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class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Alkanes</span> </div> </a> <ul id="toc-Alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Alkenes</span> </div> </a> <ul id="toc-Alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Alkynes</span> </div> </a> <ul id="toc-Alkynes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Functional_groups" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Functional_groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Functional groups</span> </div> </a> <button aria-controls="toc-Functional_groups-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Functional groups subsection</span> </button> <ul id="toc-Functional_groups-sublist" class="vector-toc-list"> <li id="toc-Haloalkanes_and_haloarenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Haloalkanes_and_haloarenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Haloalkanes and haloarenes</span> </div> </a> <ul id="toc-Haloalkanes_and_haloarenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alcohols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alcohols"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Alcohols</span> </div> </a> <ul id="toc-Alcohols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ethers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ethers"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Ethers</span> </div> </a> <ul id="toc-Ethers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aldehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Aldehydes</span> </div> </a> <ul id="toc-Aldehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Ketones</span> </div> </a> <ul id="toc-Ketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Carboxylic acids</span> </div> </a> <ul id="toc-Carboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carboxylates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carboxylates"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.7</span> <span>Carboxylates</span> </div> </a> <ul id="toc-Carboxylates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Esters" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esters"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.8</span> <span>Esters</span> </div> </a> <ul id="toc-Esters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acyl_groups" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acyl_groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.9</span> <span>Acyl groups</span> </div> </a> <ul id="toc-Acyl_groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acyl_halides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acyl_halides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.10</span> <span>Acyl halides</span> </div> </a> <ul id="toc-Acyl_halides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid_anhydrides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid_anhydrides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.11</span> <span>Acid anhydrides</span> </div> </a> <ul id="toc-Acid_anhydrides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.12</span> <span>Amines</span> </div> </a> <ul id="toc-Amines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Amides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.13</span> <span>Amides</span> </div> </a> <ul id="toc-Amides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nitriles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nitriles"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.14</span> <span>Nitriles</span> </div> </a> <ul id="toc-Nitriles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclic_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyclic_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.15</span> <span>Cyclic compounds</span> </div> </a> <ul id="toc-Cyclic_compounds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Order_of_precedence_of_group" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Order_of_precedence_of_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Order of precedence of group</span> </div> </a> <ul id="toc-Order_of_precedence_of_group-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Common_nomenclature_–_trivial_names" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Common_nomenclature_–_trivial_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Common nomenclature – trivial names</span> </div> </a> <button aria-controls="toc-Common_nomenclature_–_trivial_names-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Common nomenclature – trivial names subsection</span> </button> <ul id="toc-Common_nomenclature_–_trivial_names-sublist" class="vector-toc-list"> <li id="toc-Ketones_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ketones_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Ketones</span> </div> </a> <ul id="toc-Ketones_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aldehydes_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aldehydes_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Aldehydes</span> </div> </a> <ul id="toc-Aldehydes_2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Ions</span> </div> </a> <button aria-controls="toc-Ions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Ions subsection</span> </button> <ul id="toc-Ions-sublist" class="vector-toc-list"> <li id="toc-Hydron" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydron"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Hydron</span> </div> </a> <ul id="toc-Hydron-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Parent_hydride_cations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Parent_hydride_cations"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Parent hydride cations</span> </div> </a> <ul id="toc-Parent_hydride_cations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cations_and_substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cations_and_substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Cations and substitution</span> </div> </a> <ul id="toc-Cations_and_substitution-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <button aria-controls="toc-References-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle References subsection</span> </button> <ul id="toc-References-sublist" class="vector-toc-list"> <li id="toc-Bibliography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bibliography"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Bibliography</span> </div> </a> <ul id="toc-Bibliography-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">IUPAC nomenclature of organic chemistry</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox 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Available in 33 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-33" 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">33 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Organiese_nomenklatuur" title="Organiese nomenklatuur – Afrikaans" lang="af" hreflang="af" data-title="Organiese nomenklatuur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%B3%D9%85%D9%8A%D8%A9_%D9%86%D8%B8%D8%A7%D9%85%D9%8A%D8%A9_%D9%84%D9%84%D9%85%D8%B1%D9%83%D8%A8%D8%A7%D8%AA_%D8%A7%D9%84%D8%B9%D8%B6%D9%88%D9%8A%D8%A9" title="تسمية نظامية للمركبات العضوية – Arabic" lang="ar" hreflang="ar" data-title="تسمية نظامية للمركبات العضوية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Nomenclatura_quimica_d%27os_compuestos_organicos" title="Nomenclatura quimica d'os compuestos organicos – Aragonese" lang="an" hreflang="an" data-title="Nomenclatura quimica d'os compuestos organicos" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%89%E0%A6%AA%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%95_%E0%A6%AA%E0%A6%A6%E0%A7%8D%E0%A6%A7%E0%A6%A4%E0%A6%BF%E0%A6%A4%E0%A7%87_%E0%A6%9C%E0%A7%88%E0%A6%AC_%E0%A6%B0%E0%A6%B8%E0%A6%BE%E0%A6%AF%E0%A6%BC%E0%A6%A8%E0%A7%87%E0%A6%B0_%E0%A6%A8%E0%A6%BE%E0%A6%AE%E0%A6%95%E0%A6%B0%E0%A6%A3" title="ইউপ্যাক পদ্ধতিতে জৈব রসায়নের নামকরণ – Bangla" lang="bn" hreflang="bn" data-title="ইউপ্যাক পদ্ধতিতে জৈব রসায়নের নামকরণ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Nomenclatura_org%C3%A0nica" title="Nomenclatura orgànica – Catalan" lang="ca" hreflang="ca" data-title="Nomenclatura orgànica" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/N%C3%A1zvoslov%C3%AD_organick%C3%BDch_slou%C4%8Denin" title="Názvosloví organických sloučenin – Czech" lang="cs" hreflang="cs" data-title="Názvosloví organických sloučenin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Orgaaniliste_%C3%BChendite_s%C3%BCstemaatiline_nomenklatuur" title="Orgaaniliste ühendite süstemaatiline nomenklatuur – Estonian" lang="et" hreflang="et" data-title="Orgaaniliste ühendite süstemaatiline nomenklatuur" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%BD%CE%BF%CE%BC%CE%B1%CF%84%CE%BF%CE%BB%CE%BF%CE%B3%CE%AF%CE%B1_%CE%BF%CF%81%CE%B3%CE%B1%CE%BD%CE%B9%CE%BA%CF%8E%CE%BD_%CE%B5%CE%BD%CF%8E%CF%83%CE%B5%CF%89%CE%BD" title="Ονοματολογία οργανικών ενώσεων – Greek" lang="el" hreflang="el" data-title="Ονοματολογία οργανικών ενώσεων" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Nomenclatura_qu%C3%ADmica_de_los_compuestos_org%C3%A1nicos" title="Nomenclatura química de los compuestos orgánicos – Spanish" lang="es" hreflang="es" data-title="Nomenclatura química de los compuestos orgánicos" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://eu.wikipedia.org/wiki/Konposatu_organikoen_nomenklatura" title="Konposatu organikoen nomenklatura – Basque" lang="eu" hreflang="eu" data-title="Konposatu organikoen nomenklatura" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Nomenclature_des_compos%C3%A9s_organiques" title="Nomenclature des composés organiques – French" lang="fr" hreflang="fr" data-title="Nomenclature des composés organiques" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/M%C3%B3il%C3%ADn%C3%AD_org%C3%A1nacha_a_ainmni%C3%BA" title="Móilíní orgánacha a ainmniú – Irish" lang="ga" hreflang="ga" data-title="Móilíní orgánacha a ainmniú" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Nomenclatura_qu%C3%ADmica_dos_compostos_org%C3%A1nicos" title="Nomenclatura química dos compostos orgánicos – Galician" lang="gl" hreflang="gl" data-title="Nomenclatura química dos compostos orgánicos" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9C%A0%EA%B8%B0%ED%99%94%ED%95%99%EC%9D%98_IUPAC_%EB%AA%85%EB%AA%85%EB%B2%95" title="유기화학의 IUPAC 명명법 – Korean" lang="ko" hreflang="ko" data-title="유기화학의 IUPAC 명명법" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A4%A8%E0%A4%BF%E0%A4%95_%E0%A4%B0%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A5%8B%E0%A4%82_%E0%A4%95%E0%A5%80_%E0%A4%86%E0%A4%88%E0%A4%AF%E0%A5%82%E0%A4%AA%E0%A5%80%E0%A4%8F%E0%A4%B8%E0%A5%80_%E0%A4%A8%E0%A4%BE%E0%A4%AE%E0%A4%AA%E0%A4%A6%E0%A5%8D%E0%A4%A7%E0%A4%A4%E0%A4%BF" title="कार्बनिक रसायनों की आईयूपीएसी नामपद्धति – Hindi" lang="hi" hreflang="hi" data-title="कार्बनिक रसायनों की आईयूपीएसी नामपद्धति" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/IUPAC-ova_nomenklatura_organske_kemije" title="IUPAC-ova nomenklatura organske kemije – Croatian" lang="hr" hreflang="hr" data-title="IUPAC-ova nomenklatura organske kemije" data-language-autonym="Hrvatski" data-language-local-name="Croatian" 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mw-list-item"><a href="https://ro.wikipedia.org/wiki/Nomenclatura_IUPAC_a_compu%C8%99ilor_organici" title="Nomenclatura IUPAC a compușilor organici – Romanian" lang="ro" hreflang="ro" data-title="Nomenclatura IUPAC a compușilor organici" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9D%D0%BE%D0%BC%D0%B5%D0%BD%D0%BA%D0%BB%D0%B0%D1%82%D1%83%D1%80%D0%B0_%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D1%85_%D1%81%D0%BE%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D0%B9_%D0%98%D0%AE%D0%9F%D0%90%D0%9A" title="Номенклатура органических соединений ИЮПАК – Russian" lang="ru" hreflang="ru" data-title="Номенклатура органических соединений ИЮПАК" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li 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lang="sl" hreflang="sl" data-title="Nomenklatura organske kemije IUPAC" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/IUPAC_%D0%BD%D0%BE%D0%BC%D0%B5%D0%BD%D0%BA%D0%BB%D0%B0%D1%82%D1%83%D1%80%D0%B0_%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D1%81%D0%BA%D0%B8%D1%85_%D1%98%D0%B5%D0%B4%D0%B8%D1%9A%D0%B5%D1%9A%D0%B0" title="IUPAC номенклатура органских једињења – Serbian" lang="sr" hreflang="sr" data-title="IUPAC номенклатура органских једињења" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/IUPAC_nomenklatura_organskih_jedinjenja" title="IUPAC nomenklatura organskih jedinjenja – Serbo-Croatian" lang="sh" hreflang="sh" 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.ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/IUPAC_nomenclature_of_organic_chemistry" title="Special:EditPage/IUPAC nomenclature of organic chemistry">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22IUPAC+nomenclature+of+organic+chemistry%22">"IUPAC nomenclature of organic chemistry"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22IUPAC+nomenclature+of+organic+chemistry%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22IUPAC+nomenclature+of+organic+chemistry%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22IUPAC+nomenclature+of+organic+chemistry%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22IUPAC+nomenclature+of+organic+chemistry%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22IUPAC+nomenclature+of+organic+chemistry%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">April 2023</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p class="mw-empty-elt"> </p><p>In <a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a>, the <b>IUPAC nomenclature of organic chemistry</b> is a method of naming <a href="/wiki/Organic_compound" title="Organic compound">organic chemical compounds</a> as recommended<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> by the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (IUPAC). It is published in the <i><a href="/wiki/Nomenclature_of_Organic_Chemistry" title="Nomenclature of Organic Chemistry">Nomenclature of Organic Chemistry</a></i> (informally called the <a rel="nofollow" class="external text" href="https://iupac.org/what-we-do/books/bluebook/">Blue Book</a>).<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Ideally, every possible organic <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> should have a name from which an unambiguous <a href="/wiki/Structural_formula" title="Structural formula">structural formula</a> can be created. There is also an <a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">IUPAC nomenclature of inorganic chemistry</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>To avoid long and tedious names in normal communication, the official IUPAC naming recommendations are not always followed in practice, except when it is necessary to give an unambiguous and absolute definition to a compound. IUPAC names can sometimes be simpler than older names, as with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, instead of ethyl alcohol. For relatively simple molecules they can be more easily understood than non-systematic names, which must be learnt or looked over. However, the common or <a href="/wiki/Trivial_name" title="Trivial name">trivial name</a> is often substantially shorter and clearer, and so preferred. These non-systematic names are often derived from an original source of the compound. Also, very long names may be less clear than structural formulas. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Basic_principles">Basic principles</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=1" title="Edit section: Basic principles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Update plainlinks metadata ambox ambox-content ambox-Update" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/42px-Ambox_current_red_Americas.svg.png" decoding="async" width="42" height="34" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/63px-Ambox_current_red_Americas.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/84px-Ambox_current_red_Americas.svg.png 2x" data-file-width="360" data-file-height="290" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article needs to be <b>updated</b>. The reason given is: According to current nomenclature, rings are senior to chains and chain length is senior to number of multiple bonds, the list should be revisited and updated as a whole.<span class="hide-when-compact"> Please help update this article to reflect recent events or newly available information.</span> <span class="date-container"><i>(<span class="date">February 2020</span>)</i></span></div></td></tr></tbody></table> <p>In chemistry, a number of <a href="/wiki/Prefix_(linguistics)" class="mw-redirect" title="Prefix (linguistics)">prefixes</a>, <a href="/wiki/Affix" title="Affix">suffixes</a> and <a href="/wiki/Infix" title="Infix">infixes</a> are used to describe the type and position of the <a href="/wiki/Functional_group" title="Functional group">functional groups</a> in the compound. </p><p>The steps for naming an organic compound are:<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <ol><li>Identification of the most senior group. If more than one <a href="/wiki/Functional_group" title="Functional group">functional group</a>, if any, is present, the one with <a href="#Order_of_precedence_of_group">highest group precedence</a> should be used.</li> <li>Identification of the ring or chain with the maximum number of senior groups.</li> <li>Identification of the ring or chain with the most senior elements (In order: N, P, Si, B, O, S, C).</li> <li>Identification of the parent compound. Rings are senior to chains if composed of the same elements. <ol><li>For cyclic systems: Identification of the parent cyclic ring. The cyclic system must obey these rules, in order of precedence: <ol><li>It should have the most senior <a href="/wiki/Heteroatom" title="Heteroatom">heteroatom</a> (in order: N, O, S, P, Si, B).</li> <li>It should have the maximum number of rings.</li> <li>It should have the maximum number of atoms.</li> <li>It should have the maximum number of heteroatoms.</li> <li>It should have the maximum number of senior heteroatoms (in order: O, S, N, P, Si, B).</li></ol></li> <li>For chains: Identification of the parent hydrocarbon chain. This chain must obey the following rules, in order of precedence: <ol><li>It should have the maximum length.</li> <li>It should have the maximum number of heteroatoms.</li> <li>It should have the maximum number of senior heteroatoms (in order: O, S, N, P, Si, B).</li></ol></li> <li>For cyclic systems and chains after previous rules: <ol><li>It should have the maximum number of multiple, then double bonds.</li> <li>It should have the maximum number of substituents of the suffix functional group. By suffix, it is meant that the parent functional group should have a suffix, unlike halogen substituents. If more than one functional group is present, the one with highest group precedence should be used.</li></ol></li></ol></li> <li>Identification of the side-chains. Side chains are the carbon chains that are not in the parent chain, but are branched off from it.</li> <li>Identification of the remaining functional groups, if any, and naming them by their ionic prefixes (such as hydroxy for <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−OH</span>, oxy for <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=O</span>, oxyalkane for <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−R</span>, etc.).<br />Different side-chains and functional groups will be grouped together in alphabetical order. (The <a href="/wiki/IUPAC_numerical_multiplier" title="IUPAC numerical multiplier">multiplier prefixes</a> di-, tri-, etc. are not taken into consideration for grouping alphabetically. For example, ethyl comes before dihydroxy or dimethyl, as the "e" in "ethyl" precedes the "h" in "dihydroxy" and the "m" in "dimethyl" alphabetically. The "di" is not considered in either case). When both side chains and secondary functional groups are present, they should be written mixed together in one group rather than in two separate groups.</li> <li>Identification of double/triple bonds.</li> <li>Numbering of the chain. This is done by first numbering the chain in both directions (left to right and right to left), and then choosing the numbering which follows these rules, in order of precedence. Not every rule will apply to every compound, rules can be skipped if they do not apply. <ol><li>Has the lowest-numbered <a href="/wiki/Locant" title="Locant">locant</a> (or locants) for heteroatoms. Locants are the numbers on the carbons to which the substituent is directly attached.</li> <li>Has the lowest-numbered locants for the indicated hydrogen. The indicated hydrogen is for some unsaturated heterocyclic compounds. It refers to the hydrogen atoms not attached to atoms with double bonds in the ring system.</li> <li>Has the lowest-numbered locants for the suffix functional group.</li> <li>Has the lowest-numbered locants for multiple bonds ('ene', 'yne'), and hydro prefixes. (The locant of a multiple bond is the number of the adjacent carbon with a lower number).</li> <li>Has the lowest-numbered locants for all substituents cited by prefixes.</li> <li>Has the lowest-numbered locants for substituents in order of citation (for example: in a cyclic ring with only bromine and chlorine functional groups, alphabetically bromo- is cited before chloro- and would receive the lower locant).</li></ol></li> <li>Numbering of the various substituents and bonds with their locants. If there is more than one of the same type of substituent/double bond, a prefix is added showing how many there are (di – 2, tri – 3, tetra – 4, then as for the number of carbons below with 'a' added at the end)</li></ol> <p>The numbers for that type of side chain will be grouped in ascending order and written before the name of the side-chain. If there are two side-chains with the same <a href="/wiki/Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha carbon</a>, the number will be written twice. Example: 2,2,3-trimethyl- . If there are both double bonds and triple bonds, "en" (double bond) is written before "yne" (triple bond). When the main functional group is a terminal functional group (a group which can exist only at the end of a chain, like formyl and carboxyl groups), there is no need to number it. </p> <ol><li>Arrangement in this form: Group of side chains and secondary functional groups with numbers made in step 6 + prefix of parent hydrocarbon chain (eth, meth) + double/triple bonds with numbers (or "ane") + primary functional group suffix with numbers.<br />Wherever it says "with numbers", it is understood that between the word and the numbers, the prefix (di-, tri-) is used.</li> <li>Adding of punctuation: <ol><li>Commas are put between numbers (2 5 5 becomes 2,5,5)</li> <li>Hyphens are put between a number and a letter (2 5 5 trimethylheptane becomes 2,5,5-trimethylheptane)</li> <li>Successive words are merged into one word (trimethyl heptane becomes trimethylheptane)<br /> Note: IUPAC uses one-word names throughout. This is why all parts are connected.</li></ol></li></ol> <p>The resulting name appears as: </p> <dl><dd>#,#-di<side chain>-#-<secondary functional group>-#-<side chain>-#,#,#-tri<secondary functional group><parent chain prefix><If all bonds are single bonds, use "ane">-#,#-di<double bonds>-#-<triple bonds>-#-<primary functional group></dd></dl> <p>where each "#" represents a number. The group secondary functional groups and side chains may not look the same as shown here, as the side chains and secondary functional groups are arranged alphabetically. The di- and tri- have been used just to show their usage. (di- after #,#, tri- after #,#,#, etc.) </p> <div class="mw-heading mw-heading3"><h3 id="Example">Example</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=2" title="Edit section: Example"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Here is a sample molecule with the parent carbons numbered: </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC_naming_example_with_carbons.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/6/69/IUPAC_naming_example_with_carbons.png" decoding="async" width="523" height="184" class="mw-file-element" data-file-width="523" data-file-height="184" /></a><figcaption></figcaption></figure> <p>For simplicity, here is an image of the same molecule, where the hydrogens in the parent chain are removed and the carbons are shown by their numbers: </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC_naming_example_without_carbons.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/5/5b/IUPAC_naming_example_without_carbons.png" decoding="async" width="523" height="184" class="mw-file-element" data-file-width="523" data-file-height="184" /></a><figcaption></figcaption></figure> <p>Now, following the above steps: </p> <ol><li>The parent <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> chain has 23 carbons. It is called tricosa-.</li> <li>The functional groups with the highest precedence are the two ketone groups. <ol><li>The groups are on carbon atoms 3 and 9. As there are two, we write 3,9-dione.</li> <li>The numbering of the molecule is based on the ketone groups. When numbering from left to right, the ketone groups are numbered 3 and 9. When numbering from right to left, the ketone groups are numbered 15 and 21. 3 is less than 15, therefore the ketones are numbered 3 and 9. The smaller number is always used, not the sum of the constituents numbers.</li></ol></li> <li>The side chains are: an ethyl- at carbon 4, an ethyl- at carbon 8, and a butyl- at carbon 12. <br />Note: the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−O−CH<sub class="template-chem2-sub">3</sub></span> at carbon atom 15 is not a side chain, but it is a methoxy functional group. <ul><li>There are two ethyl- groups. They are combined to create, 4,8-diethyl.</li> <li>The side chains are grouped like this: 12-butyl-4,8-diethyl. (But this is not necessarily the final grouping, as functional groups may be added in between to ensure all groups are listed alphabetically.)</li></ul></li> <li>The secondary functional groups are: a hydroxy- at carbon 5, a chloro- at carbon 11, a methoxy- at carbon 15, and a bromo- at carbon 18. Grouped with the side chains, this gives 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxy.</li> <li>There are two double bonds: one between carbons 6 and 7, and one between carbons 13 and 14. They would be called "6,13-diene", but the presence of alkynes switches it to 6,13-dien. There is one triple bond between carbon atoms 19 and 20. It will be called 19-yne.</li> <li>The arrangement (with punctuation) is: 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricosa-6,13-dien-19-yne-3,9-dione</li> <li>Finally, due to <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis-trans isomerism</a>, we have to specify the relative orientation of functional groups around each double bond. For this example, both double bonds are trans isomers, so we have (6<i>E</i>,13<i>E</i>)</li></ol> <p>The final name is (6<i>E</i>,13<i>E</i>)-18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricosa-6,13-dien-19-yne-3,9-dione. </p> <div class="mw-heading mw-heading2"><h2 id="Hydrocarbons">Hydrocarbons</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=3" title="Edit section: Hydrocarbons"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkanes">Alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=4" title="Edit section: Alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkane" title="Alkane">Alkane</a></div> <p><a href="/wiki/Straight-chain" class="mw-redirect" title="Straight-chain">Straight-chain</a> alkanes take the suffix "<a href="/wiki/-ane" title="-ane">-ane</a>" and are prefixed depending on the number of carbon atoms in the chain, following standard rules. The first few are: </p> <table class="wikitable" style="text-align: center;"> <tbody><tr> <th>Number of carbons </th> <td>1</td> <td>2</td> <td>3</td> <td>4</td> <td>5</td> <td>6</td> <td>7</td> <td>8</td> <td>9</td> <td>10</td> <td>11</td> <td>12</td> <td>13</td> <td>14</td> <td>15</td> <td>16</td> <td>17</td> <td>18</td> <td>19</td> <td>20 </td></tr> <tr> <th>Prefix </th> <td>Meth</td> <td>Eth</td> <td>Prop</td> <td>But</td> <td>Pent</td> <td>Hex</td> <td>Hept</td> <td>Oct</td> <td>Non</td> <td>Dec</td> <td>Undec</td> <td>Dodec</td> <td>Tridec</td> <td>Tetradec</td> <td>Pentadec</td> <td>Hexadec</td> <td>Heptadec</td> <td>Octadec</td> <td>Nonadec</td> <td>Icos </td></tr> </tbody></table> <p>For example, the simplest alkane is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub></span> methane, and the nine-carbon alkane <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">7</sub>CH<sub class="template-chem2-sub">3</sub></span> is named <a href="/wiki/Nonane" title="Nonane">nonane</a>. The names of the first four alkanes were <a href="/wiki/Back-formation" title="Back-formation">derived</a> from <a href="/wiki/Methanol" title="Methanol">methanol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> and <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>, respectively. The rest are named with a <a href="/wiki/Greek_language" title="Greek language">Greek</a> numeric prefix, with the exceptions of nonane which has a <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> prefix, and <a href="/wiki/Undecane" title="Undecane">undecane</a> which has mixed-language prefixes. </p><p><a href="/wiki/Cycloalkane" title="Cycloalkane">Cyclic alkanes</a> are simply prefixed with "cyclo-": for example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">8</sub></span> is cyclobutane (not to be confused with <a href="/wiki/Butene" title="Butene">butene</a>) and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub></span> is <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> (not to be confused with <a href="/wiki/Hexene" title="Hexene">hexene</a>). </p> <div align="center"><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:IUPAC-alkane-1.svg" class="mw-file-description" title="IUPAC-alkane-1.svg"><img alt="IUPAC-alkane-1.svg" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkane-1.svg/136px-IUPAC-alkane-1.svg.png" decoding="async" width="136" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkane-1.svg/204px-IUPAC-alkane-1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkane-1.svg/272px-IUPAC-alkane-1.svg.png 2x" data-file-width="136" data-file-height="148" /></a></span> <span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:IUPAC-alkane-2.svg" class="mw-file-description" title="IUPAC-alkane-2.svg"><img alt="IUPAC-alkane-2.svg" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/IUPAC-alkane-2.svg/258px-IUPAC-alkane-2.svg.png" decoding="async" width="258" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/IUPAC-alkane-2.svg/387px-IUPAC-alkane-2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/IUPAC-alkane-2.svg/516px-IUPAC-alkane-2.svg.png 2x" data-file-width="258" data-file-height="135" /></a></span></div> <p>Branched alkanes are named as a straight-chain alkane with attached <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> groups. They are prefixed with a number indicating the carbon the group is attached to, counting from the end of the alkane chain. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CHCH<sub class="template-chem2-sub">3</sub></span>, commonly known as <a href="/wiki/Isobutane" title="Isobutane">isobutane</a>, is treated as a propane chain with a methyl group bonded to the middle (2) carbon, and given the systematic name 2-methylpropane. However, although the name 2-methylpropane <i>could</i> be used, it is easier and more logical to call it simply methylpropane – the methyl group could not possibly occur on any of the other carbon atoms (that would lengthen the chain and result in butane, not propane) and therefore the use of the number "2" is unnecessary. </p><p>If there is ambiguity in the position of the substituent, depending on which end of the alkane chain is counted as "1", then numbering is chosen so that the smaller number is used. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CHCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> (isopentane) is named 2-methylbutane, not 3-methylbutane. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-alkane-3.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/IUPAC-alkane-3.svg/146px-IUPAC-alkane-3.svg.png" decoding="async" width="146" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/IUPAC-alkane-3.svg/219px-IUPAC-alkane-3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/IUPAC-alkane-3.svg/292px-IUPAC-alkane-3.svg.png 2x" data-file-width="146" data-file-height="127" /></a><figcaption></figcaption></figure> <p>If there are multiple side-branches of the same size alkyl group, their positions are separated by commas and the group prefixed with multiplier prefixes depending on the number of branches. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span> (neopentane) is named 2,2-dimethylpropane. If there are different groups, they are added in alphabetical order, separated by commas or hyphens. The longest possible main alkane chain is used; therefore 3-ethyl-4-methylhexane instead of 2,3-diethylpentane, even though these describe equivalent structures. The di-, tri- etc. prefixes are ignored for the purpose of alphabetical ordering of <a href="/wiki/Side_chain" title="Side chain">side chains</a> (e.g. 3-ethyl-2,4-dimethylpentane, not 2,4-dimethyl-3-ethylpentane). </p> <div align="center"><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:IUPAC-alkane-4.svg" class="mw-file-description" title="IUPAC-alkane-4.svg"><img alt="IUPAC-alkane-4.svg" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/IUPAC-alkane-4.svg/349px-IUPAC-alkane-4.svg.png" decoding="async" width="349" height="161" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/IUPAC-alkane-4.svg/524px-IUPAC-alkane-4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/IUPAC-alkane-4.svg/698px-IUPAC-alkane-4.svg.png 2x" data-file-width="349" data-file-height="161" /></a></span> <span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:IUPAC-alkane-5.svg" class="mw-file-description" title="IUPAC-alkane-5.svg"><img alt="IUPAC-alkane-5.svg" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/IUPAC-alkane-5.svg/230px-IUPAC-alkane-5.svg.png" decoding="async" width="230" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/IUPAC-alkane-5.svg/345px-IUPAC-alkane-5.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/IUPAC-alkane-5.svg/460px-IUPAC-alkane-5.svg.png 2x" data-file-width="230" data-file-height="131" /></a></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkenes">Alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=5" title="Edit section: Alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkene" title="Alkene">Alkene</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-alkene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkene.svg/269px-IUPAC-alkene.svg.png" decoding="async" width="269" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkene.svg/404px-IUPAC-alkene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/IUPAC-alkene.svg/538px-IUPAC-alkene.svg.png 2x" data-file-width="269" data-file-height="170" /></a><figcaption></figcaption></figure> <p>Alkenes are named for their parent alkane chain with the suffix "<a href="/wiki/-ene" title="-ene">-ene</a>" and a numerical root indicating the position of the carbon with the lower number for each double bond in the chain: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is but-1-ene. Multiple double bonds take the form -diene, -triene, etc., with the size prefix of the chain taking an extra "a": <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCH=CH<sub class="template-chem2-sub">2</sub></span> is buta-1,3-diene. Simple <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">cis and trans</a> <a href="/wiki/Geometric_isomerism" class="mw-redirect" title="Geometric isomerism">isomers</a> may be indicated with a prefixed <i>cis-</i> or <i>trans-</i>: <i>cis</i>-but-2-ene, <i>trans</i>-but-2-ene. However, <i>cis-</i> and <i>trans-</i> are <i>relative</i> descriptors. It is IUPAC convention to describe all alkenes using <i>absolute</i> descriptors of <i>Z-</i> (same side) and <i>E-</i> (opposite) with the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">Cahn–Ingold–Prelog priority rules</a> (see also <a href="/wiki/E%E2%80%93Z_notation" title="E–Z notation">E–Z notation</a>). </p> <div class="mw-heading mw-heading3"><h3 id="Alkynes">Alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=6" title="Edit section: Alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-alkyne.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/IUPAC-alkyne.svg/218px-IUPAC-alkyne.svg.png" decoding="async" width="218" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/IUPAC-alkyne.svg/327px-IUPAC-alkyne.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/IUPAC-alkyne.svg/436px-IUPAC-alkyne.svg.png 2x" data-file-width="218" data-file-height="85" /></a><figcaption></figcaption></figure><p> Alkynes are named using the same system, with the suffix "<a href="/wiki/-yne" title="-yne">-yne</a>" indicating a triple bond: ethyne (<a href="/wiki/Acetylene" title="Acetylene">acetylene</a>), propyne (<a href="/wiki/Methylacetylene" class="mw-redirect" title="Methylacetylene">methylacetylene</a>). </p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Functional_groups">Functional groups</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=7" title="Edit section: Functional groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Functional_group#Table_of_common_functional_groups" title="Functional group">Functional group § Table of common functional groups</a></div> <div class="mw-heading mw-heading3"><h3 id="Haloalkanes_and_haloarenes">Haloalkanes and haloarenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=8" title="Edit section: Haloalkanes and haloarenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> and <a href="/wiki/Haloarene" class="mw-redirect" title="Haloarene">Haloarene</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-haloalkane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/IUPAC-haloalkane.svg/393px-IUPAC-haloalkane.svg.png" decoding="async" width="393" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/IUPAC-haloalkane.svg/590px-IUPAC-haloalkane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/IUPAC-haloalkane.svg/786px-IUPAC-haloalkane.svg.png 2x" data-file-width="393" data-file-height="134" /></a><figcaption></figcaption></figure><p> In haloalkanes and haloarenes (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−X</span>), <a href="/wiki/Halogen" title="Halogen">Halogen</a> functional groups are prefixed with the bonding position and take the form of fluoro-, chloro-, bromo-, iodo-, etc., depending on the halogen. Multiple groups are dichloro-, trichloro-, etc., and dissimilar groups are ordered alphabetically as before. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHCl<sub class="template-chem2-sub">3</sub></span> (<a href="/wiki/Chloroform" title="Chloroform">chloroform</a>) is trichloromethane. The anesthetic <a href="/wiki/Halothane" title="Halothane">halothane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>CHBrCl</span>) is 2-bromo-2-chloro-1,1,1-trifluoroethane.</p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Alcohols">Alcohols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=9" title="Edit section: Alcohols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">Alcohols</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-alcohol-1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/IUPAC-alcohol-1.svg/369px-IUPAC-alcohol-1.svg.png" decoding="async" width="369" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/IUPAC-alcohol-1.svg/554px-IUPAC-alcohol-1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3b/IUPAC-alcohol-1.svg/738px-IUPAC-alcohol-1.svg.png 2x" data-file-width="369" data-file-height="101" /></a><figcaption></figcaption></figure> <p>Alcohols (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−OH</span>) take the suffix "<a href="/wiki/-ol" title="-ol">-ol</a>" with a numerical suffix indicating the bonding position: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH</span> is propan-1-ol. The suffixes <span class="nowrap">-diol</span>, <span class="nowrap">-triol</span>, <span class="nowrap">-tetrol</span>, etc., are used for multiple <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span> groups: <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>OHCH<sub class="template-chem2-sub">2</sub>OH</span> is ethane-1,2-diol. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-alcohol-2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/IUPAC-alcohol-2.svg/174px-IUPAC-alcohol-2.svg.png" decoding="async" width="174" height="124" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/IUPAC-alcohol-2.svg/261px-IUPAC-alcohol-2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/IUPAC-alcohol-2.svg/348px-IUPAC-alcohol-2.svg.png 2x" data-file-width="174" data-file-height="124" /></a><figcaption></figcaption></figure><p> If higher precedence functional groups are present (see <i><a class="mw-selflink-fragment" href="#Order_of_precedence_of_group">order of precedence</a></i>, below), the prefix "hydroxy" is used with the bonding position: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CHOHCOOH</span> is 2-hydroxypropanoic acid. </p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Ethers">Ethers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=10" title="Edit section: Ethers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Ethers" class="mw-redirect" title="Ethers">Ethers</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-ether.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/IUPAC-ether.svg/405px-IUPAC-ether.svg.png" decoding="async" width="405" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/IUPAC-ether.svg/608px-IUPAC-ether.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/IUPAC-ether.svg/810px-IUPAC-ether.svg.png 2x" data-file-width="405" data-file-height="116" /></a><figcaption></figcaption></figure> <p>Ethers (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−O−R</span>) consist of an oxygen atom between the two attached carbon chains. The shorter of the two chains becomes the first part of the name with the -ane suffix changed to -oxy, and the longer alkane chain becomes the suffix of the name of the ether. Thus, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OCH<sub class="template-chem2-sub">3</sub></span> is methoxymethane, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is <a href="/wiki/Methoxyethane" title="Methoxyethane">methoxyethane</a> (<i>not</i> ethoxymethane). If the oxygen is not attached to the end of the main alkane chain, then the whole shorter alkyl-plus-ether group is treated as a side-chain and prefixed with its bonding position on the main chain. Thus <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OCH(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> is 2-methoxypropane. </p><p>Alternatively, an ether chain can be named as an alkane in which one carbon is replaced by an oxygen, a replacement denoted by the prefix "oxa". For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> could also be called 2-oxabutane, and an <a href="/wiki/Epoxide" title="Epoxide">epoxide</a> could be called oxacyclopropane. This method is especially useful when both groups attached to the oxygen atom are complex.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Aldehydes">Aldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=11" title="Edit section: Aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">Aldehydes</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-aldehyde.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/IUPAC-aldehyde.svg/244px-IUPAC-aldehyde.svg.png" decoding="async" width="244" height="218" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/IUPAC-aldehyde.svg/366px-IUPAC-aldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/IUPAC-aldehyde.svg/488px-IUPAC-aldehyde.svg.png 2x" data-file-width="244" data-file-height="218" /></a><figcaption></figcaption></figure> <p>Aldehydes (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH=O</span>) take the suffix "<a href="/wiki/-al" title="-al">-al</a>". If other functional groups are present, the chain is numbered such that the aldehyde carbon is in the "1" position, unless functional groups of higher precedence are present. </p><p> If a prefix form is required, "oxo-" is used (as for ketones), with the position number indicating the end of a chain: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHOCH<sub class="template-chem2-sub">2</sub>COOH</span> is 3-oxopropanoic acid. If the carbon in the carbonyl group cannot be included in the attached chain (for instance in the case of <a href="/wiki/Cyclic_aldehyde" class="mw-redirect" title="Cyclic aldehyde">cyclic aldehydes</a>), the prefix "formyl-" or the suffix "-carbaldehyde" is used: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">11</sub>CHO</span> is cyclohexanecarbaldehyde. If an aldehyde is attached to a benzene and is the main functional group, the suffix becomes benzaldehyde.</p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Ketones">Ketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=12" title="Edit section: Ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">Ketones</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-ketone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/IUPAC-ketone.svg/315px-IUPAC-ketone.svg.png" decoding="async" width="315" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/IUPAC-ketone.svg/473px-IUPAC-ketone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/IUPAC-ketone.svg/630px-IUPAC-ketone.svg.png 2x" data-file-width="315" data-file-height="121" /></a><figcaption></figcaption></figure><p> In general ketones (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C=O</span>) take the suffix "<a href="/wiki/-one" title="-one">-one</a>" (pronounced <i>own</i>, not <i>won</i>) with a suffixed position number: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>COCH<sub class="template-chem2-sub">3</sub></span> is pentan-2-one. If a higher precedence suffix is in use, the prefix "oxo-" is used: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>COCH<sub class="template-chem2-sub">2</sub>CHO</span> is 3-oxohexanal. </p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Carboxylic_acids">Carboxylic acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=13" title="Edit section: Carboxylic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">Carboxylic acids</a></div> <figure class="mw-halign-right" typeof="mw:File"><a href="/wiki/File:IUPAC-carboxylic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/IUPAC-carboxylic_acid.svg/150px-IUPAC-carboxylic_acid.svg.png" decoding="async" width="150" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/IUPAC-carboxylic_acid.svg/225px-IUPAC-carboxylic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/IUPAC-carboxylic_acid.svg/300px-IUPAC-carboxylic_acid.svg.png 2x" data-file-width="106" data-file-height="109" /></a><figcaption></figcaption></figure> <p>In general, carboxylic acids (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)OH</span>) are named with the suffix <i><a href="/wiki/-oic_acid" class="mw-redirect" title="-oic acid">-oic acid</a></i> (etymologically a <a href="/wiki/Back-formation" title="Back-formation">back-formation</a> from <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a>). As with aldehydes, the <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a> functional group must take the "1" position on the main chain and so the locant need not be stated. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−CH(OH)−COOH</span> (<a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a>) is named 2-hydroxypropanoic acid with no "1" stated. Some traditional names for common carboxylic acids (such as <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>) are in such widespread use that they are <a href="/wiki/Preferred_IUPAC_name#Retained_IUPAC_names" title="Preferred IUPAC name">retained</a> in IUPAC nomenclature,<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> though systematic names like ethanoic acid are also used. Carboxylic acids attached to a benzene ring are <a href="/wiki/Structural_analog" title="Structural analog">structural analogs</a> of benzoic acid (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">Ph</a>−COOH</span>) and are named as one of its derivatives. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Zitronens%C3%A4ure_-_Citric_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/200px-Zitronens%C3%A4ure_-_Citric_acid.svg.png" decoding="async" width="200" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/300px-Zitronens%C3%A4ure_-_Citric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/400px-Zitronens%C3%A4ure_-_Citric_acid.svg.png 2x" data-file-width="256" data-file-height="116" /></a><figcaption>Citric acid</figcaption></figure> <p>If there are multiple carboxyl groups on the same parent chain, multiplying prefixes are used: <a href="/wiki/Malonic_acid" title="Malonic acid">Malonic acid</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>(COOH)<sub class="template-chem2-sub">2</sub></span>, is systematically named propanedioic acid. Alternatively, the suffix <span class="nowrap">"-carboxylic acid"</span> can be used in place of "oic acid", combined with a multiplying prefix if necessary – <a href="/wiki/Mellitic_acid" title="Mellitic acid">mellitic acid</a> is benzenehexacarboxylic acid, for example. In the latter case, the carbon atoms in the carboxyl groups do <i>not</i> count as being part of the main chain, a rule that also applies to the prefix form "carboxy-". <a href="/wiki/Citric_acid" title="Citric acid">Citric acid</a> serves as an example: it is formally named <span class="nowrap">2-hydroxypropane-1,2,3-tricarboxylic acid</span> rather than <span class="nowrap">3-carboxy-3-hydroxypentanedioic acid</span>. </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Carboxylates">Carboxylates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=14" title="Edit section: Carboxylates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Carboxylate" title="Carboxylate">Carboxylate</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Carboksyl_ominus.svg" class="mw-file-description" title="formula of a carboxylate ion"><img alt="formula of a carboxylate ion" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Carboksyl_ominus.svg/169px-Carboksyl_ominus.svg.png" decoding="async" width="169" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Carboksyl_ominus.svg/254px-Carboksyl_ominus.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Carboksyl_ominus.svg/338px-Carboksyl_ominus.svg.png 2x" data-file-width="169" data-file-height="175" /></a><figcaption>formula of a carboxylate ion</figcaption></figure> <p><a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">Salts</a> of carboxylic acids are named following the usual <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a>-then-<a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> conventions used for <a href="/wiki/Ionic_compounds" class="mw-redirect" title="Ionic compounds">ionic compounds</a> in both IUPAC and common nomenclature systems. The name of the carboxylate anion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)O<sup class="template-chem2-sup">−</sup></span>) is derived from that of the parent acid by replacing the "–oic acid" ending with "–oate" or "carboxylate." For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaC<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CO<sub class="template-chem2-sub">2</sub></span>, the sodium salt of <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>COOH</span>), is called sodium benzoate. Where an acid has both a systematic and a common name (like <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH</span>, for example, which is known as both <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> and as ethanoic acid), its salts can be named from either parent name. Thus, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KCH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub></span> can be named as <a href="/wiki/Potassium_acetate" title="Potassium acetate">potassium acetate</a> or as potassium ethanoate. The prefix form, is "carboxylato-". </p> <div class="mw-heading mw-heading3"><h3 id="Esters">Esters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=15" title="Edit section: Esters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Esters" class="mw-redirect" title="Esters">Esters</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-ester-1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/IUPAC-ester-1.svg/405px-IUPAC-ester-1.svg.png" decoding="async" width="405" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/IUPAC-ester-1.svg/608px-IUPAC-ester-1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/IUPAC-ester-1.svg/810px-IUPAC-ester-1.svg.png 2x" data-file-width="405" data-file-height="116" /></a><figcaption></figcaption></figure> <p>Esters (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)O−R'</span>) are named as alkyl derivatives of carboxylic acids. The alkyl (R') group is named first. The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)O</span> part is then named as a separate word based on the carboxylic acid name, with the ending changed from "-oic acid" to "<a href="/wiki/-oate" title="-oate">-oate</a>" or "-carboxylate" For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>COOCH<sub class="template-chem2-sub">3</sub></span> is methyl pentanoate, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CHCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>COOCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is ethyl 4-methylpentanoate. For esters such as <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span>), <a href="/wiki/Ethyl_formate" title="Ethyl formate">ethyl formate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCOOCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span>) or dimethyl phthalate that are based on common acids, IUPAC recommends use of these established names, called <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_511.htm">retained names</a>. The "-oate" changes to "-ate." Some simple examples, named both ways, are shown in the figure above. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-ester-2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/IUPAC-ester-2.svg/199px-IUPAC-ester-2.svg.png" decoding="async" width="199" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/IUPAC-ester-2.svg/299px-IUPAC-ester-2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/IUPAC-ester-2.svg/398px-IUPAC-ester-2.svg.png 2x" data-file-width="199" data-file-height="103" /></a><figcaption></figcaption></figure><p> If the alkyl group is not attached at the end of the chain, the bond position to the ester group is suffixed before "-yl": <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH(CH<sub class="template-chem2-sub">3</sub>)OOCCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> may be called butan-2-yl propanoate or butan-2-yl propionate.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2012)">citation needed</span></a></i>]</sup>. The prefix form is "oxycarbonyl-" with the (R') group preceding. </p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Acyl_groups">Acyl groups</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=16" title="Edit section: Acyl groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acyl_group" title="Acyl group">Acyl group</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acyl_group_V.0.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Acyl_group_V.0.svg/400px-Acyl_group_V.0.svg.png" decoding="async" width="400" height="221" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Acyl_group_V.0.svg/600px-Acyl_group_V.0.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Acyl_group_V.0.svg/800px-Acyl_group_V.0.svg.png 2x" data-file-width="456" data-file-height="252" /></a><figcaption></figcaption></figure> <p>Acyl groups are named by stripping the "-ic acid" of the corresponding carboxylic acid and replacing it with "-yl." For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO−R</span> is called ethanoyl-R. </p> <div class="mw-heading mw-heading3"><h3 id="Acyl_halides">Acyl halides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=17" title="Edit section: Acyl halides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acyl-halide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/400px-Acyl-halide.svg.png" decoding="async" width="400" height="372" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/600px-Acyl-halide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/800px-Acyl-halide.svg.png 2x" data-file-width="512" data-file-height="476" /></a><figcaption></figcaption></figure> <p>Simply add the name of the attached halide to the end of the acyl group. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COCl</span> is ethanoyl chloride. An alternate suffix is "-carbonyl halide" as opposed to "-oyl halide". The prefix form is "halocarbonyl-". </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acetyl_chloride.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/400px-Acetyl_chloride.svg.png" decoding="async" width="400" height="313" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/600px-Acetyl_chloride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/800px-Acetyl_chloride.svg.png 2x" data-file-width="453" data-file-height="354" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Acid_anhydrides">Acid anhydrides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=18" title="Edit section: Acid anhydrides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">Organic acid anhydride</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg/220px-FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg.png" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg/330px-FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg/440px-FunktionelleGruppen_Carbons%C3%A4ureanhydrid.svg.png 2x" data-file-width="213" data-file-height="116" /></a><figcaption></figcaption></figure> <p>Acid anhydrides (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−O−C(=O)−R</span>) have two acyl groups linked by an oxygen atom. If both acyl groups are the same, then the name of the carboxylic acid with the word acid is replaced with the word <i>anhydride</i> and the IUPAC name consists of two words. If the acyl groups are different, then they are named in alphabetical order in the same way, with <i>anhydride</i> replacing <i>acid</i> and IUPAC name consists of three words. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO−O−OCCH<sub class="template-chem2-sub">3</sub></span> is called <i>ethanoic anhydride</i> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO−O−OCCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is called <i>ethanoic propanoic anhydride</i>. </p> <div class="mw-heading mw-heading3"><h3 id="Amines">Amines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=19" title="Edit section: Amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Amine" title="Amine">Amine</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-amine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/IUPAC-amine.svg/364px-IUPAC-amine.svg.png" decoding="async" width="364" height="224" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/IUPAC-amine.svg/546px-IUPAC-amine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/IUPAC-amine.svg/728px-IUPAC-amine.svg.png 2x" data-file-width="364" data-file-height="224" /></a><figcaption></figcaption></figure> <p>Amines (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−NH<sub class="template-chem2-sub">2</sub></span>) are named for the attached alkane chain with the suffix "-amine" (e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>NH<sub class="template-chem2-sub">2</sub></span> methanamine). If necessary, the bonding position is suffixed: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>NH<sub class="template-chem2-sub">2</sub></span> propan-1-amine, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CHNH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> propan-2-amine. The prefix form is "amino-". </p><p>For secondary amines (of the form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−NH−R</span>), the longest carbon chain attached to the nitrogen atom becomes the primary name of the amine; the other chain is prefixed as an alkyl group with location prefix given as an italic <i>N</i>: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>NHCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is <i>N</i>-methylethanamine. Tertiary amines (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−NR−R</span>) are treated similarly: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>N(CH<sub class="template-chem2-sub">3</sub>)CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span> is <i>N</i>-ethyl-<i>N</i>-methylpropanamine. Again, the substituent groups are ordered alphabetically. </p> <div class="mw-heading mw-heading3"><h3 id="Amides">Amides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=20" title="Edit section: Amides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Amide" title="Amide">Amide</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-amide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/IUPAC-amide.svg/286px-IUPAC-amide.svg.png" decoding="async" width="286" height="124" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/IUPAC-amide.svg/429px-IUPAC-amide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/IUPAC-amide.svg/572px-IUPAC-amide.svg.png 2x" data-file-width="286" data-file-height="124" /></a><figcaption></figcaption></figure> <p>Amides (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)NH<sub class="template-chem2-sub">2</sub></span>) take the suffix "-amide", or "-carboxamide" if the carbon in the amide group cannot be included in the main chain. The prefix form is "carbamoyl-". e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCONH<sub class="template-chem2-sub">2</sub></span> methanamide, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CONH<sub class="template-chem2-sub">2</sub></span> ethanamide. </p><p> Amides that have additional substituents on the nitrogen are treated similarly to the case of amines: they are ordered alphabetically with the location prefix <i>N</i>: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCON(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> is <i>N</i>,<i>N</i>-dimethylmethanamide, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CON(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> is <i>N</i>,<i>N</i>-dimethylethanamide.</p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Nitriles">Nitriles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=21" title="Edit section: Nitriles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Nitrile_Structural_Formulae_V.1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/220px-Nitrile_Structural_Formulae_V.1.png" decoding="async" width="220" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/330px-Nitrile_Structural_Formulae_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/440px-Nitrile_Structural_Formulae_V.1.png 2x" data-file-width="1017" data-file-height="220" /></a><figcaption></figcaption></figure> <p>Nitriles (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C≡N</span>) are named by adding the suffix "-nitrile" to the longest hydrocarbon chain (including the carbon of the cyano group). It can also be named by replacing the "-oic acid" of their corresponding carboxylic acids with "-carbonitrile." The prefix form is "cyano-." Functional class IUPAC nomenclature may also be used in the form of alkyl cyanides. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>C≡N</span> is called pentanenitrile or butyl cyanide. </p> <div class="mw-heading mw-heading3"><h3 id="Cyclic_compounds">Cyclic compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=22" title="Edit section: Cyclic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:IUPAC-cyclic.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/446px-IUPAC-cyclic.svg.png" decoding="async" width="446" height="184" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/669px-IUPAC-cyclic.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/892px-IUPAC-cyclic.svg.png 2x" data-file-width="446" data-file-height="184" /></a><figcaption></figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Bicyclic_molecule#Nomenclature" title="Bicyclic molecule">Bicyclic molecule § Nomenclature</a></div> <p><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a> and <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> compounds can be treated as the main parent chain of the compound, in which case the positions of substituents are numbered around the ring structure. For example, the three isomers of <a href="/wiki/Xylene" title="Xylene">xylene</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>CH<sub class="template-chem2-sub">3</sub></span>, commonly the <i>ortho-</i>, <i><a href="/wiki/Meta-_(chemistry)" class="mw-redirect" title="Meta- (chemistry)">meta-</a></i>, and <i>para-</i> forms, are 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene. The cyclic structures can also be treated as functional groups themselves, in which case they take the prefix "cyclo<i>alkyl</i>-" (e.g. "cyclohexyl-") or for benzene, "phenyl-". </p><p>The IUPAC nomenclature scheme becomes rapidly more elaborate for more complex cyclic structures, with notation for compounds containing conjoined rings, and many common names such as <a href="/wiki/Phenol" title="Phenol">phenol</a> being accepted as base names for compounds derived from them. </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Order_of_precedence_of_group">Order of precedence of group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=23" title="Edit section: Order of precedence of group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When compounds contain more than one functional group, the order of precedence determines which groups are named with prefix or suffix forms. The table below shows common groups in decreasing order of precedence. The highest-precedence group takes the suffix, with all others taking the prefix form. However, double and triple bonds only take suffix form (-en and -yn) and are used with other suffixes. </p><p>Prefixed substituents are ordered alphabetically (excluding any modifiers such as di-, tri-, etc.), e.g. chlorofluoromethane, <i>not</i> fluorochloromethane. If there are multiple functional groups of the same type, either prefixed or suffixed, the position numbers are ordered numerically (thus ethane-1,2-diol, <i>not</i> ethane-2,1-diol.) The <i>N</i> position indicator for amines and amides comes before "1", e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH(CH<sub class="template-chem2-sub">3</sub>)CH<sub class="template-chem2-sub">2</sub>NH(CH<sub class="template-chem2-sub">3</sub>)</span> is <i>N</i>,2-dimethylpropanamine. </p> <table class="wikitable"> <tbody><tr> <th>Priority </th> <th><a href="/wiki/Functional_group" title="Functional group">Functional group</a> </th> <th><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a> </th> <th>Prefix </th> <th>Suffix </th></tr> <tr> <td>1 </td> <td><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> <dl><dd>e.g. <a href="/wiki/Ammonium" title="Ammonium">Ammonium</a></dd></dl> </td> <td><br /> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>+</span><span>4</span></span></span></dd></dl> </td> <td>-onio- <dl><dd>ammonio-</dd></dl> </td> <td>-onium <dl><dd>-ammonium</dd></dl> </td></tr> <tr> <td>2 </td> <td><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acids</a> <dl><dd><a href="/wiki/Thiocarboxylic_acid" title="Thiocarboxylic acid">Carbothioic <i>S</i>-acids</a></dd> <dd><a href="/w/index.php?title=Carboselenoic_acid&action=edit&redlink=1" class="new" title="Carboselenoic acid (page does not exist)">Carboselenoic <i>Se</i>-acids</a></dd> <dd><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acids</a></dd> <dd><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acids</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COOH</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COSH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COSeH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SO<sub class="template-chem2-sub">3</sub>H</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> </td> <td>carboxy- <dl><dd>sulfanylcarbonyl-</dd> <dd>selanylcarbonyl-</dd> <dd>sulfo-</dd> <dd>sulfino-</dd></dl> </td> <td>-oic acid* <dl><dd>-thioic <i>S</i>-acid*</dd> <dd>-selenoic <i>Se</i>-acid*</dd> <dd>-sulfonic acid</dd> <dd>-sulfinic acid</dd></dl> </td></tr> <tr> <td>3 </td> <td><i>Carboxylic acid derivatives</i> <dl><dd><a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">Acid anhydride</a> <dl><dd><a href="/wiki/Ester" title="Ester">Esters</a></dd> <dd><a href="/wiki/Acyl_halides" class="mw-redirect" title="Acyl halides">Acyl halides</a></dd> <dd><a href="/wiki/Amide" title="Amide">Amides</a></dd> <dd><a href="/wiki/Imide" title="Imide">Imides</a></dd> <dd><a href="/wiki/Amidine" title="Amidine">Amidines</a></dd></dl></dd></dl> </td> <td><br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COOCO−</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COO−</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COX</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CONH<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CONC<</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CNHNH<sub class="template-chem2-sub">2</sub></span></dd></dl> </td> <td><br /> acyloxy- <dl><dd>R-oxycarbonyl-</dd> <dd>halocarbonyl-</dd> <dd>carbamoyl-</dd> <dd>-imido-</dd> <dd>amidino-</dd></dl> </td> <td><br />-R-oic anhydride <dl><dd>-R-oate</dd> <dd>-oyl halide*</dd> <dd>-amide*</dd> <dd>-imide*</dd> <dd>-amidine*</dd></dl> </td></tr> <tr> <td>4 </td> <td><a href="/wiki/Nitrile" title="Nitrile">Nitriles</a> <dl><dd><a href="/wiki/Isocyanide" title="Isocyanide">Isocyanides</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CN</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−NC</span></dd></dl> </td> <td>cyano- <dl><dd>isocyano-</dd></dl> </td> <td>-nitrile* <dl><dd>isocyanide</dd></dl> </td></tr> <tr> <td>5 </td> <td><a href="/wiki/Aldehyde" title="Aldehyde">Aldehydes</a> <dl><dd><a href="/wiki/Thioaldehyde" class="mw-redirect" title="Thioaldehyde">Thioaldehydes</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CHO</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CHS</span></dd></dl> </td> <td>formyl- <dl><dd>thioformyl-</dd></dl> </td> <td>-al* <dl><dd>-thial*</dd></dl> </td></tr> <tr> <td>6 </td> <td><a href="/wiki/Ketone" title="Ketone">Ketones</a> <dl><dd><a href="/wiki/Thioketone" title="Thioketone">Thioketones</a></dd> <dd><a href="/wiki/Selone" title="Selone">Selones</a></dd> <dd><a href="/w/index.php?title=Tellone&action=edit&redlink=1" class="new" title="Tellone (page does not exist)">Tellones</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=O</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=S</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=Se</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=Te</span></dd></dl> </td> <td>oxo- <dl><dd>sulfanylidene-</dd> <dd>selanylidene-</dd> <dd>tellanylidene-</dd></dl> </td> <td>-one <dl><dd>-thione</dd> <dd>-selone</dd> <dd>-tellone</dd></dl> </td></tr> <tr> <td>7 </td> <td><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> <dl><dd><a href="/wiki/Thiol" title="Thiol">Thiols</a></dd> <dd><a href="/wiki/Selenol" title="Selenol">Selenols</a></dd> <dd><a href="/wiki/Tellurol" title="Tellurol">Tellurols</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SeH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−TeH</span></dd></dl> </td> <td>hydroxy- <dl><dd>sulfanyl-</dd> <dd>selanyl-</dd> <dd>tellanyl-</dd></dl> </td> <td>-ol <dl><dd>-thiol</dd> <dd>-selenol</dd> <dd>-tellurol</dd></dl> </td></tr> <tr> <td>8 </td> <td><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxides</a> <dl><dd><a href="/wiki/Peroxols" class="mw-redirect" title="Peroxols">Peroxols</a></dd> <dd><a href="/w/index.php?title=Thioperoxols&action=edit&redlink=1" class="new" title="Thioperoxols (page does not exist)">Thioperoxols</a> (<a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a>)</dd> <dd><a href="/w/index.php?title=Dithioperoxols&action=edit&redlink=1" class="new" title="Dithioperoxols (page does not exist)">Dithioperoxols</a></dd></dl> </td> <td><br /> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OOH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SOH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−SSH</span></dd></dl> </td> <td><br /> <dl><dd>hydroperoxy-</dd> <dd>hydroxysulfanyl-</dd> <dd>disulfanyl-</dd></dl> </td> <td><br /> <dl><dd>-peroxol</dd> <dd>-<i>SO</i>-thioperoxol</dd> <dd>-dithioperoxol</dd></dl> </td></tr> <tr> <td>9 </td> <td><a href="/wiki/Amine" title="Amine">Amines</a> <dl><dd><a href="/wiki/Imine" title="Imine">Imines</a></dd> <dd><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a></dd></dl> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−NH<sub class="template-chem2-sub">2</sub></span> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=NH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−NHNH<sub class="template-chem2-sub">2</sub></span></dd></dl> </td> <td>amino- <dl><dd>imino-</dd> <dd>hydrazino-</dd></dl> </td> <td>-amine <dl><dd>-imine</dd> <dd>-hydrazine</dd></dl> </td></tr></tbody></table> <p><small>*<i>Note</i>: These suffixes, in which the carbon atom is counted as part of the preceding chain, are the most commonly used. See individual functional group articles for more details.</small> </p><p>The order of remaining functional groups is only needed for substituted benzene and hence is not mentioned here.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (February 2016)">clarification needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Common_nomenclature_–_trivial_names"><span id="Common_nomenclature_.E2.80.93_trivial_names"></span>Common nomenclature – trivial names</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=24" title="Edit section: Common nomenclature – trivial names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common nomenclature uses the older names for some organic compounds instead of using the prefixes for the carbon skeleton above. The pattern can be seen below. </p> <table class="wikitable"> <tbody><tr> <th>Number of<br />carbons</th> <th>Prefix as in<br />new system</th> <th>Common name<br />for alcohol</th> <th>Common name<br />for aldehyde</th> <th>Common name<br />for acid </th> <th>Common name<br />for ketone </th></tr> <tr> <td>1</td> <td>Meth-</td> <td><b>Meth</b>yl alcohol<br />(wood alcohol)</td> <td><b>Form</b>aldehyde</td> <td><b>Form</b>ic acid </td> <td>NA </td></tr> <tr> <td>2</td> <td>Eth-</td> <td><b>Eth</b>yl alcohol<br />(grain alcohol)</td> <td><b>Acet</b>aldehyde</td> <td><b>Acet</b>ic acid (vinegar) </td> <td>NA </td></tr> <tr> <td>3</td> <td>Prop-</td> <td><b>Prop</b>yl alcohol</td> <td><b>Propion</b>aldehyde</td> <td><b>Propion</b>ic acid </td> <td><b>Acet</b>one/<b>dimethyl</b> ketone </td></tr> <tr> <td>4</td> <td>But-</td> <td><b>But</b>yl alcohol</td> <td><b>Butyr</b>aldehyde</td> <td><b>Butyr</b>ic acid </td> <td><b>Methyl ethyl</b> ketone </td></tr> <tr> <td>5</td> <td>Pent-</td> <td><b>Am</b>yl alcohol</td> <td><b>Valer</b>aldehyde</td> <td><b>Valer</b>ic acid </td> <td><b>•Methyl propyl</b> ketone <p><b>•Diethyl</b> ketone </p> </td></tr> <tr> <td>6</td> <td>Hex-</td> <td><b>Capro</b>yl alcohol</td> <td><b>Capro</b>aldehyde</td> <td><b>Capro</b>ic acid </td> <td><b>•Butyl methyl</b> ketone <p><b>•Ethyl propyl</b> ketone </p> </td></tr> <tr> <td>7</td> <td>Hept-</td> <td><b>Enanth</b>yl alcohol</td> <td><b>Enanth</b>aldehyde</td> <td><b>Enanth</b>oic acid </td> <td><b>•Methyl pentyl</b> ketone <p><b>•Butyl ethyl</b> ketone </p><p><b>•Dipropyl</b> ketone </p> </td></tr> <tr> <td>8</td> <td>Oct-</td> <td><b>Capr</b>yl alcohol</td> <td><b>Capryl</b>aldehyde</td> <td><b>Capryl</b>ic acid </td> <td><b>•Hexyl methyl</b> ketone <p><b>•Ethyl pentyl</b> ketone </p><p><b>•Butyl propyl</b> ketone </p> </td></tr> <tr> <td>9</td> <td>Non-</td> <td><b>Pelargon</b>ic alcohol</td> <td><b>Pelargon</b>aldehyde</td> <td><b>Pelargon</b>ic acid </td> <td><b>•Heptyl methyl</b> ketone <p><b>•Ethyl hexyl</b> ketone </p><p><b>•Pentyl propyl</b> ketone </p><p><b>•Dibutyl</b> ketone </p> </td></tr> <tr> <td>10</td> <td>Dec-</td> <td><b>Capr</b>ic alcohol</td> <td><b>Capr</b>aldehyde</td> <td><b>Capr</b>ic acid </td> <td><b>•Methyl octyl</b> ketone <p><b>•Ethyl heptyl</b> ketone </p><p><b>•Hexyl propyl</b> ketone </p><p><b>•Butyl pentyl</b> ketone </p> </td></tr> <tr> <td>11</td> <td>Undec-</td> <td>-</td> <td>-</td> <td>- </td> <td rowspan="30"><i>The same pattern continues</i> <p><i>(<a class="mw-selflink-fragment" href="#Ketones_2">see below</a>)</i> </p> </td></tr> <tr> <td>12</td> <td>Dodec-</td> <td><b>Laur</b>yl alcohol</td> <td><b>Laur</b>aldehyde</td> <td><b>Laur</b>ic acid </td></tr> <tr> <td>13</td> <td>Tridec-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>14</td> <td>Tetradec-</td> <td><b>Myrist</b>yl alcohol</td> <td><b>Myrist</b>aldehyde</td> <td><b>Myrist</b>ic acid </td></tr> <tr> <td>15</td> <td>Pentadec-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>16</td> <td>Hexadec-</td> <td><b>Cet</b>yl alcohol<br /><b>Palmit</b>yl alcohol</td> <td><b>Palmit</b>aldehyde</td> <td><b>Palmit</b>ic acid </td></tr> <tr> <td>17</td> <td>Heptadec-</td> <td>-</td> <td>-</td> <td><b>Margar</b>ic acid </td></tr> <tr> <td>18</td> <td>Octadec-</td> <td><b>Stear</b>yl alcohol</td> <td><b>Stear</b>aldehyde</td> <td><b>Stear</b>ic acid </td></tr> <tr> <td>19</td> <td>Nonadec-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>20</td> <td>Icos-</td> <td><b>Arachid</b>yl alcohol</td> <td>-</td> <td><b>Arachid</b>ic acid </td></tr> <tr> <td>21</td> <td>Henicos-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>22</td> <td>Docos-</td> <td><b>Behen</b>yl alcohol</td> <td>-</td> <td><b>Behen</b>ic acid </td></tr> <tr> <td>23</td> <td>Tricos-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>24</td> <td>Tetracos-</td> <td><b>Lignocer</b>yl alcohol</td> <td>-</td> <td><b>Lignocer</b>ic acid </td></tr> <tr> <td>25</td> <td>Pentacos-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>26</td> <td>Hexacos-</td> <td><b>Cer</b>yl alcohol</td> <td>-</td> <td><b>Cerot</b>ic acid </td></tr> <tr> <td>27</td> <td>Heptacos-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>28</td> <td>Octacos-</td> <td><b>Montan</b>yl alcohol</td> <td>-</td> <td><b>Montan</b>ic acid </td></tr> <tr> <td>29</td> <td>Nonacos-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>30</td> <td>Triacont-</td> <td><b>Meliss</b>yl alcohol</td> <td>-</td> <td><b>Meliss</b>ic acid </td></tr> <tr> <td>31</td> <td>Hentriacont-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>32</td> <td>Dotriacont-</td> <td><b>Laccer</b>yl alcohol</td> <td>-</td> <td><b>Laccer</b>oic acid </td></tr> <tr> <td>33</td> <td>Tritriacont-</td> <td><b>Psyll</b>ic alcohol</td> <td>-</td> <td><b>Psyll</b>ic acid </td></tr> <tr> <td>34</td> <td>Tetratriacont-</td> <td><b>Gedd</b>yl alcohol</td> <td>-</td> <td><b>Gedd</b>ic acid </td></tr> <tr> <td>35</td> <td>Pentatriacont-</td> <td>-</td> <td>-</td> <td><b>Ceroplast</b>ic acid </td></tr> <tr> <td>36</td> <td>Hexatriacont-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>37</td> <td>Heptatriacont-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>38</td> <td>Octatriacont-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>39</td> <td>Nonatriacont-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <td>40</td> <td>Tetracont-</td> <td>-</td> <td>-</td> <td>- </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Ketones_2">Ketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=25" title="Edit section: Ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common names for <a href="/wiki/Ketone" title="Ketone">ketones</a> can be derived by naming the two <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> groups bonded to the <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a> as separate words followed by the word <i>ketone</i>. </p> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Benzophenone" title="Benzophenone">Benzophenone</a></li> <li><a href="/wiki/Ethyl_isopropyl_ketone" title="Ethyl isopropyl ketone">Ethyl isopropyl ketone</a></li> <li><a href="/wiki/Diethyl_ketone" class="mw-redirect" title="Diethyl ketone">Diethyl ketone</a></li></ul> <p>The first three of the names shown above are still considered to be <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_701.htm">acceptable IUPAC names</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Aldehydes_2">Aldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=26" title="Edit section: Aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The common name for an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> is derived from the common name of the corresponding <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> by dropping the word <i>acid</i> and changing the suffix from -ic or -oic to -aldehyde. </p> <ul><li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Ions">Ions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=27" title="Edit section: Ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The IUPAC nomenclature also provides rules for naming <a href="/wiki/Ion" title="Ion">ions</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Hydron">Hydron</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=28" title="Edit section: Hydron"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">Hydron</a> is a generic term for hydrogen cation; protons, deuterons and tritons are all hydrons. The hydrons are not found in heavier isotopes, however. </p> <div class="mw-heading mw-heading3"><h3 id="Parent_hydride_cations">Parent hydride cations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=29" title="Edit section: Parent hydride cations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Onium_compounds" class="mw-redirect" title="Onium compounds">Onium compounds</a></div> <p>Simple cations formed by adding a <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">hydron</a> to a hydride of a halogen, <a href="/wiki/Chalcogen" title="Chalcogen">chalcogen</a> or <a href="/wiki/Pnictogen" title="Pnictogen">pnictogen</a> are named by adding the suffix "-onium" to the element's root: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">4</sub>N<sup class="template-chem2-sup">+</sup></span> is ammonium, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup></span> is oxonium, and H<sub>2</sub>F<sup>+</sup> is fluoronium. Ammonium was adopted instead of nitronium, which commonly refers to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>+</span><span>2</span></span></span>. </p><p>If the cationic center of the hydride is not a halogen, chalcogen or pnictogen then the suffix "-ium" is added to the name of the neutral hydride after dropping any final 'e'. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">5</sub>C<sup class="template-chem2-sup">+</sup></span> is methanium, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HO−(O<sup class="template-chem2-sup">+</sup>)H<sub class="template-chem2-sub">2</sub></span> is dioxidanium (HO-OH is dioxidane), and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>N<sup class="template-chem2-sup">−</sup>(N<sup class="template-chem2-sup">+</sup>)H<sub class="template-chem2-sub">3</sub></span> is diazanium (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>N−NH<sub class="template-chem2-sub">2</sub></span> is diazane). </p> <div class="mw-heading mw-heading3"><h3 id="Cations_and_substitution">Cations and substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=30" title="Edit section: Cations and substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The above cations except for methanium are not, strictly speaking, organic, since they do not contain carbon. However, many organic cations are obtained by substituting another element or some functional group for a hydrogen. </p><p>The name of each substitution is prefixed to the hydride cation name. If many substitutions by the same functional group occur, then the number is indicated by prefixing with "di-", "tri-" as with halogenation. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup></span> is trimethyloxonium. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>F<sub class="template-chem2-sub">3</sub>N<sup class="template-chem2-sup">+</sup></span> is trifluoromethylammonium. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=31" title="Edit section: See also"><span>edit</span></a><span 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class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=32" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration 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.cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFThe_Commission_on_the_Nomenclature_of_Organic_Chemistry_Varun_kedia1971" class="citation book cs1">The Commission on the Nomenclature of Organic Chemistry Varun kedia (1971) [1958 (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965 (C: Characteristic Groups)]. <i>Nomenclature of Organic Chemistry</i> (3rd edition combined ed.). London: Butterworths. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-408-70144-7" title="Special:BookSources/0-408-70144-7"><bdi>0-408-70144-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry&rft.place=London&rft.edition=3rd+edition+combined&rft.pub=Butterworths&rft.date=1971&rft.isbn=0-408-70144-7&rft.au=The+Commission+on+the+Nomenclature+of+Organic+Chemistry+Varun+kedia&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/BlueBook/PDF/BlueBookV2.pdf"><i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013</i></a> <span class="cs1-format">(PDF)</span>. Henri A. Favre, Warren H. Powell, International Union of Pure and Applied Chemistry. Cambridge, England: Royal Society of Chemistry. 2014. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84973-306-9" title="Special:BookSources/978-1-84973-306-9"><bdi>978-1-84973-306-9</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/865143943">865143943</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013&rft.place=Cambridge%2C+England&rft.pub=Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Aoclcnum%2F865143943&rft.isbn=978-1-84973-306-9&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2FBlueBook%2FPDF%2FBlueBookV2.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: others (<a href="/wiki/Category:CS1_maint:_others" title="Category:CS1 maint: others">link</a>)</span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://iupac.org/what-we-do/books/bluebook/">"Blue Book"</a>. <i>IUPAC | International Union of Pure and Applied Chemistry</i><span class="reference-accessdate">. Retrieved <span class="nowrap">19 September</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=IUPAC+%7C+International+Union+of+Pure+and+Applied+Chemistry&rft.atitle=Blue+Book&rft_id=https%3A%2F%2Fiupac.org%2Fwhat-we-do%2Fbooks%2Fbluebook%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/BriefGuide/inorganic.html">"Brief Guide to Inorganic Nomenclature"</a>. <i>iupac.qmul.ac.uk</i><span class="reference-accessdate">. Retrieved <span class="nowrap">19 September</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=iupac.qmul.ac.uk&rft.atitle=Brief+Guide+to+Inorganic+Nomenclature&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2FBriefGuide%2Finorganic.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHellwichHartshornYerinDamhus2020" class="citation journal cs1">Hellwich, Karl-Heinz; Hartshorn, Richard M.; Yerin, Andrey; Damhus, Ture; Hutton, Alan T. (1 March 2020). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fpac-2019-0104">"Brief guide to the nomenclature of organic chemistry (IUPAC Technical Report)"</a>. <i>Pure and Applied Chemistry</i>. <b>92</b> (3): 527–539. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fpac-2019-0104">10.1515/pac-2019-0104</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1365-3075">1365-3075</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+and+Applied+Chemistry&rft.atitle=Brief+guide+to+the+nomenclature+of+organic+chemistry+%28IUPAC+Technical+Report%29&rft.volume=92&rft.issue=3&rft.pages=527-539&rft.date=2020-03-01&rft_id=info%3Adoi%2F10.1515%2Fpac-2019-0104&rft.issn=1365-3075&rft.aulast=Hellwich&rft.aufirst=Karl-Heinz&rft.au=Hartshorn%2C+Richard+M.&rft.au=Yerin%2C+Andrey&rft.au=Damhus%2C+Ture&rft.au=Hutton%2C+Alan+T.&rft_id=https%3A%2F%2Fdoi.org%2F10.1515%252Fpac-2019-0104&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chem.ucalgary.ca/courses/351/orgnom/ethers/ethers-01.html">"Basic IUPAC Organic Nomenclature"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Basic+IUPAC+Organic+Nomenclature&rft_id=http%3A%2F%2Fwww.chem.ucalgary.ca%2Fcourses%2F351%2Forgnom%2Fethers%2Fethers-01.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry_Organic_Chemistry_Division_Commission_on_Nomenclature_of_Organic_Chemistry1995" class="citation book cs1"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> Organic Chemistry Division Commission on Nomenclature of Organic Chemistry (1995). <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_705.htm">"Table 28(a): Carboxylic acids and related group"</a>. In Panico, Robert; Powell, Warren H.; Richer, Jean-Claude (eds.). <i>A Guide to IUPAC Nomenclature of Organic Compounds: Recommendations 1993 (including revisions, published and hitherto unpublished, to the 1979 edition of Nomenclature of Organic Chemistry)</i> (2nd ed.). Oxford: <a href="/wiki/Blackwell_Scientific_Publications" class="mw-redirect" title="Blackwell Scientific Publications">Blackwell Scientific Publications</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780632034888" title="Special:BookSources/9780632034888"><bdi>9780632034888</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Table+28%28a%29%3A+Carboxylic+acids+and+related+group&rft.btitle=A+Guide+to+IUPAC+Nomenclature+of+Organic+Compounds%3A+Recommendations+1993+%28including+revisions%2C+published+and+hitherto+unpublished%2C+to+the+1979+edition+of+Nomenclature+of+Organic+Chemistry%29&rft.place=Oxford&rft.edition=2nd&rft.pub=Blackwell+Scientific+Publications&rft.date=1995&rft.isbn=9780632034888&rft.au=International+Union+of+Pure+and+Applied+Chemistry+Organic+Chemistry+Division+Commission+on+Nomenclature+of+Organic+Chemistry&rft_id=http%3A%2F%2Fwww.acdlabs.com%2Fiupac%2Fnomenclature%2F93%2Fr93_705.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading3"><h3 id="Bibliography">Bibliography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=33" title="Edit section: Bibliography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFavrePowell2013" class="citation book cs1">Favre, Henri A.; Powell, Warren H. (2013). <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013</i>. <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pub=Royal+Society+of+Chemistry&rft.date=2013&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=Henri+A.&rft.au=Powell%2C+Warren+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=IUPAC_nomenclature_of_organic_chemistry&action=edit&section=34" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/">IUPAC Nomenclature of Organic Chemistry</a> (online version of several older editions of the <a href="/wiki/IUPAC_Blue_Book" class="mw-redirect" title="IUPAC Blue Book">IUPAC Blue Book</a>)</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20051102095104/http://www.chem.qmul.ac.uk/iupac/">IUPAC Recommendations on Organic & Biochemical Nomenclature, Symbols, Terminology, etc.</a> (includes IUBMB Recommendations for biochemistry)</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060105051351/http://www.chem.qmul.ac.uk/iupac/bibliog/cnoc.html">Bibliography of IUPAC Recommendations on Organic Nomenclature</a> (last updated 11 April 2003)</li> <li><a rel="nofollow" class="external text" href="http://www.acdlabs.com/products/draw_nom/nom/name/">ACD/Name</a> Software for generating systematic nomenclature</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20101124182810/http://www.chemaxon.com/products/name-to-structure/">ChemAxon Name <> Structure</a> – ChemAxon IUPAC (& traditional) name to structure and structure to IUPAC name software. As used at <a rel="nofollow" class="external text" href="http://www.chemicalize.org">chemicalize.org</a></li> <li><a rel="nofollow" class="external text" href="http://www.chemicalize.org">chemicalize.org</a> A free web site/service that extracts IUPAC names from web pages and annotates a 'chemicalized' version with structure images. Structures from annotated pages can also be searched.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEller2006" class="citation journal cs1">Eller, Gernot A. (2006). <a rel="nofollow" class="external text" href="http://www.mdpi.org/molecules/papers/11110915.pdf">"Improving the Quality of Published Chemical Names with Nomenclature Software"</a> <span class="cs1-format">(PDF)</span>. <i><a href="/wiki/Molecules_(journal)" title="Molecules (journal)">Molecules</a></i>. <b>9</b> (11): 915–928. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2F11110915">10.3390/11110915</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6148558">6148558</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18007396">18007396</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecules&rft.atitle=Improving+the+Quality+of+Published+Chemical+Names+with+Nomenclature+Software&rft.volume=9&rft.issue=11&rft.pages=915-928&rft.date=2006&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6148558%23id-name%3DPMC&rft_id=info%3Apmid%2F18007396&rft_id=info%3Adoi%2F10.3390%2F11110915&rft.aulast=Eller&rft.aufirst=Gernot+A.&rft_id=http%3A%2F%2Fwww.mdpi.org%2Fmolecules%2Fpapers%2F11110915.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIUPAC+nomenclature+of+organic+chemistry" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="https://archive.today/20130223063758/http://portal.acs.org/portal/PublicWebSite/about/governance/committees/nomenclature/index.htm">American Chemical Society, Committee on Nomenclature, Terminology & Symbols</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeighFavreMetanomski1998" class="citation book cs1">Leigh, G. J.; Favre, H. A.; Metanomski, W. V. (1998). <a rel="nofollow" class="external text" href="http://old.iupac.org/publications/books/principles/principles_of_nomenclature.pdf"><i>Principles of Chemical Nomenclature. A Guide to IUPAC Recommendations</i></a> <span class="cs1-format">(PDF)</span>. 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