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Alkohol - Wikipedija, prosta enciklopedija

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<div class="vector-menu-heading"> Navigacija </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage" class="mw-list-item"><a href="/wiki/Glavna_stran" title="Obiščite glavno stran [z]" accesskey="z"><span>Glavna stran</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Pomo%C4%8D:Uvod"><span>Naučite se urejati</span></a></li><li id="n-Izbrani-članki" class="mw-list-item"><a href="/wiki/Wikipedija:Izbrani_%C4%8Dlanki"><span>Izbrani članki</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Posebno:Naklju%C4%8Dno" title="Naložite naključno stran [x]" accesskey="x"><span>Naključna stran</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Posebno:ZadnjeSpremembe" title="Seznam zadnjih sprememb Wikipedije [r]" accesskey="r"><span>Zadnje spremembe</span></a></li> </ul> </div> </div> <div id="p-obcestvo" class="vector-menu mw-portlet mw-portlet-obcestvo" > <div class="vector-menu-heading"> Skupnost </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Pomo%C4%8D:Vsebina" title="Kraj, kjer lahko prejmete pomoč"><span>Pomoč</span></a></li><li id="n-Pod-lipo" class="mw-list-item"><a href="/wiki/Wikipedija:Pod_lipo"><span>Pod lipo</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedija:Portal_skupnosti" title="O projektu, kaj lahko storite, kje lahko kaj najdete"><span>Portal skupnosti</span></a></li><li id="n-contact" class="mw-list-item"><a href="/wiki/Wikipedija:Stik_z_nami"><span>Stik z nami</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Glavna_stran" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedija" src="/static/images/mobile/copyright/wikipedia-wordmark-sl.svg" style="width: 7.4375em; height: 1.375em;"> <img class="mw-logo-tagline" alt="prosta enciklopedija" src="/static/images/mobile/copyright/wikipedia-tagline-sl.svg" width="118" height="13" style="width: 7.375em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Posebno:Iskanje" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Preiščite viki [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Iskanje</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> 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</ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Videz"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page&#039;s font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Videz" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-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-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Videz</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&amp;utm_medium=sidebar&amp;utm_campaign=C13_sl.wikipedia.org&amp;uselang=sl" class=""><span>Denarni prispevki</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Posebno:Registracija&amp;returnto=Alkohol" title="Predlagamo vam, da si ustvarite račun in se prijavite, vendar to ni obvezno." class=""><span>Ustvari račun</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Posebno:Prijava&amp;returnto=Alkohol" title="Prijava je zaželena, vendar ni obvezna [o]" accesskey="o" class=""><span>Prijava</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Več možnosti" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Osebna orodja" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-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-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Osebna orodja</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="Uporabniški meni" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&amp;utm_medium=sidebar&amp;utm_campaign=C13_sl.wikipedia.org&amp;uselang=sl"><span>Denarni prispevki</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Posebno:Registracija&amp;returnto=Alkohol" title="Predlagamo vam, da si ustvarite račun in se prijavite, vendar to ni obvezno."><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Ustvari račun</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Posebno:Prijava&amp;returnto=Alkohol" title="Prijava je zaželena, vendar ni obvezna [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Prijava</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Strani za neprijavljene urejevalce <a href="/wiki/Pomo%C4%8D:Uvod" aria-label="Več o urejanju"><span>več o tem</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Posebno:MojiPrispevki" title="Seznam urejanj s tega IP-naslova [y]" accesskey="y"><span>Prispevki</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Posebno:MojPogovor" title="Pogovor o urejanjih s tega IP-naslova [n]" accesskey="n"><span>Pogovorna stran</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"><!-- CentralNotice --></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Projekt"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Vsebina" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Vsebina</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">prestavi v stransko letvico</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">skrij</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Uvod</div> </a> </li> <li id="toc-Enostavni_alkoholi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Enostavni_alkoholi"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Enostavni alkoholi</span> </div> </a> <ul id="toc-Enostavni_alkoholi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenklatura" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenklatura"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Nomenklatura</span> </div> </a> <button aria-controls="toc-Nomenklatura-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>Vklopi podrazdelek Nomenklatura</span> </button> <ul id="toc-Nomenklatura-sublist" class="vector-toc-list"> <li id="toc-IUPAC" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#IUPAC"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>IUPAC</span> </div> </a> <ul id="toc-IUPAC-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Druga_imena" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Druga_imena"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Druga imena</span> </div> </a> <ul id="toc-Druga_imena-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Fizikalne_in_kemijske_lastnosti" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Fizikalne_in_kemijske_lastnosti"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Fizikalne in kemijske lastnosti</span> </div> </a> <ul id="toc-Fizikalne_in_kemijske_lastnosti-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uporaba" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uporaba"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Uporaba</span> </div> </a> <ul id="toc-Uporaba-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Proizvodnja" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Proizvodnja"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Proizvodnja</span> </div> </a> <button aria-controls="toc-Proizvodnja-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>Vklopi podrazdelek Proizvodnja</span> </button> <ul id="toc-Proizvodnja-sublist" class="vector-toc-list"> <li id="toc-Endogeni_etanol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Endogeni_etanol"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Endogeni etanol</span> </div> </a> <ul id="toc-Endogeni_etanol-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Laboratorijska_sinteza" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Laboratorijska_sinteza"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Laboratorijska sinteza</span> </div> </a> <ul id="toc-Laboratorijska_sinteza-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reakcije" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reakcije"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Reakcije</span> </div> </a> <button aria-controls="toc-Reakcije-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>Vklopi podrazdelek Reakcije</span> </button> <ul id="toc-Reakcije-sublist" class="vector-toc-list"> <li id="toc-Protoliza" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protoliza"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Protoliza</span> </div> </a> <ul id="toc-Protoliza-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nukleofilna_substitucija" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nukleofilna_substitucija"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Nukleofilna substitucija</span> </div> </a> <ul id="toc-Nukleofilna_substitucija-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Eliminacija_vode_(dehidracija)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Eliminacija_vode_(dehidracija)"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Eliminacija vode (dehidracija)</span> </div> </a> <ul id="toc-Eliminacija_vode_(dehidracija)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Estrenje" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Estrenje"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Estrenje</span> </div> </a> <ul id="toc-Estrenje-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oksidacija" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oksidacija"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.5</span> <span>Oksidacija</span> </div> </a> <ul id="toc-Oksidacija-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toksičnost" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toksičnost"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.6</span> <span>Toksičnost</span> </div> </a> <ul id="toc-Toksičnost-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reference" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reference"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Reference</span> </div> </a> <ul id="toc-Reference-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Glej_tudi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glej_tudi"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Glej tudi</span> </div> </a> <ul id="toc-Glej_tudi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Zunanje_povezave" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Zunanje_povezave"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Zunanje povezave</span> </div> </a> <ul id="toc-Zunanje_povezave-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="Vsebina" 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="Vklopi kazalo vsebine" > <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">Vklopi kazalo vsebine</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">Alkohol</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="P9jdi na članek v drugem jeziku. Na voljo v 130 jezikih." > <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 jezikov</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 – afrikanščina" lang="af" hreflang="af" data-title="Alkohol" data-language-autonym="Afrikaans" data-language-local-name="afrikanščina" 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 – nemščina (Švica)" lang="gsw" hreflang="gsw" data-title="Alkohole" data-language-autonym="Alemannisch" data-language-local-name="nemščina (Švica)" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Alcol" title="Alcol – aragonščina" lang="an" hreflang="an" data-title="Alcol" data-language-autonym="Aragonés" data-language-local-name="aragonščina" class="interlanguage-link-target"><span>Aragonés</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 – angikaščina" lang="anp" hreflang="anp" data-title="ऐल्कोहॉल" data-language-autonym="अंगिका" data-language-local-name="angikaščina" 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 – arabščina" lang="ar" hreflang="ar" data-title="كحول" data-language-autonym="العربية" data-language-local-name="arabščina" class="interlanguage-link-target"><span>العربية</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-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&#039;হল – asamščina" lang="as" hreflang="as" data-title="এলক&#039;হল" data-language-autonym="অসমীয়া" data-language-local-name="asamščina" 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 – asturijščina" lang="ast" hreflang="ast" data-title="Alcohol" data-language-autonym="Asturianu" data-language-local-name="asturijščina" 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 – avadščina" lang="awa" hreflang="awa" data-title="अल्कोहल" data-language-autonym="अवधी" data-language-local-name="avadščina" 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 – azerbajdžanščina" lang="az" hreflang="az" data-title="Spirtlər" data-language-autonym="Azərbaycanca" data-language-local-name="azerbajdžanščina" 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-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82" title="Спирт – baškirščina" lang="ba" hreflang="ba" data-title="Спирт" data-language-autonym="Башҡортса" data-language-local-name="baškirščina" class="interlanguage-link-target"><span>Башҡортса</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-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-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 – beloruščina" lang="be" hreflang="be" data-title="Спірты" data-language-autonym="Беларуская" data-language-local-name="beloruščina" 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-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 – bolgarščina" lang="bg" hreflang="bg" data-title="Алкохол" data-language-autonym="Български" data-language-local-name="bolgarščina" class="interlanguage-link-target"><span>Български</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 – bengalščina" lang="bn" hreflang="bn" data-title="অ্যালকোহল" data-language-autonym="বাংলা" data-language-local-name="bengalščina" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Alkool_(kimiezh)" title="Alkool (kimiezh) – bretonščina" lang="br" hreflang="br" data-title="Alkool (kimiezh)" data-language-autonym="Brezhoneg" data-language-local-name="bretonščina" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Alkohol" title="Alkohol – bosanščina" lang="bs" hreflang="bs" data-title="Alkohol" data-language-autonym="Bosanski" data-language-local-name="bosanščina" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Alcohol" title="Alcohol – katalonščina" lang="ca" hreflang="ca" data-title="Alcohol" data-language-autonym="Català" data-language-local-name="katalonščina" class="interlanguage-link-target"><span>Català</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 – osrednja kurdščina" lang="ckb" hreflang="ckb" data-title="ئەلکھول" data-language-autonym="کوردی" data-language-local-name="osrednja kurdščina" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Alkoholy" title="Alkoholy – češčina" lang="cs" hreflang="cs" data-title="Alkoholy" data-language-autonym="Čeština" data-language-local-name="češčina" 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 – valižanščina" lang="cy" hreflang="cy" data-title="Alcohol" data-language-autonym="Cymraeg" data-language-local-name="valižanščina" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alkohol_(stofklasse)" title="Alkohol (stofklasse) – danščina" lang="da" hreflang="da" data-title="Alkohol (stofklasse)" data-language-autonym="Dansk" data-language-local-name="danščina" class="interlanguage-link-target"><span>Dansk</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-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Alkohole" title="Alkohole – nemščina" lang="de" hreflang="de" data-title="Alkohole" data-language-autonym="Deutsch" data-language-local-name="nemščina" class="interlanguage-link-target"><span>Deutsch</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 – grščina" lang="el" hreflang="el" data-title="Αλκοόλες" data-language-autonym="Ελληνικά" data-language-local-name="grščina" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry) – angleščina" lang="en" hreflang="en" data-title="Alcohol (chemistry)" data-language-autonym="English" data-language-local-name="angleščina" class="interlanguage-link-target"><span>English</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-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alcohol" title="Alcohol – španščina" lang="es" hreflang="es" data-title="Alcohol" data-language-autonym="Español" data-language-local-name="španščina" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alkoholid" title="Alkoholid – estonščina" lang="et" hreflang="et" data-title="Alkoholid" data-language-autonym="Eesti" data-language-local-name="estonščina" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Alkohol" title="Alkohol – baskovščina" lang="eu" hreflang="eu" data-title="Alkohol" data-language-autonym="Euskara" data-language-local-name="baskovščina" 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 – perzijščina" lang="fa" hreflang="fa" data-title="الکل" data-language-autonym="فارسی" data-language-local-name="perzijščina" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Alkoholit" title="Alkoholit – finščina" lang="fi" hreflang="fi" data-title="Alkoholit" data-language-autonym="Suomi" data-language-local-name="finščina" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Alkohol" title="Alkohol – ferščina" lang="fo" hreflang="fo" data-title="Alkohol" data-language-autonym="Føroyskt" data-language-local-name="ferščina" 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) – francoščina" lang="fr" hreflang="fr" data-title="Alcool (chimie)" data-language-autonym="Français" data-language-local-name="francoščina" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Alkohol" title="Alkohol – severna frizijščina" lang="frr" hreflang="frr" data-title="Alkohol" data-language-autonym="Nordfriisk" data-language-local-name="severna frizijščina" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Alc%C3%B3il" title="Alcóil – irščina" lang="ga" hreflang="ga" data-title="Alcóil" data-language-autonym="Gaeilge" data-language-local-name="irščina" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gd mw-list-item"><a href="https://gd.wikipedia.org/wiki/Alcol" title="Alcol – škotska gelščina" lang="gd" hreflang="gd" data-title="Alcol" data-language-autonym="Gàidhlig" data-language-local-name="škotska gelščina" 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 – galicijščina" lang="gl" hreflang="gl" data-title="Alcohol" data-language-autonym="Galego" data-language-local-name="galicijščina" 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 – gudžaratščina" lang="gu" hreflang="gu" data-title="આલ્કોહોલ" data-language-autonym="ગુજરાતી" data-language-local-name="gudžaratščina" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-gv mw-list-item"><a href="https://gv.wikipedia.org/wiki/Alcoal" title="Alcoal – manščina" lang="gv" hreflang="gv" data-title="Alcoal" data-language-autonym="Gaelg" data-language-local-name="manščina" class="interlanguage-link-target"><span>Gaelg</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 – hebrejščina" lang="he" hreflang="he" data-title="כוהל" data-language-autonym="עברית" data-language-local-name="hebrejščina" class="interlanguage-link-target"><span>עברית</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 – hindijščina" lang="hi" hreflang="hi" data-title="ऐल्कोहॉल" data-language-autonym="हिन्दी" data-language-local-name="hindijščina" class="interlanguage-link-target"><span>हिन्दी</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-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alkoholi" title="Alkoholi – hrvaščina" lang="hr" hreflang="hr" data-title="Alkoholi" data-language-autonym="Hrvatski" data-language-local-name="hrvaščina" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Alk%C3%B2l" title="Alkòl – haitijska kreolščina" lang="ht" hreflang="ht" data-title="Alkòl" data-language-autonym="Kreyòl ayisyen" data-language-local-name="haitijska kreolščina" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alkoholok" title="Alkoholok – madžarščina" lang="hu" hreflang="hu" data-title="Alkoholok" data-language-autonym="Magyar" data-language-local-name="madžarščina" class="interlanguage-link-target"><span>Magyar</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 – armenščina" lang="hy" hreflang="hy" data-title="Սպիրտ" data-language-autonym="Հայերեն" data-language-local-name="armenščina" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Alcohol" title="Alcohol – interlingva" lang="ia" hreflang="ia" data-title="Alcohol" data-language-autonym="Interlingua" data-language-local-name="interlingva" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkohol" title="Alkohol – indonezijščina" lang="id" hreflang="id" data-title="Alkohol" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonezijščina" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ilo mw-list-item"><a href="https://ilo.wikipedia.org/wiki/Alkohol" title="Alkohol – ilokanščina" lang="ilo" hreflang="ilo" data-title="Alkohol" data-language-autonym="Ilokano" data-language-local-name="ilokanščina" class="interlanguage-link-target"><span>Ilokano</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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Alk%C3%B3h%C3%B3l" title="Alkóhól – islandščina" lang="is" hreflang="is" data-title="Alkóhól" data-language-autonym="Íslenska" data-language-local-name="islandščina" 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 – italijanščina" lang="it" hreflang="it" data-title="Alcoli" data-language-autonym="Italiano" data-language-local-name="italijanščina" class="interlanguage-link-target"><span>Italiano</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 – japonščina" lang="ja" hreflang="ja" data-title="アルコール" data-language-autonym="日本語" data-language-local-name="japonščina" class="interlanguage-link-target"><span>日本語</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-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Alkohol" title="Alkohol – javanščina" lang="jv" hreflang="jv" data-title="Alkohol" data-language-autonym="Jawa" data-language-local-name="javanščina" class="interlanguage-link-target"><span>Jawa</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 – gruzijščina" lang="ka" hreflang="ka" data-title="სპირტი" data-language-autonym="ქართული" data-language-local-name="gruzijščina" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/I%C9%A3isem" title="Iɣisem – kabilščina" lang="kab" hreflang="kab" data-title="Iɣisem" data-language-autonym="Taqbaylit" data-language-local-name="kabilščina" class="interlanguage-link-target"><span>Taqbaylit</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-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><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 – kazaščina" lang="kk" hreflang="kk" data-title="Алкогольдер" data-language-autonym="Қазақша" data-language-local-name="kazaščina" class="interlanguage-link-target"><span>Қазақша</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 – kanareščina" lang="kn" hreflang="kn" data-title="ಆಲ್ಕೋಹಾಲ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="kanareščina" class="interlanguage-link-target"><span>ಕನ್ನಡ</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 – korejščina" lang="ko" hreflang="ko" data-title="알코올" data-language-autonym="한국어" data-language-local-name="korejščina" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ksh mw-list-item"><a href="https://ksh.wikipedia.org/wiki/Alkohol" title="Alkohol – kölnsko narečje" lang="ksh" hreflang="ksh" data-title="Alkohol" data-language-autonym="Ripoarisch" data-language-local-name="kölnsko narečje" class="interlanguage-link-target"><span>Ripoarisch</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Alkol" title="Alkol – kurdščina" lang="ku" hreflang="ku" data-title="Alkol" data-language-autonym="Kurdî" data-language-local-name="kurdščina" 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 – kirgiščina" lang="ky" hreflang="ky" data-title="Спирт" data-language-autonym="Кыргызча" data-language-local-name="kirgiščina" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Alcohol" title="Alcohol – latinščina" lang="la" hreflang="la" data-title="Alcohol" data-language-autonym="Latina" data-language-local-name="latinščina" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lad mw-list-item"><a href="https://lad.wikipedia.org/wiki/Alk%C3%B3l" title="Alkól – ladinščina" lang="lad" hreflang="lad" data-title="Alkól" data-language-autonym="Ladino" data-language-local-name="ladinščina" class="interlanguage-link-target"><span>Ladino</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Alkoholen" title="Alkoholen – luksemburščina" lang="lb" hreflang="lb" data-title="Alkoholen" data-language-autonym="Lëtzebuergesch" data-language-local-name="luksemburščina" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Alcohol" title="Alcohol – limburščina" lang="li" hreflang="li" data-title="Alcohol" data-language-autonym="Limburgs" data-language-local-name="limburščina" class="interlanguage-link-target"><span>Limburgs</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-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-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-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkoholis" title="Alkoholis – litovščina" lang="lt" hreflang="lt" data-title="Alkoholis" data-language-autonym="Lietuvių" data-language-local-name="litovščina" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Spirti" title="Spirti – latvijščina" lang="lv" hreflang="lv" data-title="Spirti" data-language-autonym="Latviešu" data-language-local-name="latvijščina" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Alikaola_(simia)" title="Alikaola (simia) – malgaščina" lang="mg" hreflang="mg" data-title="Alikaola (simia)" data-language-autonym="Malagasy" data-language-local-name="malgaščina" class="interlanguage-link-target"><span>Malagasy</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-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 – makedonščina" lang="mk" hreflang="mk" data-title="Алкохол" data-language-autonym="Македонски" data-language-local-name="makedonščina" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%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) – malajalamščina" lang="ml" hreflang="ml" data-title="ചാരായം (രസതന്ത്രം)" data-language-autonym="മലയാളം" data-language-local-name="malajalamščina" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alkohol" title="Alkohol – malajščina" lang="ms" hreflang="ms" data-title="Alkohol" data-language-autonym="Bahasa Melayu" data-language-local-name="malajščina" class="interlanguage-link-target"><span>Bahasa Melayu</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 – burmanščina" lang="my" hreflang="my" data-title="အယ်လ်ကိုဟော" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="burmanščina" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Alkohol" title="Alkohol – nizka nemščina" lang="nds" hreflang="nds" data-title="Alkohol" data-language-autonym="Plattdüütsch" data-language-local-name="nizka nemščina" class="interlanguage-link-target"><span>Plattdüütsch</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 – nepalščina" lang="ne" hreflang="ne" data-title="अल्कोहल" data-language-autonym="नेपाली" data-language-local-name="nepalščina" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alcohol_(stofklasse)" title="Alcohol (stofklasse) – nizozemščina" lang="nl" hreflang="nl" data-title="Alcohol (stofklasse)" data-language-autonym="Nederlands" data-language-local-name="nizozemščina" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Alkoholar" title="Alkoholar – novonorveščina" lang="nn" hreflang="nn" data-title="Alkoholar" data-language-autonym="Norsk nynorsk" data-language-local-name="novonorveščina" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alkoholer" title="Alkoholer – knjižna norveščina" lang="nb" hreflang="nb" data-title="Alkoholer" data-language-autonym="Norsk bokmål" data-language-local-name="knjižna norveščina" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Alc%C3%B2l" title="Alcòl – okcitanščina" lang="oc" hreflang="oc" data-title="Alcòl" data-language-autonym="Occitan" data-language-local-name="okcitanščina" 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-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 – pandžabščina" lang="pa" hreflang="pa" data-title="ਅਲਕੋਹਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="pandžabščina" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkohole" title="Alkohole – poljščina" lang="pl" hreflang="pl" data-title="Alkohole" data-language-autonym="Polski" data-language-local-name="poljščina" class="interlanguage-link-target"><span>Polski</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 – paštunščina" lang="ps" hreflang="ps" data-title="الکول" data-language-autonym="پښتو" data-language-local-name="paštunščina" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81lcool" title="Álcool – portugalščina" lang="pt" hreflang="pt" data-title="Álcool" data-language-autonym="Português" data-language-local-name="portugalščina" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Alkul" title="Alkul – kečuanščina" lang="qu" hreflang="qu" data-title="Alkul" data-language-autonym="Runa Simi" data-language-local-name="kečuanščina" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Alcool" title="Alcool – romunščina" lang="ro" hreflang="ro" data-title="Alcool" data-language-autonym="Română" data-language-local-name="romunščina" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-roa-rup mw-list-item"><a href="https://roa-rup.wikipedia.org/wiki/Alcoolu" title="Alcoolu – aromunščina" lang="rup" hreflang="rup" data-title="Alcoolu" data-language-autonym="Armãneashti" data-language-local-name="aromunščina" class="interlanguage-link-target"><span>Armãneashti</span></a></li><li class="interlanguage-link interwiki-ru badge-Q17437796 badge-featuredarticle mw-list-item" title="izbrani članek"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D1%82%D1%8B" title="Спирты – ruščina" lang="ru" hreflang="ru" data-title="Спирты" data-language-autonym="Русский" data-language-local-name="ruščina" class="interlanguage-link-target"><span>Русский</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-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Alcool" title="Alcool – sicilijanščina" lang="scn" hreflang="scn" data-title="Alcool" data-language-autonym="Sicilianu" data-language-local-name="sicilijanščina" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Alcohol" title="Alcohol – škotščina" lang="sco" hreflang="sco" data-title="Alcohol" data-language-autonym="Scots" data-language-local-name="škotščina" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Alkoholi" title="Alkoholi – srbohrvaščina" lang="sh" hreflang="sh" data-title="Alkoholi" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="srbohrvaščina" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</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) – slovaščina" lang="sk" hreflang="sk" data-title="Alkohol (hydroxyderivát)" data-language-autonym="Slovenčina" data-language-local-name="slovaščina" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Alkooli" title="Alkooli – albanščina" lang="sq" hreflang="sq" data-title="Alkooli" data-language-autonym="Shqip" data-language-local-name="albanščina" class="interlanguage-link-target"><span>Shqip</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 – srbščina" lang="sr" hreflang="sr" data-title="Алкохол" data-language-autonym="Српски / srpski" data-language-local-name="srbščina" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alkohol" title="Alkohol – sundanščina" lang="su" hreflang="su" data-title="Alkohol" data-language-autonym="Sunda" data-language-local-name="sundanščina" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Alkoholer" title="Alkoholer – švedščina" lang="sv" hreflang="sv" data-title="Alkoholer" data-language-autonym="Svenska" data-language-local-name="švedščina" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Alkoholi" title="Alkoholi – svahili" lang="sw" hreflang="sw" data-title="Alkoholi" data-language-autonym="Kiswahili" data-language-local-name="svahili" class="interlanguage-link-target"><span>Kiswahili</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 – tamilščina" lang="ta" hreflang="ta" data-title="மதுசாரம்" data-language-autonym="தமிழ்" data-language-local-name="tamilščina" class="interlanguage-link-target"><span>தமிழ்</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 – telugijščina" lang="te" hreflang="te" data-title="ఆల్కహాలు" data-language-autonym="తెలుగు" data-language-local-name="telugijščina" 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 – tajščina" lang="th" hreflang="th" data-title="แอลกอฮอล์" data-language-autonym="ไทย" data-language-local-name="tajščina" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Alkohol" title="Alkohol – tagalogščina" lang="tl" hreflang="tl" data-title="Alkohol" data-language-autonym="Tagalog" data-language-local-name="tagalogščina" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alkol" title="Alkol – turščina" lang="tr" hreflang="tr" data-title="Alkol" data-language-autonym="Türkçe" data-language-local-name="turščina" class="interlanguage-link-target"><span>Türkçe</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 – tatarščina" lang="tt" hreflang="tt" data-title="Спиртлар" data-language-autonym="Татарча / tatarça" data-language-local-name="tatarščina" class="interlanguage-link-target"><span>Татарча / tatarça</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 – ukrajinščina" lang="uk" hreflang="uk" data-title="Спирти" data-language-autonym="Українська" data-language-local-name="ukrajinščina" 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 – urdujščina" lang="ur" hreflang="ur" data-title="الکحل" data-language-autonym="اردو" data-language-local-name="urdujščina" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Spirtlar" title="Spirtlar – uzbeščina" lang="uz" hreflang="uz" data-title="Spirtlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="uzbeščina" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Alcohol" title="Alcohol – vietnamščina" lang="vi" hreflang="vi" data-title="Alcohol" data-language-autonym="Tiếng Việt" data-language-local-name="vietnamščina" class="interlanguage-link-target"><span>Tiếng Việt</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 – varajščina" lang="war" hreflang="war" data-title="Arkohol" data-language-autonym="Winaray" data-language-local-name="varajščina" 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-kitajščina" lang="wuu" hreflang="wuu" data-title="醇" data-language-autonym="吴语" data-language-local-name="wu-kitajščina" 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 – jidiš" lang="yi" hreflang="yi" data-title="אלקאהאל" data-language-autonym="ייִדיש" data-language-local-name="jidiš" 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 – jorubščina" lang="yo" hreflang="yo" data-title="Ọtí" data-language-autonym="Yorùbá" data-language-local-name="jorubščina" class="interlanguage-link-target"><span>Yorùbá</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%86%87" title="醇 – kitajščina" lang="zh" hreflang="zh" data-title="醇" data-language-autonym="中文" data-language-local-name="kitajščina" class="interlanguage-link-target"><span>中文</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-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Alcohol" title="Alcohol – min nan kitajščina" lang="nan" hreflang="nan" data-title="Alcohol" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="min nan kitajščina" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</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 – kantonščina" lang="yue" hreflang="yue" data-title="酒精" data-language-autonym="粵語" data-language-local-name="kantonščina" class="interlanguage-link-target"><span>粵語</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q156#sitelinks-wikipedia" title="Uredi medjezikovne povezave" class="wbc-editpage">Uredi povezave</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Imenski prostori"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Alkohol" title="Ogled vsebinske strani [c]" accesskey="c"><span>Stran</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Ethanol-3D-vdW.png/330px-Ethanol-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Ethanol-3D-vdW.png/440px-Ethanol-3D-vdW.png 2x" data-file-width="1100" data-file-height="879" /></a><figcaption>Model molekule etanola.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/Slika:Alcohol_general.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Alcohol_general.svg/220px-Alcohol_general.svg.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Alcohol_general.svg/330px-Alcohol_general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Alcohol_general.svg/440px-Alcohol_general.svg.png 2x" data-file-width="115" data-file-height="68" /></a><figcaption>Funkcionalna skupina alkohola. Na ogljikov atom so lahko vezani trije vodikovi atomi ali ena, dve ali tri (lahko različne) alkilne skupine.</figcaption></figure> <p><b>Alkoholi</b> (iz <a href="/wiki/Arab%C5%A1%C4%8Dina" title="Arabščina">arabskega</a> الغول‎, al-ġuḥl) so <a href="/wiki/Organska_kemija" title="Organska kemija">organske</a> <a href="/wiki/Spojina" title="Spojina">spojine</a>, v katerih je hidroksilna skupina (–OH) vezana na <a href="/wiki/Ogljik" title="Ogljik">ogljikov</a> <a href="/wiki/Atom" title="Atom">atom</a> v alkilni ali substituirani alkilni skupini.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> Splošna formula enostavnih acikličnih alkoholov je <b>C<sub>n</sub>H<sub>2n+2</sub>O</b>. Alkoholi imajo po <a href="/wiki/Nomenklatura_organske_kemije_IUPAC" title="Nomenklatura organske kemije IUPAC">menklaturi IUPAC</a> končnico <b>–ol</b>. V vsakdanjem jeziku se beseda alkohol nanaša na etanol, ki je sestavina alkoholnih pijač. </p><p>Najbolj znan alkohol je <a href="/wiki/Etanol" title="Etanol">etanol</a>, ki je brezbarvna hlapna tekočina "pekočega" vonja in okusa, ki jo dobimo s <a href="/wiki/Fermentacija" title="Fermentacija">fermentacijo</a> <a href="/wiki/Sladkor" title="Sladkor">sladkorjev</a>. Industrijski sintetski etanol se pridobiva z adicijo vode na <a href="/wiki/Eten" title="Eten">eten</a> v pristonosti katalizatorja <a href="/wiki/Fosforna_kislina" class="mw-redirect" title="Fosforna kislina">fosforne kisline</a><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup>. Druga bolj znana alkohola sta <a href="/wiki/Metanol" title="Metanol">metanol</a>, ki je tudi sestavni del nekaterih alkoholnih pijač, in izopropil alkohol (propan-2-ol). </p><p>Alkoholi lahko vsebujejo tudi dve, tri ali več hidroksilnih skupin. Ti alkoholi se imenujejo dioli, trioli itd. Najbolj znan diol je <a href="/w/index.php?title=Glikol&amp;action=edit&amp;redlink=1" class="new" title="Glikol (stran ne obstaja)">glikol</a> (etan-1,2-diol), ki znižuje zmrzišče vode in se zato dodaja hladilnim tekočinam. Najbolj znan triol je <a href="/wiki/Glicerol" title="Glicerol">glicerol</a> (propan-1,2,3-triol), ki se uporablja v kozmetični industriji in <a href="/wiki/Industrija" class="mw-disambig" title="Industrija">industriji</a> <a href="/wiki/Eksploziv" title="Eksploziv">eksplozivov</a> (<a href="/w/index.php?title=Nitroglicerol&amp;action=edit&amp;redlink=1" class="new" title="Nitroglicerol (stran ne obstaja)">nitroglicerol</a>). </p><p>Alkohole razvrščamo v primarne, sekundarne in terciarne alkohole, odvisno od tega, ali imajo –OH skupino vezano na primarnem, sekundarnem ali terciarnem ogljikovem atomu. Primarni alkohol je na primer etanol, sekundarni propan-2-ol, terciarni pa 2-metilpropan-2-ol. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Enostavni_alkoholi">Enostavni alkoholi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=1" title="Uredi razdelek: Enostavni alkoholi" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=1" title="Urejanje izvorne kode razdelka: Enostavni alkoholi"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Najenostavnejša in najbolj znana alkohola sta metanol (CH<sub>3</sub>-OH) in etanol (C<sub>2</sub>H<sub>5</sub>-OH). Metanol so včasih pridobivali s suho destilacijo lesa in so ga zato imenovali lesni alkohol. Danes se na industrijski način pridobiva s <a href="/wiki/Katalizator" title="Katalizator">katalitskim</a> hidrogeniranjem <a href="/wiki/Ogljikov_monoksid" title="Ogljikov monoksid">ogljikovega monoksida</a> pri 250&#160;°C in pritisku 5-10 MPa: </p><p>CO + 2 H<sub>2</sub> → CH<sub>3</sub>OH </p><p>Metanol kot tak ni strupen. Strupena sta <a href="/wiki/Formaldehid" title="Formaldehid">metanal (formaldehid)</a> in <a href="/wiki/Metanojska_kislina" class="mw-redirect" title="Metanojska kislina">metanojska (mravljinčna) kislina</a>, ki nastaneta v <a href="/wiki/Jetra" title="Jetra">jetrih</a> pri presnovi metanola z alkoholnimi dehidrogenazami. Oba produkta uničujeta vidni živec in povzročata trajno slepoto<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> ali celo smrt. </p><p>Etanol je sestavina alkoholnih pijač, uporablja pa se tudi v zdravstvu, kot organsko topilo in industrijska surovina. Industrijski etanol je običajno denaturiran in zato strupen in neužiten. Od enostavnih alkoholov se uporabljata tudi propanol in butanol, ki se pridobivata s fermantacijo <a href="/wiki/Celuloza" title="Celuloza">celuloze</a> z <a href="/wiki/Bakterija" class="mw-redirect" title="Bakterija">bakterijo</a> <i>Clostridium acetobutylicum</i>. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenklatura">Nomenklatura</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=2" title="Uredi razdelek: Nomenklatura" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=2" title="Urejanje izvorne kode razdelka: Nomenklatura"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="IUPAC">IUPAC</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=3" title="Uredi razdelek: IUPAC" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=3" title="Urejanje izvorne kode razdelka: IUPAC"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><div class="noprint relarticle mainarticle"><i>Glavni članek&#58; <a href="/wiki/Nomenklatura_organske_kemije_IUPAC" title="Nomenklatura organske kemije IUPAC">Nomenklatura organske kemije IUPAC</a>.</i></div></dd></dl> <p>V sistemu IUPAC se imena alkoholov oblikujejo tako, da se imenom <a href="/wiki/Alkan" title="Alkan">alkanov</a> doda končnica –ol, na primer metan-ol in etan-ol.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> Kadar je treba, se imenu doda tudi številka ogljikovega atoma, na katerem je hidroksilna skupina, na primer: propan-1-ol za CH<sub>3</sub>-CH<sub>2</sub>-CH<sub>2</sub>-OH ali propan-2-ol za CH<sub>3</sub>-CH<sub>2</sub>(OH)-CH<sub>3</sub>. Včasih se položaj hidroksilne skupine zapiše tudi pred imenom spojine, na priemr 1-propanol ali 2-propanol. Če je v spojini funkcionalna skupina z višjo prioriteto, na primer v <a href="/wiki/Aldehid" title="Aldehid">aldehidih</a>, <a href="/wiki/Keton" title="Keton">ketonih</a> ali <a href="/wiki/Organska_kislina" class="mw-redirect" title="Organska kislina">karboksilnih kislinah</a>, dobi hidroksilna skupina predpono <i>hidroksi</i>, na primer 1-hidroksi-2-propanon (CH<sub>3</sub>-CO-CH<sub>2</sub>-OH). </p><p>Cilkični alkoholi imajo pred svojim imenom predpono <i>ciklo</i>, na primer ciklohehsanol. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/Slika:Alcohol_examples_sl.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Alcohol_examples_sl.png/600px-Alcohol_examples_sl.png" decoding="async" width="600" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/68/Alcohol_examples_sl.png 1.5x" data-file-width="760" data-file-height="253" /></a><figcaption>Nekateri alkoholi in njihova imena</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Druga_imena">Druga imena</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=4" title="Uredi razdelek: Druga imena" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=4" title="Urejanje izvorne kode razdelka: Druga imena"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Starejša imena alkoholov so običajno sestavljena iz imena alkilne skupine, kateri je dodana beseda <i>alkohol</i>, na primer metil alkohol ali etil alkohol. Propil alkohol je zaradi <a href="/wiki/Izomerija" class="mw-redirect" title="Izomerija">položajne izomerije</a> lahko n-propil alkohol ali izopropil alkohol, odvisno od tega, ali je –OH skupina na prvem ali drugem ogljikovem atomu. Izopropil alkohol se lahko imenuje tudi sekundarni propil alkohol, ker je –OH skupina na sekundarnem ogljikovem atomu. </p><p>Alkoholi se razvrščajo v primarne (1°), sekundarne (2°) in terciarne (3°) alkohole. V imenu alkohola je to zapisani pred imenom alkohola. Primer: terciarni alkohol (CH<sub>3</sub>)<sub>3</sub>C-OH, ki se po IUPAC nomenklaturi imenuje 2-metilpropan-2-ol, je terciarni alkohol, ki ga lahko imenujemo tudi terc-butil alkohol, ker ima štiri ogljikove atome. </p><p>Primarni alkoholi imajo splošno formulo R-CH<sub>2</sub>-OH, sekundarni RR'CH-OH, terciarni pa RR'R"C-OH. <a href="/wiki/Vodikova_vez" title="Vodikova vez">Vodikove vezi</a> so v primarnih alkoholih močnejše kot v sekundarnih in terciarnih alkoholih, zato imajo primarni alkoholi višja vrelišča in so bolj kisli. </p><p>Obstajajo tudi alkoholi z dvema, tremi ali več –OH skupinami, ki jih imenujemo dioli, trioli itd. Najbolj znan diol je <a href="/w/index.php?title=Glikol&amp;action=edit&amp;redlink=1" class="new" title="Glikol (stran ne obstaja)">glikol</a> (1,2-etandiol), ki je sestavina hladilne tekočine v avtomobilih in preprečuje zmrzovanje in <a href="/wiki/Glicerol" title="Glicerol">glicerol</a> (1,2,3-propantriol), ki se uporablja v kozmetični industriji in industriji eksplozivov. </p> <table class="wikitable" style="width:600px; white-space:nowrap; text-align:center;"> <tbody><tr> <th>&#160;Kemijska formula&#160; </th> <th>&#160;<a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> ime&#160; </th> <th>&#160;Drugo ime&#160; </th></tr> <tr> <td style="text-align:center;" colspan="3"><i>Monohidroksi alkoholi</i> </td></tr> <tr> <td>CH<sub>3</sub>OH </td> <td><a href="/wiki/Metanol" title="Metanol">metanol</a> </td> <td>lesni alkohol </td></tr> <tr> <td>C<sub>2</sub>H<sub>5</sub>OH </td> <td><a href="/wiki/Etanol" title="Etanol">etanol</a> </td> <td>etilni alkohol </td></tr> <tr> <td>C<sub>3</sub>H<sub>7</sub>OH </td> <td><a href="/w/index.php?title=Izopropilni_alkohol&amp;action=edit&amp;redlink=1" class="new" title="Izopropilni alkohol (stran ne obstaja)">izopropilni alkohol</a> </td> <td>čistilni alkohol </td></tr> <tr> <td>C<sub>4</sub>H<sub>9</sub>OH </td> <td><a href="/wiki/Butilni_alkohol" class="mw-redirect" title="Butilni alkohol">butilni alkohol</a> </td> <td>butanol </td></tr> <tr> <td>C<sub>5</sub>H<sub>11</sub>OH </td> <td>pentanol </td> <td><a href="/wiki/Amilni_alkohol" class="mw-redirect" title="Amilni alkohol">amilni alkohol</a> </td></tr> <tr> <td>C<sub>16</sub>H<sub>33</sub>OH </td> <td>heksadekan-1-ol </td> <td><a href="/w/index.php?title=Cetil_alkohol&amp;action=edit&amp;redlink=1" class="new" title="Cetil alkohol (stran ne obstaja)">cetil alkohol</a> </td></tr> <tr> <td style="text-align:center;" colspan="3"><i>Polihidridni alkoholi</i> </td></tr> <tr> <td>C<sub>2</sub>H<sub>4</sub>(OH)<sub>2</sub> </td> <td>etan-1,2-diol </td> <td><a href="/wiki/Etilenglikol" title="Etilenglikol">etilenglikol</a> </td></tr> <tr> <td>C<sub>3</sub>H<sub>6</sub>(OH)<sub>2</sub> </td> <td>propan-1,2-diol </td> <td><a href="/w/index.php?title=Propilenglikol&amp;action=edit&amp;redlink=1" class="new" title="Propilenglikol (stran ne obstaja)">propilenglikol</a> </td></tr> <tr> <td>C<sub>3</sub>H<sub>5</sub>(OH)<sub>3</sub> </td> <td>propan-1,2,3-triol </td> <td><a href="/wiki/Glicerol" title="Glicerol">glicerol</a> </td></tr> <tr> <td>C<sub>4</sub>H<sub>6</sub>(OH)<sub>4</sub> </td> <td>butan-1,2,3,4-tetraol </td> <td><a href="/wiki/Eritritol" title="Eritritol">eritritol</a>, <a href="/w/index.php?title=Treitol&amp;action=edit&amp;redlink=1" class="new" title="Treitol (stran ne obstaja)">treitol</a> </td></tr> <tr> <td>C<sub>5</sub>H<sub>7</sub>(OH)<sub>5</sub> </td> <td>pentan-1,2,3,4,5-pentol </td> <td><a href="/w/index.php?title=Ksilitol&amp;action=edit&amp;redlink=1" class="new" title="Ksilitol (stran ne obstaja)">ksilitol</a> </td></tr> <tr> <td>C<sub>6</sub>H<sub>8</sub>(OH)<sub>6</sub> </td> <td>heksan-1,2,3,4,5,6-heksol </td> <td><a href="/w/index.php?title=Manitol&amp;action=edit&amp;redlink=1" class="new" title="Manitol (stran ne obstaja)">manitol</a>, <a href="/wiki/Sorbitol" title="Sorbitol">sorbitol</a> </td></tr> <tr> <td>C<sub>7</sub>H<sub>9</sub>(OH)<sub>7</sub> </td> <td>heptan-1,2,3,4,5,6,7-heptol </td> <td><a href="/w/index.php?title=Volemitol&amp;action=edit&amp;redlink=1" class="new" title="Volemitol (stran ne obstaja)">volemitol</a> </td></tr> <tr> <td style="text-align:center;" colspan="3"><i>Nenasičeni <a href="/wiki/Alifatska_spojina" title="Alifatska spojina">alifatski</a> alkoholi</i> </td></tr> <tr> <td>C<sub>3</sub>H<sub>5</sub>OH </td> <td>Prop-2-ene-1-ol </td> <td><a href="/wiki/Alilalkohol" title="Alilalkohol">alilalkohol</a> </td></tr> <tr> <td>C<sub>10</sub>H<sub>17</sub>OH </td> <td>3,7-Dimethylocta-2,6-dien-1-ol </td> <td><a href="/w/index.php?title=Geraniol&amp;action=edit&amp;redlink=1" class="new" title="Geraniol (stran ne obstaja)">geraniol</a> </td></tr> <tr> <td>C<sub>3</sub>H<sub>3</sub>OH </td> <td>Prop-2-in-1-ol </td> <td><a href="/w/index.php?title=Propargil_alkohol&amp;action=edit&amp;redlink=1" class="new" title="Propargil alkohol (stran ne obstaja)">propargil alkohol</a> </td></tr> <tr> <td style="text-align:center;" colspan="3"><i><a href="/wiki/Alicikli%C4%8Dna_spojina" title="Aliciklična spojina">aliciklični</a> alkoholi</i> </td></tr> <tr> <td>C<sub>6</sub>H<sub>6</sub>(OH)<sub>6</sub> </td> <td>cikloheksan-1,2,3,4,5,6-heksol </td> <td><a href="/w/index.php?title=Inozitol&amp;action=edit&amp;redlink=1" class="new" title="Inozitol (stran ne obstaja)">inozitol</a> </td></tr> <tr> <td>C<sub>10</sub>H<sub>19</sub>OH </td> <td>2 - (2-propil)-5-metil-cikloheksan-1-ol </td> <td><a href="/w/index.php?title=Mentol&amp;action=edit&amp;redlink=1" class="new" title="Mentol (stran ne obstaja)">mentol</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Fizikalne_in_kemijske_lastnosti">Fizikalne in kemijske lastnosti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=5" title="Uredi razdelek: Fizikalne in kemijske lastnosti" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=5" title="Urejanje izvorne kode razdelka: Fizikalne in kemijske lastnosti"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hlapni alkoholi imajo značilen "pekoč" vonj oziroma okus. </p><p>Hidroksilne skupina je zaradi večje elektronegativnosti kisikovega atoma in štirih neveznih kisikovih elektronov <a href="/wiki/Polarnost" title="Polarnost">polarna</a>, zato je polarna tudi molekula alkohola. Hidroksilna skupina tvori tudi vodikove vezi, zato spadajo alkoholi med protična polarna topila. </p><p>Molekule alkoholov so pravzaprav sestavljene iz dveh povsem različnih delov: nepolarne verige ogljikovih atomov, ki je hidrofobna in polarne –OH skupine, ki je hidrofilna. V alkoholih z majhnim številom ogljikovih atomov prevladujejo polarne lastnosti, zato se metanol, etanol in propanol popolnoma mešajo z vodo. V butanolu, ki ima štiri ogljikove atome, sta oba vpliva izenačena, zato je zmerno topen v vodi (8&#160;%). Alkoholi s petimi ali več ogljikovimi atomi so zaradi prevladujočih nepolarnih lastnosti v vodi praktično netopni. Vsi nižji alkoholi se mešajo z organskimi topili. </p><p>Alkoholi imajo zaradi vodikovih vezi višja vrelišča kot primerljivi ogljikovodiki in etri: etanol ima vrelišče pri 78,29&#160;°C, heksan (sestavina bencina) 69&#160;°C, dietil eter (etoksietan) pa 34,6&#160;°C. </p> <table class="wikitable"> <tbody><tr> <th>Ime IUPAC</th> <th>Racionalna formula</th> <th>Tališče (°C)</th> <th>Vrelišče (°C)</th> <th>Topnost v vodi (g/L)</th> <th>Uporaba </th></tr> <tr> <td>metanol</td> <td>CH<sub>3</sub>OH</td> <td>−97,8</td> <td>64,7<sup id="cite_ref-Hauptmann_312_5-0" class="reference"><a href="#cite_note-Hauptmann_312-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td> <td>neomejena</td> <td>gorivo, topilo </td></tr> <tr> <td>etanol</td> <td>CH<sub>3</sub>CH<sub>2</sub>OH</td> <td>−114,1</td> <td>78,3<sup id="cite_ref-Hauptmann_312_5-1" class="reference"><a href="#cite_note-Hauptmann_312-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td> <td>neomejena</td> <td>alkoholne pijače, topilo </td></tr> <tr> <td>propan-1-ol</td> <td>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH</td> <td>−126,2</td> <td>97,2<sup id="cite_ref-Hauptmann_312_5-2" class="reference"><a href="#cite_note-Hauptmann_312-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td> <td>neomejena</td> <td>topilo </td></tr> <tr> <td>butan-1-ol</td> <td>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH</td> <td>−89,3</td> <td>117,3<sup id="cite_ref-Hauptmann_312_5-3" class="reference"><a href="#cite_note-Hauptmann_312-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td> <td>7,9</td> <td>topilo </td></tr> <tr> <td>pentan-1-ol</td> <td>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH</td> <td>−78,2</td> <td>138<sup id="cite_ref-Hauptmann_312_5-4" class="reference"><a href="#cite_note-Hauptmann_312-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td> <td>2,3</td> <td>topilo </td></tr></tbody></table> <p>Alkoholi imajo zaradi –OH skupine, podobno kot voda, kisle ali bazične lastnosti. Njihove pK<sub>a</sub> imajo vrednosti 16-19, zato so v primerjavi z vodo šibkejše kisline, z močnimi bazami, na primer z NaOH, ali z alkalijskimi kovinami, na primer z <a href="/wiki/Natrij" title="Natrij">natrijem</a> ali <a href="/wiki/Kalij" title="Kalij">kalijem</a>, pa kljub temu tvorijo soli – alkokside – s splošno formulo RO<sup>-</sup>M<sup>+</sup>: </p><p>CH<sub>3</sub>-OH + NaOH → CH<sub>3</sub>-ONa + H<sub>2</sub>O </p><p>Ker ima kisikov atom v –OH skupini štiri nevezne elektrone, imajo alkoholi tudi rahlo bazične lastnosti in reagirajo z močnimi kislinami: </p><p>CH<sub>3</sub>-OH + H<sub>2</sub>SO<sub>4</sub> → CH<sub>3</sub>-OH<sub>2</sub><sup>+</sup> + HSO<sub>4</sub><sup>-</sup> </p><p>Alkoholi lahko oksidirajo, tako da iz njih nastanejo aldehidi, ketoni ali karboksilne kisline. Iz alkoholov z odcepitvijo vode nastanejo <a href="/wiki/Alken" title="Alken">alkeni</a>. S karboksilnimi kislinami tvorijo <a href="/wiki/Ester" title="Ester">estre</a>. Zaradi štirih neveznih elektronov na kisiku v –OH skupini so alkoholi nukleofili, s predhodnim aktiviranjem pa lahko podležejo nukleofilnim substitucijam. </p> <div class="mw-heading mw-heading2"><h2 id="Uporaba">Uporaba</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=6" title="Uredi razdelek: Uporaba" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=6" title="Urejanje izvorne kode razdelka: Uporaba"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/Slika:Alcohol_by_Country.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/250px-Alcohol_by_Country.png" decoding="async" width="250" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/375px-Alcohol_by_Country.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Alcohol_by_Country.png/500px-Alcohol_by_Country.png 2x" data-file-width="1800" data-file-height="820" /></a><figcaption>Skupna vrednost porabe alkohola na prebivalca (15+), v litrih čistega alkohola<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>Alkoholi se uporabljajo v prehrambeni industriji (samo etanol), medicini (za dezinfekcijo kože, pogosto skupaj z jodom), znanosti, industriji (surovine in topila) in kot gorivo, v zadnjem času tudi za pogon <a href="/wiki/Motor" title="Motor">motorjev</a> z notranjim zgorevanjem. Etanol se zaradi majhne toksičnosti in sposobnosti raztapljanja nepolarnih snovi uporablja tudi kot topilo v medicinskih preparatih, parfumih in rastlinskih ekstraktih. </p> <div class="mw-heading mw-heading2"><h2 id="Proizvodnja">Proizvodnja</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=7" title="Uredi razdelek: Proizvodnja" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=7" title="Urejanje izvorne kode razdelka: Proizvodnja"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkoholi se na industrijski način proizvajajo na več načinov: </p> <ul><li>S <a href="/wiki/Fermentacija" title="Fermentacija">fermentacijo</a> (alkoholnim vrenjem) enostavnih sladkorjev (monosaharidov), ki so lahko naravnega izvora (<a href="/wiki/Grozdje" title="Grozdje">grozdje</a>, <a href="/wiki/Sadje" title="Sadje">sadje</a>) ali proizvedeni s hidrolizo <a href="/wiki/%C5%A0krob" title="Škrob">škroba</a> ali <a href="/wiki/Celuloza" title="Celuloza">celuloze</a> (metanol, etanol).</li> <li>Z <a href="/wiki/Adicija" title="Adicija">adicijo</a> <a href="/wiki/Voda" title="Voda">vode</a> na <a href="/wiki/Alken" title="Alken">alkene</a> pri visoki temperaturi in pritisku in prisotnosti katalizatorja (običajno <a href="/wiki/Fosforjeva_kislina" title="Fosforjeva kislina">fosforjeva kislina</a>).</li> <li>Metanol se proizvaja tudi iz <a href="/w/index.php?title=Sintezni_plin&amp;action=edit&amp;redlink=1" class="new" title="Sintezni plin (stran ne obstaja)">sinteznega plina</a> (zmes <a href="/wiki/Vodik" title="Vodik">vodika</a> in <a href="/wiki/Ogljikov_monoksid" title="Ogljikov monoksid">ogljikovega monoksida</a>) in vodika pri visoki temperaturi in pritisku in prisotnosti katalizatorja (<a href="/wiki/Baker" title="Baker">Cu</a>-ZnO-Al<sub>2</sub>O<sub>3</sub>).</li></ul> <div class="mw-heading mw-heading3"><h3 id="Endogeni_etanol">Endogeni etanol</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=8" title="Uredi razdelek: Endogeni etanol" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=8" title="Urejanje izvorne kode razdelka: Endogeni etanol"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vsi ljudje imajo v svojih organizmih vedno nekaj etanola, čeprav nikoli v življenju niso pili alkoholnih pijač. Etanol nastaja v prebavilih kot stranski produkt <a href="/wiki/Metabolizem" class="mw-redirect" title="Metabolizem">metabolizma</a> nekaterih <a href="/wiki/Bakterija" class="mw-redirect" title="Bakterija">bakterij</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Laboratorijska_sinteza">Laboratorijska sinteza</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=9" title="Uredi razdelek: Laboratorijska sinteza" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=9" title="Urejanje izvorne kode razdelka: Laboratorijska sinteza"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Za pripravo alkoholov v <a href="/wiki/Laboratorij" title="Laboratorij">laboratoriju</a> je na razpolago več metod. </p> <ul><li>Primarni alkilhalogenidi reagirajo z NaOH in KOH tako, da z nukleofilno substitucijo iz njih nastanejo primarni alkoholi. Sekundarni in terciarni halogenidi niso uporabni, ker pri njih pride do eliminacije halogenvodika in nastanka alkenov.</li> <li>Z <a href="/wiki/Redukcija" class="mw-redirect" title="Redukcija">redukcijo</a> <a href="/wiki/Aldehid" title="Aldehid">aldehidov</a> in <a href="/wiki/Keton" title="Keton">ketonov</a> z natrijevim borovim hidridom (NaBH<sub>4</sub>) ali litijevim aluminijevim hidridom (LiAlH<sub>4</sub>). Možna je tudi Meerwein-Ponndorf-Verleyeva redukcija.</li> <li>Z <a href="/wiki/Adicija" title="Adicija">adicijo</a> vode na alkene v prisotnosti kislih katalizatorjev (koncentrirana H<sub>2</sub>SO<sub>4</sub>) dobimo običajno sekundarne in terciarne alkohole. Bolj zanesljivi reakciji sta hidroboriranje in kasnejša oksidacija alkenov:</li></ul> <dl><dd>3 RCH=CH<sub>2</sub> + BH<sub>3</sub> → (RCH<sub>2</sub>-CH<sub>2</sub>)<sub>3</sub>B</dd></dl> <dl><dd>(RCH<sub>2</sub>-CH<sub>2</sub>)<sub>3</sub>B + 6 H<sub>2</sub>O<sub>2</sub> + OH<sup>-</sup> → 3 RCH<sub>2</sub>-CH<sub>2</sub>-OH + B(OH)<sub>4</sub><sup>-</sup></dd></dl> <dl><dd>in oskimerkuriranje in redukcija.</dd></dl> <ul><li><a href="/wiki/Grignardov_reagent" class="mw-redirect" title="Grignardov reagent">Grignardovi reagenti</a> reagirajo s karbonilnimi skupinami (-CHO) v sekundarne in terciarne alkohole. Sorodni reakciji sta tudi Barbierjeva in Nozaki-Hiyamova reakcija.</li> <li>Noyorijevo asimetrično hidrogeniranje je asimetrišna redukcija β-keto estrov.</li> <li><a href="/wiki/Amin" title="Amin">Amine</a> lahko z <a href="/wiki/Diazotiranje" title="Diazotiranje">diazotiranjem</a> pretvorimo v <a href="/wiki/Diazonijeva_sol" title="Diazonijeva sol">diazonijeve soli</a>, ki <a href="/wiki/Hidroliza" title="Hidroliza">hidrolizirajo</a> v alkohole.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Reakcije">Reakcije</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=10" title="Uredi razdelek: Reakcije" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=10" title="Urejanje izvorne kode razdelka: Reakcije"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Protoliza">Protoliza</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=11" title="Uredi razdelek: Protoliza" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=11" title="Urejanje izvorne kode razdelka: Protoliza"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkoholi se lahko obnašajo kot šibke <a href="/wiki/Kislina" title="Kislina">kisline</a> in odcepijo <a href="/wiki/Proton" title="Proton">proton</a>. Reakcija poteka z močnimi bazami, na primer z natrijevim hidridom (NaH), n-butillitijem (C<sub>4</sub>H<sub>9</sub>Li) ali <a href="/wiki/Kovina" title="Kovina">kovinskim</a> <a href="/wiki/Natrij" title="Natrij">natrijem</a> ali <a href="/wiki/Kalij" title="Kalij">kalijem</a>. Produkt reakcije so alkoksidi. Primer: </p><p>2 R-OH + 2 NaH → 2 R-O<sup>−</sup>Na<sup>+</sup> + 2 H<sub>2</sub> </p><p>2 R-OH + 2 Na → 2 R-O<sup>−</sup>Na<sup>+</sup> + H<sub>2</sub> </p><p>Voda ima podoben pK<sub>a</sub> kot mnogo alkoholov, zato se z NaOH vzpostavi ravnotežje, ki je običajno pomaknjeno v levo: </p><p>R-OH + NaOH ↔ R-O<sup>−</sup>Na<sup>+</sup> + H<sub>2</sub>O </p><p>Vse baze, ki se uporabljajo za deprotoniranje alkoholov so močne baze in tako kot alkoksidi zelo občutljive na vlago. </p><p>Od stabilnost alkoksidnega iona je odvisna tudi kislost alkoholov. Elektrofilne skupine, ki so vezane na ogljikov atom in vsebujejo hidroksilno skupino, deluje kot stabilizator nastalega alkoksida, kar poveča njegovo kislost, po drugi strani pa prisotnost nukleofilnih skupin povzroči nastanek manj stabilnega alkoksidnega iona. </p><p>Alkoksidi reagirajo z alkilhalogenidi in tvorijo <a href="/wiki/Eter" title="Eter">etre</a> (Williamsonova sinteza): </p><p>C<sub>2</sub>H<sub>5</sub>O<sup>−</sup>Na<sup>+</sup> + C<sub>2</sub>H<sub>5</sub>Cl → C<sub>2</sub>H<sub>5</sub>-O-C<sub>2</sub>H<sub>5</sub> + Na<sup>+</sup>Cl<sup>−</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nukleofilna_substitucija">Nukleofilna substitucija</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=12" title="Uredi razdelek: Nukleofilna substitucija" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=12" title="Urejanje izvorne kode razdelka: Nukleofilna substitucija"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>-OH skupina ni najboljša odhajajoča substituenta za nukleofilne substitucije, zato nevtralni alkoholi v takšnih reakcijah ne reagirajo. Če na kisikov atom najprej vežemo proton (H<sup>+</sup>), da dobimo vmesno spojino R-OH<sub>2</sub><sup>+</sup>, postane odhajajoča substituenta voda, ki je mnogo bolj stabilna, zato nukleofilna substitucija steče. Primer: terciarni alkoholi reagirajo s klorvodikovo kislino in tvorijo terciarne alkilhalogenide. Hidroksilna skupina se z nukleofilno substitucijo zamenja s klorom: </p><p>(CH<sub>3</sub>)<sub>3</sub>C-OH + HCl → (CH<sub>3</sub>)<sub>3</sub>C-Cl + H<sub>2</sub>O </p><p>Reakcija poteka pri sobni temperaturi. Za podobno reakcijo s primarnimi in sekundarnimi akloholi je treba alkohole predhodno aktivirati z ZnCl<sub>2</sub>. Reakcija s tionil kloridom (SO<sub>2</sub>Cl<sub>2</sub>) poteče brez predhodnega aktiviranja: </p><p>C<sub>6</sub>H<sub>5</sub>-OH + SO<sub>2</sub>Cl<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>-Cl + SO<sub>2</sub> + HCl </p><p>Alkohole lahko z bromvodikovo kislino (HBr) ali fosforjevim tribromidom (PBr<sub>3</sub>) pretvorimo v alkil bromide: </p><p>3 R-OH + PBr<sub>3</sub> → 3 R-Br + H<sub>3</sub>PO<sub>3</sub> </p><p>Z Barton-McCombijevo reakcijo s tributilin hidridom ali kompleksom trimetilboran-voda lahko iz alkoholov odcepimo kisik, tako da dobimo <a href="/wiki/Alkan" title="Alkan">alkane</a>. Reakcija je radikalska substitucija. </p> <div class="mw-heading mw-heading3"><h3 id="Eliminacija_vode_(dehidracija)"><span id="Eliminacija_vode_.28dehidracija.29"></span>Eliminacija vode (dehidracija)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=13" title="Uredi razdelek: Eliminacija vode (dehidracija)" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=13" title="Urejanje izvorne kode razdelka: Eliminacija vode (dehidracija)"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkoholi so nukleofilni, zato lahko R-OH<sub>2</sub><sup>+</sup> reagira z R-OH, tako da nastanejo etri in voda. Reakcija se v praksi izvaja bolj redko, razen za sintezo dietil etra. Bolj kot intermolekularna eliminacija vode je uporabna intramolekularna eliminacija (odcepitev vode iz ene molekule alkohola), tako da nastanejo alkeni. Reakcija poteka na splošno po <a href="/w/index.php?title=Pravilo_Zajceva&amp;action=edit&amp;redlink=1" class="new" title="Pravilo Zajceva (stran ne obstaja)">pravilu Zajceva</a>, ki pravi, da nastane najbolj stabilen (običajno najbolj substituiran) alken. Terciarni alkoholi odcepijo vodo že pri rahlo povišani temperaturi, primarni alkoholi pa zahtevajo višje temperature. </p><p>Shematski prikaz katalitske dehidracije etanola, katere produkt je eten: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Slika:DehydrationOfAlcoholWithH-.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/DehydrationOfAlcoholWithH-.svg/600px-DehydrationOfAlcoholWithH-.svg.png" decoding="async" width="600" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/DehydrationOfAlcoholWithH-.svg/900px-DehydrationOfAlcoholWithH-.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/DehydrationOfAlcoholWithH-.svg/1200px-DehydrationOfAlcoholWithH-.svg.png 2x" data-file-width="750" data-file-height="115" /></a><figcaption></figcaption></figure> <p>Bolj kontrolirana reakcija je Čugajeva eliminacija z ogljikovin disulfidom (CS<sub>2</sub>) in jodometanom (CH<sub>3</sub>I) </p> <div class="mw-heading mw-heading3"><h3 id="Estrenje">Estrenje</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=14" title="Uredi razdelek: Estrenje" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=14" title="Urejanje izvorne kode razdelka: Estrenje"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrenje je reakcija alkohola s karboksilno kislino v kateri nastane ester. Katalizator je koncentrirana žveplova kislina (H<sub>2</sub>SO<sub>4</sub>). </p><p>R-OH + R'-COOH → R'-COO-R </p><p>Da bi se reakcijsko ravnotežje pomaknilo čim bolj v desno, se pravi da bi dobili čim boljši izkoristek, iz sistema odstranjujemo vodo. Vodo odstranjujemo s prebitkom H<sub>2</sub>SO<sub>4</sub>, ki močno vežež vodo, ali tako, da uporabimo Dean-Starkov aparat. Estre lahko pripravimo tudi iz alkoholov in kislinskih kloridov v prisotnosti baz, na primer <a href="/w/index.php?title=Piridin&amp;action=edit&amp;redlink=1" class="new" title="Piridin (stran ne obstaja)">piridina</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Oksidacija">Oksidacija</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=15" title="Uredi razdelek: Oksidacija" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=15" title="Urejanje izvorne kode razdelka: Oksidacija"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Primarne alkohole (R-CH<sub>2</sub>-OH) lahko oksidiramo v aldehide (R-CHO) ali karboksilne kisline (R-COOH). Oksidacija sekundarnih alkoholov (RR'CH-OH) poteče samo do ketonov (RR'C=O). Terciarni alkoholi (RR'R"C-OH) se ne oksidirajo. </p><p>Neposredna oksidacija primarnih alkoholov do karboksilnih kisline normalno poteka preko odgovarjajočih aldehidov in aldehid hidratov: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Slika:Alcohol_to_aldehyde_to_acid_sl.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alcohol_to_aldehyde_to_acid_sl.png/400px-Alcohol_to_aldehyde_to_acid_sl.png" decoding="async" width="400" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alcohol_to_aldehyde_to_acid_sl.png/600px-Alcohol_to_aldehyde_to_acid_sl.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Alcohol_to_aldehyde_to_acid_sl.png/800px-Alcohol_to_aldehyde_to_acid_sl.png 2x" data-file-width="1510" data-file-height="230" /></a><figcaption></figcaption></figure> <p>Reakcijo pogosto prekinemo na stopnji aldehida, tako da reakcijo izvedemo v odsotnosti vode. V odsotnosti vode namreč aldehid hidrat ne more nastati in reakcija se prekine. </p><p>Oksidanti, ki se uporabljajo za oksidacijo primarnih alkoholov v aldehide, so uporabni tudi za oksidacijo sekundarnih alkoholov v ketone. Mednje spadajo: </p> <ul><li>Kromove spojine, na promer Collinsov reagent (CrO<sub>3</sub>•Py<sub>2</sub>), piridin dikromat (PDC, (C<sub>5</sub>H<sub>5</sub>NH)<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>) in piridin klorokromat (PCC, C<sub>5</sub>H<sub>5</sub>NHClCrO<sub>3</sub>).</li> <li>Aktivirani dimetil sulfoksid (DMSO, (CH<sub>3</sub>)<sub>2</sub>SO).</li> <li>Hipervalentne klorove spojine, na primer Dess-Martinov prejodinan ali 2-jodoksibenzojeva kislina.</li> <li>Katalitski tetrapropilamonijev perrutenate (TPAP ali TPAPR, N(C<sub>3</sub>H<sub>7</sub>)<sub>4</sub>RuO<sub>4</sub>).</li> <li>Katalitski 2,2,6,6-tetrametilpiperidin-1-oksil (TEMPO, (CH<sub>2</sub>)<sub>3</sub>(CMe<sub>2</sub>)<sub>2</sub>NO) v prebitku NaOCl (Anellijeva oksidacija).</li></ul> <p>Alilni in benzilni alkoholi se lahko v prisotnosti drugih alkoholov oksidirajo z nekaterimi selektivnimi oksidanti, na primer z manganovim dioksidom (MnO<sub>2</sub>). </p><p>Za oksidacijo sekundarnih alkoholov v ketone je uporaben tudi kromov trioksid (CrO<sub>3</sub>) v zmesi žveplove kisline in acetona. CrO<sub>3</sub> je v prisotnosti aluminijevega izopropoksida (Al(O-i-Pr)<sub>3</sub>) uporaben tudi za oksidacijo nekaterih ketonov, na primer cikloheksanona (C<sub>6</sub>H<sub>10</sub>O), ni pa uporaben za oksidacijo primarnih alkoholov v aldehide. </p><p>Za direktno oksidacijo primarnih alkoholov v karboksilne kisline </p><p>R-CH<sub>2</sub>-OH + [O] → R-COOH </p><p>so uporabni naslednji oksidanti: </p> <ul><li>Kalijev permanganat (KMnO<sub>4</sub>).</li> <li>Kromova kislina (raztopina CrO<sub>3</sub> v koncentrirani H<sub>2</sub>SO<sub>4</sub>).</li> <li>PDC (piridinijev dikromat, (C<sub>5</sub>H<sub>5</sub>NH)<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>) v DMF (2,5-dimetilfuran, C<sub>6</sub>H<sub>8</sub>O).</li> <li>Kisik v prisotnosti katalizatorja fino uprašene <a href="/wiki/Platina" title="Platina">platine</a> (Henysova oksidacija).</li> <li>Rutenijev tetraoksid (RuO<sub>4</sub>).</li> <li>2,2,6,6-tetrametillpiperidin-1-oksil (TEMPO, (CH<sub>2</sub>)<sub>3</sub>(CMe<sub>2</sub>)<sub>2</sub>NO).</li></ul> <p>V alkoholih, ki imajo dve hidroksilni skupini na sosednjih ogljikovih atomih, na primer 1,2-dioli, pride pri oksidaciji (na primer z natrijevim perjodatom NaIO<sub>4</sub> ali svinčevim tetraacetatom Pb(OAc)<sub>4</sub>) do prekinitve vezi med ogljikovima atomoma, tako da nastaneta dve karbonilni skupini: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Slika:Oxidative_breakage_of_1,2-diol_no_desc.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Oxidative_breakage_of_1%2C2-diol_no_desc.png/220px-Oxidative_breakage_of_1%2C2-diol_no_desc.png" decoding="async" width="220" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Oxidative_breakage_of_1%2C2-diol_no_desc.png/330px-Oxidative_breakage_of_1%2C2-diol_no_desc.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Oxidative_breakage_of_1%2C2-diol_no_desc.png/440px-Oxidative_breakage_of_1%2C2-diol_no_desc.png 2x" data-file-width="807" data-file-height="225" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Toksičnost"><span id="Toksi.C4.8Dnost"></span>Toksičnost</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=16" title="Uredi razdelek: Toksičnost" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=16" title="Urejanje izvorne kode razdelka: Toksičnost"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/Slika:Possible_long-term_effects_of_ethanol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Possible_long-term_effects_of_ethanol.svg/220px-Possible_long-term_effects_of_ethanol.svg.png" decoding="async" width="220" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Possible_long-term_effects_of_ethanol.svg/330px-Possible_long-term_effects_of_ethanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Possible_long-term_effects_of_ethanol.svg/440px-Possible_long-term_effects_of_ethanol.svg.png 2x" data-file-width="2079" data-file-height="1485" /></a><figcaption>Pregled možnih posledic dolgotrajnega uživanja etanola</figcaption></figure> <p>Etanol v alkoholnih pijačah uživajo ljudje od prazgodovine. Velika količina zaužitega alkohola povzroči opitost (intoksikacijo), po prenehanju delovanja pa več neprijetnih fizioloških učinkov, ki jim pravimo "maček": glavobol, težave z želodcem in bruhanje, občutljivost na svetlobo in hrup, otopelost, potrtost in žejo. Zelo velika količina zaužitega etanola povzroči odpoved dihalnih organov ali smrt. Zaužiti etanol zmanjšuje prištevnost, ki ima za posledico lahkomiselno ali nasilno obnašanje. </p><p>LD<sub>50</sub> etanola za podgane je 10,300&#160;mg/kg telesne mase.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Drugi alkoholi so mnogo bolj toksični, predvsem zato, ker je čas njihove razgradnje daljši, ali zato, ker med njihovo presnovo nastajajo produkti, ki so še bolj toksični od alkohola samega. Pri presnovi metanola nastaja v <a href="/wiki/Jetra" title="Jetra">jetrih</a> toksični <a href="/wiki/Formaldehid" title="Formaldehid">formaldehid</a>, ki povzroča slepoto in smrt. Učinkovit protistrup pri zastrupitvi z metanolom je etanol. Alkoholne dehidrogenaze imajo namreč mnogo večjo afiniteto do etanola kot do metanola, tako da ima ves nerazgrajeni metanol čas, da se izloči preko <a href="/wiki/Ledvice" class="mw-redirect" title="Ledvice">ledvic</a>. Že nastali formaldehid se oksidira v mravljinčno kislino in se izloči.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> </p><p>Metanol je sicer strupen, vendar je mnogo šibkejši sedativ kot etanol. Nekateri alkoholi z daljšimi verigami, na primer propanol, propan-2-ol, butanol, 2-metil-propan-2-ol (terc-butanol) imajo mnogo močnejše sedativne učinke, so pa tudi bolj toksični od etanola.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> Te alkohole imenujemo patočni alkoholi ali patočna olja in v alkoholnih pijačah niso zaželeni,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> ker slovijo po tem, da povzročajo zelo težkega "mačka", čeprav ni dokazano, da so prav oni njegovi povzročitelji.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> </p><p>Nekateri višji alkoholi se uporabljajo kot industrijska topila. Njihovo uživanje povzroča težke zdravstvene okvare<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Reference">Reference</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=17" title="Uredi razdelek: Reference" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=17" title="Urejanje izvorne kode razdelka: Reference"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><a href="/wiki/Mednarodna_zveza_za_%C4%8Disto_in_uporabno_kemijo" title="Mednarodna zveza za čisto in uporabno kemijo">IUPAC</a>, <i><a href="/w/index.php?title=IUPAC_books&amp;action=edit&amp;redlink=1" class="new" title="IUPAC books (stran ne obstaja)">Compendium of Chemical Terminology</a></i>, 2. izd. (the "Gold Book") (1997). Spletna izdaja: (2006&#8211;) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/A00204.html">Alcohols</a>". <a href="/wiki/Identifikator_digitalnega_objekta" title="Identifikator digitalnega objekta">DOI</a>: <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1351/goldbook.A00204">10.1351/goldbook.A00204</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">Lodgsdon, J.E. (1994). "Ethanol." In J.I. Kroschwitz (Ed.) Encyclopedia of Chemical Technology, 4th ed. vol. 9, p. 820. New York: John Wiley &amp; Sons.</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r5980307">.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 a,.mw-parser-output .citation .cs1-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 a,.mw-parser-output .id-lock-registration a,.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-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 a,.mw-parser-output .citation .cs1-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}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:#d33}.mw-parser-output .cs1-visible-error{color:#d33}.mw-parser-output .cs1-maint{display:none;color:#3a3;margin-left:0.3em}.mw-parser-output .cs1-format{font-size:95%}.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}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130627172123/http://www.newton.dep.anl.gov/askasci/chem03/chem03561.htm">»Metanol in slepota«</a>. Arhivirano iz <a rel="nofollow" class="external text" href="http://www.newton.dep.anl.gov/askasci/chem03/chem03561.htm">prvotnega spletišča</a> dne 27. junija 2013<span class="reference-accessdate">. Pridobljeno 24. januarja 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=neznano&amp;rft.btitle=Metanol+in+slepota&amp;rft_id=http%3A%2F%2Fwww.newton.dep.anl.gov%2Faskasci%2Fchem03%2Fchem03561.htm&amp;rfr_id=info%3Asid%2Fsl.wikipedia.org%3AAlkohol" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">William Reusch. Alcohols. VirtualText of Organic Chemistry.</span> </li> <li id="cite_note-Hauptmann_312-5"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Hauptmann_312_5-0">5,0</a></sup> <sup><a href="#cite_ref-Hauptmann_312_5-1">5,1</a></sup> <sup><a href="#cite_ref-Hauptmann_312_5-2">5,2</a></sup> <sup><a href="#cite_ref-Hauptmann_312_5-3">5,3</a></sup> <sup><a href="#cite_ref-Hauptmann_312_5-4">5,4</a></sup></span> <span class="reference-text"><a href="/w/index.php?title=Siegfried_Hauptmann&amp;action=edit&amp;redlink=1" class="new" title="Siegfried Hauptmann (stran ne obstaja)">Siegfried Hauptmann</a>: <i>Organische Chemie</i>, 2. Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1985, <a href="/wiki/Posebno:ViriKnjig/3342002808" class="internal mw-magiclink-isbn">ISBN 3-342-00280-8</a>, S.&#160;312.</span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r5980307"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.who.int/entity/substance_abuse/publications/global_status_report_2004_overview.pdf">»Global Status Report on Alcohol 2004«</a> <span class="cs1-format">(PDF)</span><span class="reference-accessdate">. Pridobljeno 28. novembra 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=neznano&amp;rft.btitle=Global+Status+Report+on+Alcohol+2004&amp;rft_id=http%3A%2F%2Fwww.who.int%2Fentity%2Fsubstance_abuse%2Fpublications%2Fglobal_status_report_2004_overview.pdf&amp;rfr_id=info%3Asid%2Fsl.wikipedia.org%3AAlkohol" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Robert S. Gable (2004). "Comparison of acute lethal toxicity of commonly abused psychoactive substances" (reprint).</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Zimmerman HE, Burkhart KK, Donovan JW. Ethylene glycol and methanol poisoning: diagnosis and treatment. Journal of Emergency Nursing. 1999 Apr;25(2):116-20. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/10097201?dopt=Abstract">PMID 10097201</a></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">Lobert S. Ethanol, isopropanol, methanol, and ethylene glycol poisoning. Critical Care Nurse. 2000 Dec;20(6):41-7. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/11878258?dopt=Abstract">PMID 11878258</a></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">McKee M, Suzcs S, Sárváry A, Adany R, Kiryanov N, Saburova L, Tomkins S, Andreev E, Leon DA. The composition of surrogate alcohols consumed in Russia. Alcoholism, Clinical and Experimental Research. 2005 Oct;29(10):1884-8. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/16269919?dopt=Abstract">PMID 16269919</a></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><a href="#cite_ref-11">↑</a></span> <span class="reference-text">Bunc M, Pezdir T, Mozina H, Mozina M, Brvar M. Butanol ingestion in an airport hangar. Human and Experimental Toxicology. 2006 Apr;25(4):195-7. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/16696295?dopt=Abstract">PMID 16696295</a></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><a href="#cite_ref-12">↑</a></span> <span class="reference-text">Woo KL. Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography. Journal of AOAC International. 2005 Sep-Oct;88(5):1419-27. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/16385992?dopt=Abstract">PMID 16385992</a></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><a href="#cite_ref-13">↑</a></span> <span class="reference-text">Lachenmeier DW, Haupt S, Schulz K. Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products. Regulatory Toxicology and Pharmacology. 2008 Apr;50(3):313-21. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/18295386?dopt=Abstract">PMID 18295386</a></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><a href="#cite_ref-14">↑</a></span> <span class="reference-text">Hori H, Fujii W, Hatanaka Y, Suwa Y. Effects of fusel oil on animal hangover models. Alcohol Clinical and Experimental Research. 2003 Aug;27(8 Suppl):37S-41S. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/12960505?dopt=Abstract">PMID 12960505</a></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><a href="#cite_ref-15">↑</a></span> <span class="reference-text">Bogomolova IN, Bukeshov MK, Bogomolov DV. The forensic medical diagnosis of intoxication of alcohol surrogates by morphological findings. (Russian) Sudebno Meditsinskaia Ekspertiza. 2004 Sep-Oct;47(5):22-5. <a class="external mw-magiclink-pmid" rel="nofollow" href="//www.ncbi.nlm.nih.gov/pubmed/15523882?dopt=Abstract">PMID 15523882</a></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Glej_tudi">Glej tudi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=18" title="Uredi razdelek: Glej tudi" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=18" title="Urejanje izvorne kode razdelka: Glej tudi"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkoholizem" title="Alkoholizem">Alkoholizem</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Zunanje_povezave">Zunanje povezave</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkohol&amp;veaction=edit&amp;section=19" title="Uredi razdelek: Zunanje povezave" class="mw-editsection-visualeditor"><span>uredi</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alkohol&amp;action=edit&amp;section=19" title="Urejanje izvorne kode razdelka: Zunanje povezave"><span>uredi kodo</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r5916282">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:#f9f9f9;display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output 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href="https://sl.wikipedia.org/w/index.php?title=Predloga:Funkcionalne_skupine&amp;action=edit"><abbr title="Uredi to predlogo" style=";;background:none transparent;color:inherit;border:none;-moz-box-shadow:none;-webkit-box-shadow:none;box-shadow:none;">u</abbr></a></li></ul></div><div id="Funkcionalne_skupine" style="font-size:114%;margin:0 4em"><a href="/wiki/Funkcionalna_skupina" title="Funkcionalna skupina">Funkcionalne skupine</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a class="mw-selflink selflink">Alkohol</a></li> <li><a href="/wiki/Aldehid" title="Aldehid">Aldehid</a></li> <li><a href="/wiki/Alkan" title="Alkan">Alkan</a></li> <li><a href="/wiki/Alken" title="Alken">Alken</a></li> <li><a href="/wiki/Alkin" title="Alkin">Alkin</a></li> <li><a href="/wiki/Amid" title="Amid">Amid</a></li> <li><a href="/wiki/Amin" title="Amin">Amin</a></li> <li><a href="/wiki/Azo_spojina" 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obstaja)">Izocianat</a></li> <li><a href="/wiki/Keton" title="Keton">Keton</a></li> <li><a href="/w/index.php?title=Nitril&amp;action=edit&amp;redlink=1" class="new" title="Nitril (stran ne obstaja)">Nitril</a></li> <li><a href="/w/index.php?title=Nitrospojina&amp;action=edit&amp;redlink=1" class="new" title="Nitrospojina (stran ne obstaja)">Nitrospojina</a></li> <li><a href="/w/index.php?title=Nitrozo&amp;action=edit&amp;redlink=1" class="new" title="Nitrozo (stran ne obstaja)">Nitrozna spojina</a></li> <li><a href="/w/index.php?title=Organski_peroksid&amp;action=edit&amp;redlink=1" class="new" title="Organski peroksid (stran ne obstaja)">Peroksid</a></li> <li><a href="/wiki/Fosforjeva_kislina" title="Fosforjeva kislina">Fosforjeva&#160;kislina</a></li> <li><a href="/w/index.php?title=Piridin&amp;action=edit&amp;redlink=1" class="new" title="Piridin (stran ne obstaja)">Piridinski&#160;derivat</a></li> <li><a href="/w/index.php?title=Sulfon&amp;action=edit&amp;redlink=1" class="new" title="Sulfon (stran ne obstaja)">Sulfon</a></li> <li><a href="/w/index.php?title=Sulfonska_kislina&amp;action=edit&amp;redlink=1" class="new" title="Sulfonska kislina (stran ne obstaja)">Sulfonska&#160;kislina</a></li> <li><a href="/w/index.php?title=Sulfoksid&amp;action=edit&amp;redlink=1" class="new" title="Sulfoksid (stran ne obstaja)">Sulfoksid</a></li> <li><a href="/w/index.php?title=Tioester&amp;action=edit&amp;redlink=1" class="new" title="Tioester (stran ne obstaja)">Tioester</a></li> <li><a href="/w/index.php?title=Tioeter&amp;action=edit&amp;redlink=1" class="new" title="Tioeter (stran ne obstaja)">Tioeter</a></li> <li><a href="/wiki/Tiol" title="Tiol">Tiol</a></li></ul> </div></td></tr></tbody></table></div> <div role="navigation" class="navbox" aria-labelledby="Normativna_kontrola_frameless&amp;#124;text-top&amp;#124;10px&amp;#124;alt=Uredite_to_na_Wikipodatkih&amp;#124;link=https&amp;#58;//www.wikidata.org/wiki/Q156#identifiers&amp;#124;class=noprint&amp;#124;Uredite_to_na_Wikipodatkih" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Normativna_kontrola_frameless&amp;#124;text-top&amp;#124;10px&amp;#124;alt=Uredite_to_na_Wikipodatkih&amp;#124;link=https&amp;#58;//www.wikidata.org/wiki/Q156#identifiers&amp;#124;class=noprint&amp;#124;Uredite_to_na_Wikipodatkih" style="font-size:114%;margin:0 4em"><a href="/wiki/Wikipedija:Normativna_kontrola" title="Wikipedija:Normativna kontrola">Normativna kontrola</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q156#identifiers" title="Uredite to na 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href="https://aleph.nkp.cz/F/?func=find-c&amp;local_base=aut&amp;ccl_term=ica=ph165165&amp;CON_LNG=ENG">Češka republika</a></span></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drugo</th><td class="navbox-list navbox-even" style="text-align:left;border-left-width:2px;border-left-style:solid;width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://catalog.archives.gov/id/10640163">National Archives (ZDA)</a></span></li></ul> </div></td></tr></tbody></table></div> <div role="navigation" class="navbox" aria-labelledby="Normativna_kontrola_frameless&amp;#124;text-top&amp;#124;10px&amp;#124;alt=Uredite_to_na_Wikipodatkih&amp;#124;link=https&amp;#58;//www.wikidata.org/wiki/Q156#identifiers&amp;#124;class=noprint&amp;#124;Uredite_to_na_Wikipodatkih" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Narodne knjižnice</th><td class="navbox-list navbox-odd" style="text-align:left;border-left-width:2px;border-left-style:solid;width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11965827j">Francija</a> <a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11965827j">(data)</a></span></li> <li><span class="uid"><a rel="nofollow" class="external text" href="http://esu.com.ua/search_articles.php?id=43812">Ukrajina</a></span></li> 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