake">Snakes</a> / <a href="/wiki/Snake_venom" title="Snake venom">Snake venom</a> <ul><li><a href="/wiki/Alpha-Bungarotoxin" class="mw-redirect" title="Alpha-Bungarotoxin">Alpha-Bungarotoxin</a></li> <li><a href="/wiki/Ancrod" title="Ancrod">Ancrod</a></li> <li><a href="/wiki/Batroxobin" title="Batroxobin">Batroxobin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arthropod" title="Arthropod">Arthropods</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/Arthropod_bites_and_stings" title="Arthropod bites and stings">Arthropod bites and stings</a></li> <li><a href="/wiki/Bee_sting" title="Bee sting">Bee sting</a> / <a href="/wiki/Apitoxin" title="Apitoxin">Bee venom</a> <ul><li><a href="/wiki/Apamin" title="Apamin">Apamin</a></li> <li><a href="/wiki/Melittin" title="Melittin">Melittin</a></li></ul></li> <li><a href="/wiki/Scorpion_venom" class="mw-redirect" title="Scorpion venom">Scorpion venom</a> <ul><li><a href="/wiki/Charybdotoxin" title="Charybdotoxin">Charybdotoxin</a></li></ul></li> <li><a href="/wiki/Spider_bite" title="Spider bite">spider venom</a> <ul><li><a href="/wiki/Latrotoxin" title="Latrotoxin">Latrotoxin</a> / <a href="/wiki/Latrodectism" title="Latrodectism">Latrodectism</a></li> <li><a href="/wiki/Loxoscelism" title="Loxoscelism">Loxoscelism</a></li></ul></li> <li><a href="/wiki/Tick_paralysis" title="Tick paralysis">Tick paralysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_poisonous_plants" title="List of poisonous plants">Plants</a> / <a href="/wiki/List_of_poisonous_fungus_species" title="List of poisonous fungus species">Fungi</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/Cinchonism" title="Cinchonism">Cinchonism</a></li> <li><a href="/wiki/Ergotism" title="Ergotism">Ergotism</a></li> <li><a href="/wiki/Fish_toxins" title="Fish toxins">Fish toxins</a></li> <li><a href="/wiki/Lathyrism" title="Lathyrism">Lathyrism</a></li> <li><a href="/wiki/Locoweed" title="Locoweed">Locoism</a></li> <li><a href="/wiki/Mushroom_poisoning" title="Mushroom poisoning">Mushroom</a></li> <li><a href="/wiki/Strychnine_poisoning" title="Strychnine poisoning">Strychnine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</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/Animal_bite" title="Animal bite">Bite</a> and <a href="/wiki/Stinger" title="Stinger">Stinger</a> <ul><li><a href="/wiki/Stinging_plant" title="Stinging plant">plant</a></li></ul></li> <li><a href="/wiki/Cnidocyte" title="Cnidocyte">Cnidocyte</a></li> <li><a href="/wiki/List_of_venomous_animals" title="List of venomous animals">Venomous animals</a></li> <li><a href="/wiki/List_of_poisonous_animals" title="List of poisonous animals">Poisonous animals</a></li> <li><a href="/wiki/List_of_deadly_fungus_species" title="List of deadly fungus species">Deadly fungus</a></li> <li><a href="/wiki/Mycotoxicology" title="Mycotoxicology">Mycotoxicology</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Miscellaneous</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/Antibiotic" title="Antibiotic">Antibiotic</a></li> <li><a href="/wiki/EPA_list_of_extremely_hazardous_substances" title="EPA list of extremely hazardous substances">EPA list of hazard</a></li> <li><a href="/wiki/Lists_of_poisonings" title="Lists of poisonings">Lists of poisonings</a></li> <li><a href="/wiki/List_of_types_of_poison" title="List of types of poison">List of types of poison</a></li> <li><a href="/wiki/Pollution" title="Pollution">Pollution</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td class="navbox-abovebelow" colspan="2"><div id="1Silver_is_generally_non-toxic_metal,_but_in_large_doses_it_can_lead_to_argyria,_which_is_rare._2_including_venoms,_toxins,_foodborne_illnesses."><sup>1</sup><a href="/wiki/Silver" title="Silver">Silver</a> is generally non-toxic metal, but in large doses it can lead to <a href="/wiki/Argyria" title="Argyria">argyria</a>, which is rare.<br /> <sup>2</sup> including <a href="/wiki/Venom" title="Venom">venoms</a>, <a href="/wiki/Toxin" title="Toxin">toxins</a>, <a href="/wiki/Foodborne_illness" title="Foodborne illness">foodborne illnesses</a>.</div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" 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id="Organic_chemistry_affixes" style="font-size:114%;margin:0 4em"><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">Organic chemistry affixes</a><div style="clear:both;" class=""></div></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbon" title="Carbon">Carbon</a>-based</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ane" title="-ane">-ane</a> (<a href="/wiki/Alkane" title="Alkane">alkane</a>)</li> <li><a href="/wiki/-ene" title="-ene">-ene</a> (<a href="/wiki/Alkene" title="Alkene">alkene</a>)</li> <li><a href="/wiki/-ine" title="-ine">-ine</a> (unsaturated <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>)</li> <li><a href="/wiki/-yne" title="-yne">-yne</a> (<a href="/wiki/Alkyne" title="Alkyne">alkyne</a>)</li> <li><a href="/wiki/Alk-" title="Alk-">alk-</a> (nonaromatic <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>)</li> <li><a href="https://en.wiktionary.org/wiki/ar-" class="extiw" title="wiktionary:ar-">ar-</a> (<a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a>)</li> <li><a href="/wiki/Cyclo-" class="mw-redirect" title="Cyclo-">cyclo-</a> (<a href="/wiki/Alicyclic_compound" title="Alicyclic compound">cyclic</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-al" title="-al">-al</a> (<a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>)</li> <li><a href="/wiki/-oate" title="-oate">-oate</a> (<a href="/wiki/Ester" title="Ester">ester</a>)</li> <li><a href="/wiki/-oic_acid" class="mw-redirect" title="-oic acid">-oic acid</a> (<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>)</li> <li><a href="/wiki/-ol" title="-ol">-ol</a> (<a class="mw-selflink selflink">alcohol</a>)</li> <li><a href="/wiki/-one" title="-one">-one</a> (<a href="/wiki/Ketone" title="Ketone">ketone</a>)</li> <li><a href="/wiki/-ose" title="-ose">-ose</a> (<a href="/wiki/Sugar" title="Sugar">sugar</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a>-based</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ine" title="-ine">-ine</a> (<a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>)</li> <li><a href="/wiki/Aza-" title="Aza-">aza-</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a> replaces <a href="/wiki/Carbon" title="Carbon">C</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thio-" title="Thio-">thio-</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a> replaces <a href="/wiki/Oxygen" title="Oxygen">O</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Counting axial atoms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Meth-" class="mw-redirect" title="Meth-">meth-</a> (1)</li> <li><a href="/wiki/Eth-" class="mw-redirect" title="Eth-">eth-</a> (2)</li> <li><a href="/wiki/Prop-" class="mw-redirect" title="Prop-">prop-</a> (3)</li> <li><a href="/wiki/But-" class="mw-redirect" title="But-">but-</a> (4)</li> <li>(and the rest are <a href="/wiki/Numeral_prefix#Greek_series" title="Numeral prefix">ordinary Greek/Latin prefixes</a>)</li></ul> 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