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</div> </a> <ul id="toc-Boiling_points-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Odour" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Odour"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Odour</span> </div> </a> <ul id="toc-Odour-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Characterization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Characterization"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Characterization</span> </div> </a> <ul id="toc-Characterization-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence_and_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence_and_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Occurrence and applications</span> </div> </a> <ul id="toc-Occurrence_and_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-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 Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Industrial_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Industrial routes</span> </div> </a> <ul id="toc-Industrial_routes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Laboratory methods</span> </div> </a> <ul id="toc-Laboratory_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Less-common_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Less-common_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Less-common reactions</span> </div> </a> <ul id="toc-Less-common_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Acid-base_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid-base_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Acid-base reactions</span> </div> </a> <ul id="toc-Acid-base_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_esters,_amides,_anhydrides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_esters,_amides,_anhydrides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Conversion to esters, amides, anhydrides</span> </div> </a> <ul id="toc-Conversion_to_esters,_amides,_anhydrides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_acyl_halides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_acyl_halides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Conversion to acyl halides</span> </div> </a> <ul id="toc-Conversion_to_acyl_halides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions_with_carbanion_equivalents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions_with_carbanion_equivalents"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Reactions with carbanion equivalents</span> </div> </a> <ul id="toc-Reactions_with_carbanion_equivalents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Specialized_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Specialized_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Specialized reactions</span> </div> </a> <ul id="toc-Specialized_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Carboxyl_radical" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Carboxyl_radical"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Carboxyl radical</span> </div> </a> <ul id="toc-Carboxyl_radical-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <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">Carboxylic acid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 79 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-79" 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">79 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/Karboksielsuur" title="Karboksielsuur – Afrikaans" lang="af" hreflang="af" data-title="Karboksielsuur" 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%AD%D9%85%D8%B6_%D9%83%D8%B1%D8%A8%D9%88%D9%83%D8%B3%D9%8A%D9%84%D9%8A" title="حمض كربوكسيلي – Arabic" lang="ar" hreflang="ar" data-title="حمض كربوكسيلي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu_carbox%C3%ADlico" title="Ácidu carboxílico – Asturian" lang="ast" hreflang="ast" data-title="Ácidu carboxílico" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Karbon_tur%C5%9Fular%C4%B1" title="Karbon turşuları – Azerbaijani" lang="az" hreflang="az" data-title="Karbon turşuları" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%DA%A9%D8%B3%DB%8C%D9%84%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کربوکسیلیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="کربوکسیلیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%95%E0%A6%BE%E0%A6%B0%E0%A7%8D%E0%A6%AC%E0%A6%95%E0%A7%8D%E0%A6%B8%E0%A6%BF%E0%A6%B2%E0%A6%BF%E0%A6%95_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="কার্বক্সিলিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="কার্বক্সিলিক অ্যাসিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B0%D0%B2%D1%8B%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Карбонавыя кіслоты – Belarusian" lang="be" hreflang="be" data-title="Карбонавыя кіслоты" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B0%D0%B2%D1%8B%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%96" title="Карбонавыя кісьлі – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Карбонавыя кісьлі" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Asidong_karboksiliko" title="Asidong karboksiliko – Central Bikol" lang="bcl" hreflang="bcl" data-title="Asidong karboksiliko" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Карбоксилна киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Карбоксилна киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Karboksilna_kiselina" title="Karboksilna kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Karboksilna kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_carbox%C3%ADlic" title="Àcid carboxílic – Catalan" lang="ca" hreflang="ca" data-title="Àcid carboxílic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD_%D0%B9%D3%B3%C3%A7%D0%B5%D0%BA%C4%95" title="Карбон йӳçекĕ – Chuvash" lang="cv" hreflang="cv" data-title="Карбон йӳçекĕ" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Karboxylov%C3%A9_kyseliny" title="Karboxylové kyseliny – Czech" lang="cs" hreflang="cs" data-title="Karboxylové kyseliny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid_carbocsylig" title="Asid carbocsylig – Welsh" lang="cy" hreflang="cy" data-title="Asid carbocsylig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Carboxylsyre" title="Carboxylsyre – Danish" lang="da" hreflang="da" data-title="Carboxylsyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Carbons%C3%A4uren" title="Carbonsäuren – German" lang="de" hreflang="de" data-title="Carbonsäuren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Karboks%C3%BC%C3%BClhapped" title="Karboksüülhapped – Estonian" lang="et" hreflang="et" data-title="Karboksüülhapped" 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%9A%CE%B1%CF%81%CE%B2%CE%BF%CE%BE%CF%85%CE%BB%CE%B9%CE%BA%CE%AC_%CE%BF%CE%BE%CE%AD%CE%B1" title="Καρβοξυλικά οξέα – Greek" lang="el" hreflang="el" data-title="Καρβοξυλικά οξέα" 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/%C3%81cido_carbox%C3%ADlico" title="Ácido carboxílico – Spanish" lang="es" hreflang="es" data-title="Ácido carboxílico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Karboksilata_acido" title="Karboksilata acido – Esperanto" lang="eo" hreflang="eo" data-title="Karboksilata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_karboxiliko" title="Azido karboxiliko – Basque" lang="eu" hreflang="eu" data-title="Azido karboxiliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%DA%A9%D8%B3%DB%8C%D9%84%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کربوکسیلیک اسید – Persian" lang="fa" hreflang="fa" data-title="کربوکسیلیک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Carboxyls%C3%BDra" title="Carboxylsýra – Faroese" lang="fo" hreflang="fo" data-title="Carboxylsýra" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_carboxylique" title="Acide carboxylique – French" lang="fr" hreflang="fr" data-title="Acide carboxylique" 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/Aig%C3%A9ad_carbocsaileach" title="Aigéad carbocsaileach – Irish" lang="ga" hreflang="ga" data-title="Aigéad carbocsaileach" 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/%C3%81cido_carbox%C3%ADlico" title="Ácido carboxílico – Galician" lang="gl" hreflang="gl" data-title="Ácido carboxílico" 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%B9%B4%EB%B3%B5%EC%8B%A4%EC%82%B0" title="카복실산 – Korean" lang="ko" hreflang="ko" data-title="카복실산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Carboxylic_acid" title="Carboxylic acid – Hausa" lang="ha" hreflang="ha" data-title="Carboxylic acid" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A1%D6%80%D5%A2%D5%B8%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82%D5%B6%D5%A5%D6%80" title="Կարբոնաթթուներ – Armenian" lang="hy" hreflang="hy" data-title="Կարբոնաթթուներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A5%8B%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A4%BF%E0%A4%B2%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="कार्बोक्सिलिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="कार्बोक्सिलिक अम्ल" 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/Karboksilne_kiseline" title="Karboksilne kiseline – Croatian" lang="hr" hreflang="hr" data-title="Karboksilne kiseline" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_alkanoat" title="Asam alkanoat – Indonesian" lang="id" hreflang="id" data-title="Asam alkanoat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acidi_carbossilici" title="Acidi carbossilici – Italian" lang="it" hreflang="it" data-title="Acidi carbossilici" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%94_%D7%A7%D7%A8%D7%91%D7%95%D7%A7%D7%A1%D7%99%D7%9C%D7%99%D7%AA" title="חומצה קרבוקסילית – Hebrew" lang="he" hreflang="he" data-title="חומצה קרבוקסילית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D0%B4%D0%B0%D1%80%D1%8B" title="Карбон қышқылдары – Kazakh" lang="kk" hreflang="kk" data-title="Карбон қышқылдары" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D0%BB%D0%B0%D1%80%D1%8B" title="Карбон кислоталары – Kyrgyz" lang="ky" hreflang="ky" data-title="Карбон кислоталары" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_carboxylicum" title="Acidum carboxylicum – Latin" lang="la" hreflang="la" data-title="Acidum carboxylicum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Karbonsk%C4%81bes" title="Karbonskābes – Latvian" lang="lv" hreflang="lv" data-title="Karbonskābes" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Karboksir%C5%ABg%C5%A1tys" title="Karboksirūgštys – Lithuanian" lang="lt" hreflang="lt" data-title="Karboksirūgštys" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Karbonsavak" title="Karbonsavak – Hungarian" lang="hu" hreflang="hu" data-title="Karbonsavak" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Карбоксилна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Карбоксилна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%95%E0%B4%BE%E0%B5%BC%E0%B4%AC%E0%B5%8B%E0%B4%95%E0%B5%8D%E0%B4%B8%E0%B4%BF%E0%B4%B2%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%86%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="കാർബോക്സിലിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="കാർബോക്സിലിക് ആസിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_karboksilik" title="Asid karboksilik – Malay" lang="ms" hreflang="ms" data-title="Asid karboksilik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Carbonzuur" title="Carbonzuur – Dutch" lang="nl" hreflang="nl" data-title="Carbonzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%AB%E3%83%9C%E3%83%B3%E9%85%B8" title="カルボン酸 – Japanese" lang="ja" hreflang="ja" data-title="カルボン酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Karboksylsyre" title="Karboksylsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Karboksylsyre" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Karboksylsyre" title="Karboksylsyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Karboksylsyre" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Acid_carboxilic" title="Acid carboxilic – Occitan" lang="oc" hreflang="oc" data-title="Acid carboxilic" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Karbon_kislotalar" title="Karbon kislotalar – Uzbek" lang="uz" hreflang="uz" data-title="Karbon kislotalar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%95%E0%A8%BE%E0%A8%B0%E0%A8%AC%E0%A9%8C%E0%A8%95%E0%A8%B8%E0%A8%BF%E0%A8%B2%E0%A9%80_%E0%A8%A4%E0%A8%BF%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%AC" title="ਕਾਰਬੌਕਸਿਲੀ ਤਿਜ਼ਾਬ – Punjabi" lang="pa" hreflang="pa" data-title="ਕਾਰਬੌਕਸਿਲੀ ਤਿਜ਼ਾਬ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DA%A9%D8%A7%D8%B1%D8%A8%D9%88%DA%A9%D8%B3%D9%84%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="کاربوکسلک تیزاب – Western Punjabi" lang="pnb" hreflang="pnb" data-title="کاربوکسلک تیزاب" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwasy_karboksylowe" title="Kwasy karboksylowe – Polish" lang="pl" hreflang="pl" data-title="Kwasy karboksylowe" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_carbox%C3%ADlico" title="Ácido carboxílico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido carboxílico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_carboxilic" title="Acid carboxilic – Romanian" lang="ro" hreflang="ro" data-title="Acid carboxilic" 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%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%BE%D0%B2%D1%8B%D0%B5_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Карбоновые кислоты – Russian" lang="ru" hreflang="ru" data-title="Карбоновые кислоты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Derivatet_karboksilike" title="Derivatet karboksilike – Albanian" lang="sq" hreflang="sq" data-title="Derivatet karboksilike" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%9A%E0%B7%8F%E0%B6%B6%E0%B7%9C%E0%B6%9A%E0%B7%8A%E0%B7%83%E0%B7%92%E0%B6%BD%E0%B7%92%E0%B6%9A%E0%B7%8A_%E0%B6%85%E0%B6%B8%E0%B7%8A%E0%B6%BD%E0%B6%BA" title="කාබොක්සිලික් අම්ලය – Sinhala" lang="si" hreflang="si" data-title="කාබොක්සිලික් අම්ලය" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carboxylic_acid" title="Carboxylic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carboxylic acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Karboxylov%C3%A1_kyselina" title="Karboxylová kyselina – Slovak" lang="sk" hreflang="sk" data-title="Karboxylová kyselina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Karboksilna_kislina" title="Karboksilna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Karboksilna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%AA%D8%B1%D8%B4%DB%8C_%DA%A9%D8%A7%D8%B1%D8%A8%DB%86%DA%A9%D8%B3%DB%8C%D9%84%DB%8C" title="ترشی کاربۆکسیلی – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ترشی کاربۆکسیلی" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Карбоксилна киселина – Serbian" lang="sr" hreflang="sr" data-title="Карбоксилна киселина" 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/Karboksilna_kiselina" title="Karboksilna kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Karboksilna kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_karboksilat" title="Asam karboksilat – Sundanese" lang="su" hreflang="su" data-title="Asam karboksilat" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karboksyylihapot" title="Karboksyylihapot – Finnish" lang="fi" hreflang="fi" data-title="Karboksyylihapot" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Karboxylsyror" title="Karboxylsyror – Swedish" lang="sv" hreflang="sv" data-title="Karboxylsyror" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%AA%E0%AE%BE%E0%AE%95%E0%AF%8D%E0%AE%9A%E0%AE%BF%E0%AE%B2%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="கார்பாக்சிலிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="கார்பாக்சிலிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/Azeffar_aka%E1%B9%9Bbuksilin" title="Azeffar akaṛbuksilin – Kabyle" lang="kab" hreflang="kab" data-title="Azeffar akaṛbuksilin" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%95%E0%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%AC%E0%B1%8B%E0%B0%95%E0%B1%8D%E0%B0%B8%E0%B0%BF%E0%B0%B2%E0%B0%BF%E0%B0%95%E0%B1%8D_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="కార్బోక్సిలిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="కార్బోక్సిలిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%84%E0%B8%B2%E0%B8%A3%E0%B9%8C%E0%B8%9A%E0%B8%AD%E0%B8%81%E0%B8%8B%E0%B8%B4%E0%B8%A5%E0%B8%B4%E0%B8%81" title="กรดคาร์บอกซิลิก – Thai" lang="th" hreflang="th" data-title="กรดคาร์บอกซิลิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Karboksilik_asit" title="Karboksilik asit – Turkish" lang="tr" hreflang="tr" data-title="Karboksilik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%BE%D0%B2%D1%96_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B8" title="Карбонові кислоти – Ukrainian" lang="uk" hreflang="uk" data-title="Карбонові кислоти" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_carboxylic" title="Acid carboxylic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid carboxylic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li 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searchaux" style="display:none">Organic compound containing a –C(=O)OH group</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">"COOH" redirects here. For the Bulgarian DJ and producer Ivan Shopov, see <a href="/wiki/Cooh_(musician)" class="mw-redirect" title="Cooh (musician)">Cooh (musician)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Carbolic_acid" class="mw-redirect" title="Carbolic acid">Carbolic acid</a>.</div> <p class="mw-empty-elt"> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carboxylic-acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/150px-Carboxylic-acid.svg.png" decoding="async" width="150" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/225px-Carboxylic-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/300px-Carboxylic-acid.svg.png 2x" data-file-width="927" data-file-height="743" /></a><figcaption>Structure of a carboxylic acid</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carboxylate-resonance-hybrid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/150px-Carboxylate-resonance-hybrid.png" decoding="async" width="150" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/225px-Carboxylate-resonance-hybrid.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carboxylate-resonance-hybrid.png/300px-Carboxylate-resonance-hybrid.png 2x" data-file-width="806" data-file-height="742" /></a><figcaption>Carboxylate anion</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carboxyl-3D-space-filling-labelled.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Carboxyl-3D-space-filling-labelled.png/150px-Carboxyl-3D-space-filling-labelled.png" decoding="async" width="150" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Carboxyl-3D-space-filling-labelled.png/225px-Carboxyl-3D-space-filling-labelled.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Carboxyl-3D-space-filling-labelled.png/300px-Carboxyl-3D-space-filling-labelled.png 2x" data-file-width="1000" data-file-height="962" /></a><figcaption>3D structure of a carboxylic acid</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>carboxylic acid</b> is an <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a> that contains a <b>carboxyl group</b> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−C(=O)−OH</span>)<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> attached to an <a href="/wiki/Substituent" title="Substituent">R-group</a>. The general formula of a carboxylic acid is often written as <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−COOH</span></b> or <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CO<sub class="template-chem2-sub">2</sub>H</span></b>, sometimes as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(O)OH</span> with R referring to an <a href="/wiki/Organyl_group" title="Organyl group">organyl group</a> (e.g., <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a>, <a href="/wiki/Alkenyl" class="mw-redirect" title="Alkenyl">alkenyl</a>, <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>), or <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, or other groups. Carboxylic acids occur widely. Important examples include the <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> and <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>. <a href="/wiki/Deprotonation" title="Deprotonation">Deprotonation</a> of a carboxylic acid gives a <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Examples_and_nomenclature">Examples and nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=1" title="Edit section: Examples and nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids are commonly identified by their <a href="/wiki/Trivial_name" title="Trivial name">trivial names</a>. They often have the suffix <i>-ic acid</i>. <span class="anchor" id="-oic"></span><a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>-recommended names also exist; in this system, carboxylic acids have an <i>-oic acid</i> suffix.<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> For example, <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a> (<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>CO<sub class="template-chem2-sub">2</sub>H</span>) is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the <a href="/wiki/Parent_chain" class="mw-redirect" title="Parent chain">parent chain</a> even if there are other <a href="/wiki/Substituent" title="Substituent">substituents</a>, such as <a href="/wiki/3-chloropropanoic_acid" class="mw-redirect" title="3-chloropropanoic acid">3-chloropropanoic acid</a>. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another parent structure, such as <a href="/wiki/2-Furoic_acid" title="2-Furoic acid">2-carboxyfuran</a>. </p><p>The carboxylate anion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−COO<sup class="template-chem2-sup">−</sup></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CO<span class="template-chem2-su"><span>−</span><span>2</span></span></span>) of a carboxylic acid is usually named with the suffix <i>-ate</i>, in keeping with the general pattern of <i>-ic acid</i> and <i>-ate</i> for a <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate acid</a> and its conjugate base, respectively. For example, the conjugate base of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> is <a href="/wiki/Acetate" title="Acetate">acetate</a>. </p> <p><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a>, which occurs in <a href="/wiki/Bicarbonate_buffer_system" title="Bicarbonate buffer system">bicarbonate buffer systems</a> in nature, is not generally classed as one of the carboxylic acids, despite that it has a <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> that looks like a COOH group. <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style></p><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></span></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Carboxylic_acid" class="extiw" title="q:Special:Search/Carboxylic acid">Carboxylic acid</a></b></i>.</div></div> </div> <table class="wikitable"> <caption>Straight-chain, saturated carboxylic acids (alkanoic acids) </caption> <tbody><tr> <th>Carbon<br />atoms </th> <th>Common Name </th> <th>IUPAC Name </th> <th>Chemical formula </th> <th>Common location or use </th></tr> <tr> <td>1</td> <td><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></td> <td>Methanoic acid</td> <td>HCOOH</td> <td><a href="/wiki/Insect_stings" class="mw-redirect" title="Insect stings">Insect stings</a> </td></tr> <tr> <td>2</td> <td><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></td> <td>Ethanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH</span></td> <td><a href="/wiki/Vinegar" title="Vinegar">Vinegar</a> </td></tr> <tr> <td>3</td> <td><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic acid</a></td> <td>Propanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>COOH</span></td> <td>Preservative for stored grains, <a href="/wiki/Body_odour" class="mw-redirect" title="Body odour">body odour</a>, milk, butter, cheese </td></tr> <tr> <td>4</td> <td><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric acid</a></td> <td>Butanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>COOH</span></td> <td><a href="/wiki/Butter" title="Butter">Butter</a> </td></tr> <tr> <td>5</td> <td><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></td> <td>Pentanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>COOH</span></td> <td><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> plant </td></tr> <tr> <td>6</td> <td><a href="/wiki/Caproic_acid" title="Caproic acid">Caproic acid</a></td> <td>Hexanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">4</sub>COOH</span></td> <td><a href="/wiki/Goat" title="Goat">Goat</a> fat </td></tr> <tr> <td>7</td> <td><a href="/wiki/Enanthic_acid" title="Enanthic acid">Enanthic acid</a></td> <td>Heptanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">5</sub>COOH</span></td> <td>Fragrance </td></tr> <tr> <td>8</td> <td><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic acid</a></td> <td>Octanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">6</sub>COOH</span></td> <td><a href="/wiki/Coconuts" class="mw-redirect" title="Coconuts">Coconuts</a> </td></tr> <tr> <td>9</td> <td><a href="/wiki/Pelargonic_acid" title="Pelargonic acid">Pelargonic acid</a></td> <td>Nonanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">7</sub>COOH</span></td> <td><a href="/wiki/Pelargonium" title="Pelargonium">Pelargonium</a> plant </td></tr> <tr> <td>10</td> <td><a href="/wiki/Capric_acid" title="Capric acid">Capric acid</a></td> <td>Decanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">8</sub>COOH</span></td> <td><a href="/wiki/Coconut_oil" title="Coconut oil">Coconut</a> and <a href="/wiki/Palm_kernel_oil" title="Palm kernel oil">Palm kernel oil</a> </td></tr> <tr> <td>11</td> <td><a href="/wiki/Undecylic_acid" title="Undecylic acid">Undecylic acid</a></td> <td>Undecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">9</sub>COOH</span></td> <td>Anti-fungal agent </td></tr> <tr> <td>12</td> <td><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric acid</a></td> <td>Dodecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">10</sub>COOH</span></td> <td><a href="/wiki/Coconut_oil" title="Coconut oil">Coconut oil</a> and hand wash soaps </td></tr> <tr> <td>13</td> <td><a href="/wiki/Tridecylic_acid" title="Tridecylic acid">Tridecylic acid</a></td> <td>Tridecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">11</sub>COOH</span></td> <td>Plant metabolite </td></tr> <tr> <td>14</td> <td><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic acid</a></td> <td>Tetradecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">12</sub>COOH</span></td> <td><a href="/wiki/Nutmeg" title="Nutmeg">Nutmeg</a> </td></tr> <tr> <td>15</td> <td><a href="/wiki/Pentadecylic_acid" title="Pentadecylic acid">Pentadecylic acid</a></td> <td>Pentadecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">13</sub>COOH</span></td> <td>Milk fat </td></tr> <tr> <td>16</td> <td><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic acid</a></td> <td>Hexadecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">14</sub>COOH</span></td> <td><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a> </td></tr> <tr> <td>17</td> <td><a href="/wiki/Margaric_acid" title="Margaric acid">Margaric acid</a></td> <td>Heptadecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">15</sub>COOH</span></td> <td>Pheromone in various animals </td></tr> <tr> <td>18</td> <td><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic acid</a></td> <td>Octadecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">16</sub>COOH</span></td> <td><a href="/wiki/Chocolate" title="Chocolate">Chocolate</a>, waxes, soaps, and oils </td></tr> <tr> <td>19</td> <td><a href="/wiki/Nonadecylic_acid" title="Nonadecylic acid">Nonadecylic acid</a></td> <td>Nonadecanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">17</sub>COOH</span></td> <td>Fats, vegetable oils, <a href="/wiki/Pheromone" title="Pheromone">pheromone</a> </td></tr> <tr> <td>20</td> <td><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic acid</a></td> <td>Icosanoic acid</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">18</sub>COOH</span></td> <td><a href="/wiki/Peanut_oil" title="Peanut oil">Peanut oil</a> </td></tr></tbody></table> <table class="wikitable"> <caption>Other carboxylic acids </caption> <tbody><tr> <th>Compound class </th> <th>Members </th></tr> <tr> <td>unsaturated monocarboxylic acids</td> <td><a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a> (2-propenoic acid) – <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CH−COOH</span>, used in polymer synthesis </td></tr> <tr> <td><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a></td> <td>medium to long-chain saturated and unsaturated monocarboxylic acids, with even number of carbons; examples: <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a> and <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> (nutritional supplements) </td></tr> <tr> <td><a href="/wiki/Amino_acid" title="Amino acid">Amino acids</a></td> <td>the building-blocks of <a href="/wiki/Protein" title="Protein">proteins</a> </td></tr> <tr> <td><a href="/wiki/Keto_acid" title="Keto acid">Keto acids</a></td> <td>acids of biochemical significance that contain a <a href="/wiki/Ketone" title="Ketone">ketone</a> group; examples: <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetic acid</a> and <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> </td></tr> <tr> <td><a href="/wiki/Aromatic_compound" title="Aromatic compound">Aromatic</a> carboxylic acids</td> <td>containing at least one aromatic ring; examples: <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> – the sodium salt of benzoic acid is used as a food preservative; <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a> – a beta-hydroxy type found in many skin-care products; <a href="/wiki/Phenyl_alkanoic_acids" title="Phenyl alkanoic acids">phenyl alkanoic acids</a> – the class of compounds where a phenyl group is attached to a carboxylic acid </td></tr> <tr> <td><a href="/wiki/Dicarboxylic_acid" title="Dicarboxylic acid">Dicarboxylic acids</a></td> <td>containing two carboxyl groups; examples: <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a> the monomer used to produce <a href="/wiki/Nylon" title="Nylon">nylon</a> and <a href="/wiki/Aldaric_acid" title="Aldaric acid">aldaric acid</a> – a family of sugar acids </td></tr> <tr> <td><a href="/wiki/Tricarboxylic_acid" title="Tricarboxylic acid">Tricarboxylic acids</a></td> <td>containing three carboxyl groups; examples: <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a> – found in <a href="/wiki/Citrus_fruit" class="mw-redirect" title="Citrus fruit">citrus fruits</a> and <a href="/wiki/Isocitric_acid" title="Isocitric acid">isocitric acid</a> </td></tr> <tr> <td><a href="/wiki/Alpha_hydroxy_acid" class="mw-redirect" title="Alpha hydroxy acid">Alpha hydroxy acids</a></td> <td>containing a hydroxy group in the first position; examples: <a href="/wiki/Glyceric_acid" title="Glyceric acid">glyceric acid</a>, <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a> and <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> (2-hydroxypropanoic acid) – found in sour milk, <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a> – found in wine </td></tr> <tr> <td><a href="/wiki/Beta_hydroxy_acid" class="mw-redirect" title="Beta hydroxy acid">Beta hydroxy acids</a></td> <td>containing a hydroxy group in the second position </td></tr> <tr> <td><a href="/wiki/Omega_hydroxy_acid" title="Omega hydroxy acid">Omega hydroxy acids</a></td> <td>containing a hydroxy group beyond the first or second position </td></tr> <tr> <td><a href="/wiki/Divinylether_fatty_acids" title="Divinylether fatty acids">Divinylether fatty acids</a></td> <td>containing a doubly unsaturated carbon chain attached via an ether bond to a fatty acid, found in some plants </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=2" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Solubility">Solubility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=3" title="Edit section: Solubility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids are <a href="/wiki/Polarity_(chemistry)" class="mw-redirect" title="Polarity (chemistry)">polar</a>. Because they are both hydrogen-bond acceptors (the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)−</span>) and hydrogen-bond donors (the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>), they also participate in <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonding</a>. Together, the hydroxyl and carbonyl group form the functional group carboxyl. Carboxylic acids usually exist as dimers in nonpolar media due to their tendency to "self-associate". Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas bigger carboxylic acids have limited solubility due to the increasing hydrophobic nature of the alkyl chain. These longer chain acids tend to be soluble in less-polar solvents such as ethers and alcohols.<sup id="cite_ref-M&B_3-0" class="reference"><a href="#cite_note-M&B-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Aqueous sodium hydroxide and carboxylic acids, even hydrophobic ones, react to yield water-soluble sodium salts. For example, <a href="/wiki/Enanthic_acid" title="Enanthic acid">enanthic acid</a> has a low solubility in water (0.2 g/L), but its sodium salt is very soluble in water. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Solubility_in_different_environments.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Solubility_in_different_environments.jpg/500px-Solubility_in_different_environments.jpg" decoding="async" width="500" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/1e/Solubility_in_different_environments.jpg 1.5x" data-file-width="700" data-file-height="250" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Boiling_points">Boiling points</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=4" title="Edit section: Boiling points"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids tend to have higher boiling points than water, because of their greater surface areas and their tendency to form stabilized dimers through <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a>. For boiling to occur, either the dimer bonds must be broken or the entire dimer arrangement must be vaporized, increasing the <a href="/wiki/Enthalpy_of_vaporization" title="Enthalpy of vaporization">enthalpy of vaporization</a> requirements significantly. </p> <dl><dd><figure class="mw-default-size mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Carboxylic_acid_dimers.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Carboxylic_acid_dimers.png/220px-Carboxylic_acid_dimers.png" decoding="async" width="220" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Carboxylic_acid_dimers.png/330px-Carboxylic_acid_dimers.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Carboxylic_acid_dimers.png/440px-Carboxylic_acid_dimers.png 2x" data-file-width="1803" data-file-height="827" /></a><figcaption>Carboxylic acid <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimers</a></figcaption></figure></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=5" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids are <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acids</a> because they are proton (H<sup>+</sup>) donors. They are the most common type of <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a>. </p><p>Carboxylic acids are typically <a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">weak acids</a>, meaning that they only partially <a href="/wiki/Dissociation_(chemistry)" title="Dissociation (chemistry)">dissociate</a> into <a href="/wiki/Hydronium" title="Hydronium"><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></a> <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a> and <a href="/wiki/Carboxylate" title="Carboxylate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CO<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a> in neutral <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">aqueous</a> solution. For example, at room temperature, in a 1-<a href="/wiki/Molarity" class="mw-redirect" title="Molarity">molar</a> solution of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, only 0.001% of the acid are dissociated (i.e. 10<sup>−5</sup> moles out of 1 mol). Electron-withdrawing substituents, such as <a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">-CF<sub>3</sub> group</a>, give stronger acids (the p<i>K</i><sub>a</sub> of acetic acid is 4.76 whereas trifluoroacetic acid, with a <a href="/wiki/Trifluoromethyl_group" title="Trifluoromethyl group">trifluoromethyl substituent</a>, has a p<i>K</i><sub>a</sub> of 0.23). Electron-donating substituents give weaker acids (the p<i>K</i><sub>a</sub> of formic acid is 3.75 whereas acetic acid, with a <a href="/wiki/Methyl_group" title="Methyl group">methyl substituent</a>, has a p<i>K</i><sub>a</sub> of 4.76) </p> <table class="wikitable"> <tbody><tr> <th>Carboxylic acid<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> </th> <th><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> </th></tr> <tr> <td><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>3.75 </td></tr> <tr> <td><a href="/wiki/Chloroformic_acid" title="Chloroformic acid">Chloroformic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ClCO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>0.27<sup id="cite_ref-metabolites_5-0" class="reference"><a href="#cite_note-metabolites-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>4.76 </td></tr> <tr> <td><a href="/wiki/Glycine" title="Glycine">Glycine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>2.34 </td></tr> <tr> <td><a href="/wiki/Fluoroacetic_acid" title="Fluoroacetic acid">Fluoroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">FCH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>2.586 </td></tr> <tr> <td><a href="/wiki/Difluoroacetic_acid" title="Difluoroacetic acid">Difluoroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">F<sub class="template-chem2-sub">2</sub>CHCO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>1.33 </td></tr> <tr> <td><a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">Trifluoroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>0.23 </td></tr> <tr> <td><a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">Chloroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ClCH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>2.86 </td></tr> <tr> <td><a href="/wiki/Dichloroacetic_acid" title="Dichloroacetic acid">Dichloroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub>CHCO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>1.29 </td></tr> <tr> <td><a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">Trichloroacetic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CCl<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>0.65 </td></tr> <tr> <td><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>−CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>4.2 </td></tr> <tr> <td><a href="/wiki/2-Nitrobenzoic_acid" title="2-Nitrobenzoic acid">2-Nitrobenzoic acid</a> (<i>ortho</i>-<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">4</sub>(NO<sub class="template-chem2-sub">2</sub>)CO<sub class="template-chem2-sub">2</sub>H</span>)</td> <td>2.16 </td></tr> <tr> <td><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HO−C(=O)−C(=O)−OH</span>) (first dissociation) </td> <td>1.27 </td></tr> <tr> <td><a href="/wiki/Oxalic_acid#Acid-base_properties" title="Oxalic acid">Hydrogen oxalate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HO−C(=O)−CO<span class="template-chem2-su"><span>−</span><span>2</span></span></span>) (second dissociation of oxalic acid) </td> <td>4.14 </td></tr> </tbody></table> <p><a href="/wiki/Deprotonation" title="Deprotonation">Deprotonation</a> of carboxylic acids gives carboxylate anions; these are <a href="/wiki/Resonance_stabilized" class="mw-redirect" title="Resonance stabilized">resonance stabilized</a>, because the negative charge is delocalized over the two oxygen atoms, increasing the stability of the anion. Each of the carbon–oxygen bonds in the carboxylate anion has a partial double-bond character. The carbonyl carbon's partial positive charge is also weakened by the -<sup>1</sup>/<sub>2</sub> negative charges on the 2 oxygen atoms. </p> <div class="mw-heading mw-heading3"><h3 id="Odour">Odour</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=6" title="Edit section: Odour"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids often have strong sour odours. <a href="/wiki/Esters" class="mw-redirect" title="Esters">Esters</a> of carboxylic acids tend to have fruity, pleasant odours, and many are used in <a href="/wiki/Perfume" title="Perfume">perfume</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Characterization">Characterization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=7" title="Edit section: Characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids are readily identified as such by <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a>. They exhibit a sharp band associated with vibration of the C=O carbonyl bond (<i>ν</i><sub>C=O</sub>) between 1680 and 1725 cm<sup>−1</sup>. A characteristic <i>ν</i><sub>O–H</sub> band appears as a broad peak in the 2500 to 3000 cm<sup>−1</sup> region.<sup id="cite_ref-M&B_3-1" class="reference"><a href="#cite_note-M&B-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> By <sup>1</sup>H <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR</a> spectrometry, the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> hydrogen appears in the 10–13 ppm region, although it is often either broadened or not observed owing to exchange with traces of water. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_applications">Occurrence and applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=8" title="Edit section: Occurrence and applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many carboxylic acids are produced industrially on a large scale. They are also frequently found in nature. Esters of fatty acids are the main components of lipids and polyamides of <a href="/wiki/Amino_acid" title="Amino acid">aminocarboxylic acids</a> are the main components of <a href="/wiki/Protein" title="Protein">proteins</a>. </p><p>Carboxylic acids are used in the production of polymers, pharmaceuticals, solvents, and food additives. Industrially important carboxylic acids include <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> (component of vinegar, precursor to solvents and coatings), <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic and methacrylic acids</a> (precursors to polymers, adhesives), <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a> (polymers), <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a> (a flavor and preservative in food and beverages), <a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">ethylenediaminetetraacetic acid</a> (chelating agent), <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> (coatings), <a href="/wiki/Maleic_acid" title="Maleic acid">maleic acid</a> (polymers), <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> (food preservative), <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> (polymers). Important carboxylate salts are soaps. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=9" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial_routes">Industrial routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=10" title="Edit section: Industrial routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, industrial routes to carboxylic acids differ from those used on a smaller scale because they require specialized equipment. </p> <ul><li>Carbonylation of alcohols as illustrated by the <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a> for the production of acetic acid. Formic acid is prepared by a different carbonylation pathway, also starting from methanol.</li> <li>Oxidation of <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> with air using cobalt and manganese catalysts. The required aldehydes are readily obtained from alkenes by <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a>.</li> <li>Oxidation of hydrocarbons using air. For simple alkanes, this method is inexpensive but not selective enough to be useful. Allylic and benzylic compounds undergo more selective oxidations. Alkyl groups on a benzene ring are oxidized to the carboxylic acid, regardless of its chain length. <a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a> from <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> from <i>para</i>-<a href="/wiki/Xylene" title="Xylene">xylene</a>, and <a href="/wiki/Phthalic_acid" title="Phthalic acid">phthalic acid</a> from <i>ortho</i>-<a href="/wiki/Xylene" title="Xylene">xylene</a> are illustrative large-scale conversions. <a href="/wiki/Acrylic_acid" title="Acrylic acid">Acrylic acid</a> is generated from <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>.<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></li> <li>Oxidation of ethene using <a href="/wiki/Silicotungstic_acid" title="Silicotungstic acid">silicotungstic acid</a> catalyst.</li> <li>Base-catalyzed dehydrogenation of alcohols.</li> <li>Carbonylation coupled to the addition of water. This method is effective and versatile for alkenes that generate secondary and tertiary <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>, e.g. <a href="/wiki/Isobutylene" title="Isobutylene">isobutylene</a> to <a href="/wiki/Pivalic_acid" title="Pivalic acid">pivalic acid</a>. In the <a href="/wiki/Koch_reaction" title="Koch reaction">Koch reaction</a>, the addition of water and carbon monoxide to <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a> or <a href="/wiki/Alkynes" class="mw-redirect" title="Alkynes">alkynes</a> is catalyzed by strong acids. Hydrocarboxylations involve the simultaneous addition of water and <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a>. Such reactions are sometimes called "<a href="/wiki/Walter_Reppe" title="Walter Reppe">Reppe chemistry</a>."</li></ul> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Acetylene" title="Acetylene">HC≡CH</a> + CO + H<sub class="template-chem2-sub">2</sub>O → <a href="/wiki/Acrylic_acid" title="Acrylic acid">CH<sub class="template-chem2-sub">2</sub>=CH−CO<sub class="template-chem2-sub">2</sub>H</a></span></dd></dl> <ul><li>Hydrolysis of <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a> obtained from plant or animal oils. These methods of synthesizing some long-chain carboxylic acids are related to <a href="/wiki/Soap_making" class="mw-redirect" title="Soap making">soap making</a>.</li> <li><a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">Fermentation</a> of ethanol. This method is used in the production of <a href="/wiki/Vinegar" title="Vinegar">vinegar</a>.</li> <li>The <a href="/wiki/Kolbe%E2%80%93Schmitt_reaction" title="Kolbe–Schmitt reaction">Kolbe–Schmitt reaction</a> provides a route to <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a>, precursor to <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Laboratory_methods">Laboratory methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=11" title="Edit section: Laboratory methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Preparative methods for small scale reactions for research or for production of fine chemicals often employ expensive consumable reagents. </p> <ul><li><a href="/wiki/Oxidation_of_primary_alcohols_to_carboxylic_acids" class="mw-redirect" title="Oxidation of primary alcohols to carboxylic acids">Oxidation of primary alcohols</a> or <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> with strong <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidants</a> such as <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a>, <a href="/wiki/Jones_reagent" class="mw-redirect" title="Jones reagent">Jones reagent</a>, <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a>, or <a href="/wiki/Sodium_chlorite" title="Sodium chlorite">sodium chlorite</a>. The method is more suitable for laboratory conditions than the industrial use of air, which is "greener" because it yields less inorganic side products such as chromium or manganese oxides.<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. (September 2019)">citation needed</span></a></i>]</sup></li> <li>Oxidative cleavage of <a href="/wiki/Olefin" class="mw-redirect" title="Olefin">olefins</a> by <a href="/wiki/Ozonolysis" title="Ozonolysis">ozonolysis</a>, <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a>, or <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a>.</li> <li>Hydrolysis of <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>, <a href="/wiki/Ester" title="Ester">esters</a>, or <a href="/wiki/Amide" title="Amide">amides</a>, usually with acid- or base-catalysis.</li> <li>Carbonation of a <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a> and <a href="/wiki/Organolithium" class="mw-redirect" title="Organolithium">organolithium</a> reagents:</li></ul> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RLi + <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub class="template-chem2-sub">2</sub></a> → RCO<span class="template-chem2-su"><span>−</span><span>2</span></span>Li<sup class="template-chem2-sup">+</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<span class="template-chem2-su"><span>−</span><span>2</span></span>Li<sup class="template-chem2-sup">+</sup> + <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a> → RCO<sub class="template-chem2-sub">2</sub>H + <a href="/wiki/Lithium_chloride" title="Lithium chloride">LiCl</a></span></dd></dl> <ul><li><a href="/wiki/Halogenation" title="Halogenation">Halogenation</a> followed by hydrolysis of <a href="/wiki/Methyl_ketone" class="mw-redirect" title="Methyl ketone">methyl ketones</a> in the <a href="/wiki/Haloform_reaction" title="Haloform reaction">haloform reaction</a></li> <li>Base-catalyzed cleavage of non-enolizable ketones, especially <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> ketones:<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li></ul> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−<a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Ar</a> + H<sub class="template-chem2-sub">2</sub>O → R−CO<sub class="template-chem2-sub">2</sub>H + ArH</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Less-common_reactions">Less-common reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=12" title="Edit section: Less-common reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many reactions produce carboxylic acids but are used only in specific cases or are mainly of academic interest. </p> <ul><li>Disproportionation of an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> in the <a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a></li> <li>Rearrangement of diketones in the <a href="/wiki/Benzilic_acid_rearrangement" title="Benzilic acid rearrangement">benzilic acid rearrangement</a></li> <li>Involving the generation of benzoic acids are the <a href="/wiki/Von_Richter_reaction" title="Von Richter reaction">von Richter reaction</a> from nitrobenzenes and the <a href="/wiki/Kolbe%E2%80%93Schmitt_reaction" title="Kolbe–Schmitt reaction">Kolbe–Schmitt reaction</a> from <a href="/wiki/Phenol" title="Phenol">phenols</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=13" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Carboxylic_Acid_Sunshine_Diagram1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/Carboxylic_Acid_Sunshine_Diagram1.svg/400px-Carboxylic_Acid_Sunshine_Diagram1.svg.png" decoding="async" width="400" height="251" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/Carboxylic_Acid_Sunshine_Diagram1.svg/600px-Carboxylic_Acid_Sunshine_Diagram1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/10/Carboxylic_Acid_Sunshine_Diagram1.svg/800px-Carboxylic_Acid_Sunshine_Diagram1.svg.png 2x" data-file-width="467" data-file-height="293" /></a><figcaption>Carboxylic acid <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Acid-base_reactions">Acid-base reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=14" title="Edit section: Acid-base reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids react with <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a> to form carboxylate salts, in which the <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> of the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (–OH) group is replaced with a metal <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a>. For example, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> found in <a href="/wiki/Vinegar" title="Vinegar">vinegar</a> reacts with <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> (baking soda) to form <a href="/wiki/Sodium_acetate" title="Sodium acetate">sodium acetate</a>, <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, and water: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH + NaHCO<sub class="template-chem2-sub">3</sub> → CH<sub class="template-chem2-sub">3</sub>COO<sup class="template-chem2-sup">−</sup>Na<sup class="template-chem2-sup">+</sup> + CO<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_esters,_amides,_anhydrides"><span id="Conversion_to_esters.2C_amides.2C_anhydrides"></span>Conversion to esters, amides, anhydrides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=15" title="Edit section: Conversion to esters, amides, anhydrides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Widely practiced reactions convert carboxylic acids into <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a>, <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a>, <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate salts</a>, <a href="/wiki/Acid_chlorides" class="mw-redirect" title="Acid chlorides">acid chlorides</a>, and <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>. Their conversion to <a href="/wiki/Ester" title="Ester">esters</a> is widely used, e.g. in the production of <a href="/wiki/Polyester" title="Polyester">polyesters</a>. Likewise, carboxylic acids are converted into <a href="/wiki/Amide" title="Amide">amides</a>, but this conversion typically does not occur by direct reaction of the carboxylic acid and the amine. Instead esters are typical precursors to amides. The conversion of <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> into <a href="/wiki/Peptide" title="Peptide">peptides</a> is a significant biochemical process that requires <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>. </p><p>Converting a carboxylic acid to an amide is possible, but not straightforward. Instead of acting as a nucleophile, an amine will react as a base in the presence of a carboxylic acid to give the ammonium <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a> salt. Heating the salt to above 100 °C will drive off water and lead to the formation of the amide. This method of synthesizing amides is industrially important, and has laboratory applications as well.<sup id="cite_ref-wade2_9-0" class="reference"><a href="#cite_note-wade2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In the presence of a strong acid catalyst, carboxylic acids can <a href="/wiki/Condensation_reaction" title="Condensation reaction">condense</a> to form acid anhydrides. The condensation produces water, however, which can hydrolyze the anhydride back to the starting carboxylic acids. Thus, the formation of the anhydride via condensation is an equilibrium process. </p><p>Under acid-catalyzed conditions, carboxylic acids will react with alcohols to form <a href="/wiki/Ester" title="Ester">esters</a> via the <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a> reaction, which is also an equilibrium process. Alternatively, <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> can be used to convert an acid to an ester. While esterification reactions with diazomethane often give quantitative yields, diazomethane is only useful for forming methyl esters.<sup id="cite_ref-wade2_9-1" class="reference"><a href="#cite_note-wade2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=16" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like <a href="/wiki/Ester" title="Ester">esters</a>, most carboxylic acids can be <a href="/wiki/Carboxylic_acid_reduction" class="mw-redirect" title="Carboxylic acid reduction">reduced</a> to alcohols by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, or using hydride transferring agents such as <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>. Strong alkyl transferring agents, such as <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium</a> compounds but not <a href="/wiki/Grignard_reagents" class="mw-redirect" title="Grignard reagents">Grignard reagents</a>, will reduce carboxylic acids to ketones along with transfer of the alkyl group. </p><p>The <a href="/wiki/Vilsmaier_reagent" class="mw-redirect" title="Vilsmaier reagent">Vilsmaier reagent</a> (<i>N</i>,<i>N</i>-Dimethyl(chloromethylene)ammonium chloride; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[ClHC=N<sup class="template-chem2-sup">+</sup>(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>]Cl<sup class="template-chem2-sup">−</sup></span>) is a highly chemoselective agent for carboxylic acid reduction. It selectively activates the carboxylic acid to give the carboxymethyleneammonium salt, which can be reduced by a mild reductant like lithium tris(<i>t</i>-butoxy)aluminum hydride to afford an aldehyde in a one pot procedure. This procedure is known to tolerate reactive carbonyl functionalities such as ketone as well as moderately reactive ester, olefin, nitrile, and halide moieties.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p><span class="anchor" id="Barbier-Wieland_degradation"></span> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_acyl_halides">Conversion to acyl halides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=17" title="Edit section: Conversion to acyl halides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The hydroxyl group on carboxylic acids may be replaced with a chlorine atom using <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a> to give <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a>. In nature, carboxylic acids are converted to <a href="/wiki/Thioester" title="Thioester">thioesters</a>. <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">Thionyl chloride</a> can be used to convert carboxylic acids to their corresponding acyl chlorides. First, carboxylic acid <b>1</b> attacks thionyl chloride, and chloride ion leaves. The resulting <a href="/wiki/Oxonium_ion" title="Oxonium ion">oxonium ion</a> <b>2</b> is activated towards nucleophilic attack and has a good leaving group, setting it apart from a normal carboxylic acid. In the next step, <b>2</b> is attacked by chloride ion to give tetrahedral intermediate <b>3</b>, a chlorosulfite. The tetrahedral intermediate collapses with the loss of <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a> and chloride ion, giving protonated acyl chloride <b>4</b>. Chloride ion can remove the proton on the carbonyl group, giving the acyl chloride <b>5</b> with a loss of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a>. </p><p><span typeof="mw:File"><a href="/wiki/File:Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png" class="mw-file-description" title="Mechanism for the reaction of a carboxylic acid with thionyl chloride to give an acid chloride"><img alt="Mechanism for the reaction of a carboxylic acid with thionyl chloride to give an acid chloride" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png/700px-Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png" decoding="async" width="700" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png/1050px-Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png/1400px-Mechanism_of_the_Reaction_of_a_Carboxylic_Acid_and_Thionyl_Chloride.png 2x" data-file-width="2574" data-file-height="510" /></a></span> </p><p><a href="/wiki/Phosphorus(III)_chloride" class="mw-redirect" title="Phosphorus(III) chloride">Phosphorus(III) chloride</a> (PCl<sub>3</sub>) and <a href="/wiki/Phosphorus(V)_chloride" class="mw-redirect" title="Phosphorus(V) chloride">phosphorus(V) chloride</a> (PCl<sub>5</sub>) will also convert carboxylic acids to acid chlorides, by a similar mechanism. One equivalent of PCl<sub>3</sub> can react with three equivalents of acid, producing one equivalent of H<sub>3</sub>PO<sub>3</sub>, or <a href="/wiki/Phosphorus_acid" class="mw-redirect" title="Phosphorus acid">phosphorus acid</a>, in addition to the desired acid chloride. PCl<sub>5</sub> reacts with carboxylic acids in a 1:1 ratio, and produces <a href="/wiki/Phosphorus(V)_oxychloride" class="mw-redirect" title="Phosphorus(V) oxychloride">phosphorus(V) oxychloride</a> (POCl<sub>3</sub>) and hydrogen chloride (HCl) as byproducts. </p> <div class="mw-heading mw-heading3"><h3 id="Reactions_with_carbanion_equivalents">Reactions with carbanion equivalents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=18" title="Edit section: Reactions with carbanion equivalents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids react with Grignard reagents and organolithiums to form ketones. The first equivalent of nucleophile acts as a base and deprotonates the acid. A second equivalent will attack the carbonyl group to create a <a href="/wiki/Geminal" title="Geminal">geminal</a> alkoxide dianion, which is protonated upon workup to give the hydrate of a ketone. Because most ketone hydrates are unstable relative to their corresponding ketones, the equilibrium between the two is shifted heavily in favor of the ketone. For example, the equilibrium constant for the formation of <a href="/wiki/Acetone" title="Acetone">acetone</a> hydrate from acetone is only 0.002. The carboxylic group is the most acidic in organic compounds.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Specialized_reactions">Specialized reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=19" title="Edit section: Specialized reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>As with all carbonyl compounds, the protons on the <a href="/wiki/Alpha-carbon" class="mw-redirect" title="Alpha-carbon">α-carbon</a> are labile due to <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">keto–enol tautomerization</a>. Thus, the α-carbon is easily halogenated in the <a href="/wiki/Hell%E2%80%93Volhard%E2%80%93Zelinsky_halogenation" title="Hell–Volhard–Zelinsky halogenation">Hell–Volhard–Zelinsky halogenation</a>.</li> <li>The <a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a> converts carboxylic acids to <a href="/wiki/Amine" title="Amine">amines</a>.</li> <li>Carboxylic acids are decarboxylated in the <a href="/wiki/Hunsdiecker_reaction" title="Hunsdiecker reaction">Hunsdiecker reaction</a>.</li> <li>The <a href="/wiki/Dakin%E2%80%93West_reaction" title="Dakin–West reaction">Dakin–West reaction</a> converts an amino acid to the corresponding amino ketone.</li> <li>In the <a href="/wiki/Barbier%E2%80%93Wieland_degradation" title="Barbier–Wieland degradation">Barbier–Wieland degradation</a>, a carboxylic acid on an aliphatic chain having a simple <a href="/wiki/Methylene_bridge" title="Methylene bridge">methylene bridge</a> at the alpha position can have the chain shortened by one carbon. The inverse procedure is the <a href="/wiki/Arndt%E2%80%93Eistert_synthesis" class="mw-redirect" title="Arndt–Eistert synthesis">Arndt–Eistert synthesis</a>, where an acid is converted into acyl halide, which is then reacted with <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> to give one additional methylene in the aliphatic chain.</li> <li>Many acids undergo <a href="/wiki/Oxidative_decarboxylation" title="Oxidative decarboxylation">oxidative decarboxylation</a>. <a href="/wiki/Enzyme" title="Enzyme">Enzymes</a> that catalyze these reactions are known as <a href="/wiki/Carboxylase" class="mw-redirect" title="Carboxylase">carboxylases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 6.4.1) and <a href="/wiki/Decarboxylase" class="mw-redirect" title="Decarboxylase">decarboxylases</a> (EC 4.1.1).</li> <li>Carboxylic acids are reduced to <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> via the <a href="/wiki/Ester" title="Ester">ester</a> and <a href="/wiki/Diisobutylaluminium_hydride" title="Diisobutylaluminium hydride">DIBAL</a>, via the acid chloride in the <a href="/wiki/Rosenmund_reduction" title="Rosenmund reduction">Rosenmund reduction</a> and via the thioester in the <a href="/wiki/Fukuyama_reduction" title="Fukuyama reduction">Fukuyama reduction</a>.</li> <li>In <a href="/wiki/Ketonic_decarboxylation" title="Ketonic decarboxylation">ketonic decarboxylation</a> carboxylic acids are converted to ketones.</li> <li>Organolithium reagents (>2 equiv) react with carboxylic acids to give a dilithium 1,1-diolate, a stable <a href="/wiki/Tetrahedral_intermediate" class="mw-redirect" title="Tetrahedral intermediate">tetrahedral intermediate</a> which decomposes to give a ketone upon acidic workup.</li> <li>The <a href="/wiki/Kolbe_electrolysis" title="Kolbe electrolysis">Kolbe electrolysis</a> is an electrolytic, decarboxylative dimerization reaction. It gets rid of the carboxyl groups of two acid molecules, and joins the remaining fragments together.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Carboxyl_radical">Carboxyl radical</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=20" title="Edit section: Carboxyl radical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carboxyl <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">radical</a>, •COOH, only exists briefly.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">acid dissociation constant</a> of •COOH has been measured using <a href="/wiki/Electron_paramagnetic_resonance" title="Electron paramagnetic resonance">electron paramagnetic resonance</a> spectroscopy.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The carboxyl group tends to dimerise to form <a href="/wiki/Oxalic_acid" title="Oxalic acid">oxalic acid</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=21" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Acid_anhydride" title="Acid anhydride">Acid anhydride</a></li> <li><a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">Acid chloride</a></li> <li><a href="/wiki/Amide" title="Amide">Amide</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a></li> <li><a href="/wiki/Ester" title="Ester">Ester</a></li> <li><a href="/wiki/List_of_carboxylic_acids" title="List of carboxylic acids">List of carboxylic acids</a></li> <li><a href="/wiki/Dicarboxylic_acid" title="Dicarboxylic acid">Dicarboxylic acid</a></li> <li><a href="/wiki/Pseudoacid" title="Pseudoacid">Pseudoacid</a></li> <li><a href="/wiki/Thiocarboxy" class="mw-redirect" title="Thiocarboxy">Thiocarboxy</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a> (CO<sub>2</sub>)</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboxylic_acid&action=edit&section=22" 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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/C00852.html">carboxylic acids</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C00852">10.1351/goldbook.C00852</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_24.htm">Recommendations 1979</a>. Organic Chemistry IUPAC Nomenclature. Rules C-4 Carboxylic Acids and Their Derivatives.</span> </li> <li id="cite_note-M&B-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-M&B_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-M&B_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMorrisonBoyd1992" class="citation book cs1">Morrison, R.T.; Boyd, R.N. (1992). <i>Organic Chemistry</i> (6th ed.). Prentice Hall. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-13-643669-2" title="Special:BookSources/0-13-643669-2"><bdi>0-13-643669-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.edition=6th&rft.pub=Prentice+Hall&rft.date=1992&rft.isbn=0-13-643669-2&rft.aulast=Morrison&rft.aufirst=R.T.&rft.au=Boyd%2C+R.N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes2011" class="citation book cs1">Haynes, William M., ed. (2011). <a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics"><i>CRC Handbook of Chemistry and Physics</i></a> (92nd ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. pp. 5–94 to 5–98. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1439855119" title="Special:BookSources/978-1439855119"><bdi>978-1439855119</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.pages=5-94+to+5-98&rft.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=978-1439855119&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-metabolites-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-metabolites_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://hmdb.ca/metabolites/HMDB0250109">"Chlorocarbonic acid"</a>. <i>Human Metabolome Database</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Human+Metabolome+Database&rft.atitle=Chlorocarbonic+acid&rft_id=https%3A%2F%2Fhmdb.ca%2Fmetabolites%2FHMDB0250109&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith" class="citation web cs1">Smith, Brian. <a rel="nofollow" class="external text" href="https://www.spectroscopyonline.com/view/co-bond-part-viii-review">"The C=O Bond, Part VIII: Review"</a>. <i>Spectroscopy</i><span class="reference-accessdate">. Retrieved <span class="nowrap">12 February</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=Spectroscopy&rft.atitle=The+C%3DO+Bond%2C+Part+VIII%3A+Review&rft.aulast=Smith&rft.aufirst=Brian&rft_id=https%3A%2F%2Fwww.spectroscopyonline.com%2Fview%2Fco-bond-part-viii-review&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" 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="CITEREFRiemenschneider2002" class="citation book cs1">Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a05_235">10.1002/14356007.a05_235</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Carboxylic+Acids%2C+Aliphatic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2002&rft_id=info%3Adoi%2F10.1002%2F14356007.a05_235&rft.isbn=3527306730&rft.aulast=Riemenschneider&rft.aufirst=Wilhelm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span>.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerry_C._Reeves1977" class="citation journal cs1">Perry C. Reeves (1977). "Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid". <i>Org. Synth</i>. <b>56</b>: 28. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.056.0028">10.15227/orgsyn.056.0028</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Carboxylation+of+Aromatic+Compounds%3A+Ferrocenecarboxylic+Acid&rft.volume=56&rft.pages=28&rft.date=1977&rft_id=info%3Adoi%2F10.15227%2Forgsyn.056.0028&rft.au=Perry+C.+Reeves&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-wade2-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-wade2_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-wade2_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Wade 2010, pp. 964–965.</span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFujisawaSato" class="citation journal cs1">Fujisawa, Tamotsu; Sato, Toshio. <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV8P0498">"Reduction of carboxylic acids to aldehydes: 6-Ooxdecanal"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>66</b>: 121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.066.0121">10.15227/orgsyn.066.0121</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Reduction+of+carboxylic+acids+to+aldehydes%3A+6-Ooxdecanal&rft.volume=66&rft.pages=121&rft_id=info%3Adoi%2F10.15227%2Forgsyn.066.0121&rft.aulast=Fujisawa&rft.aufirst=Tamotsu&rft.au=Sato%2C+Toshio&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3DCV8P0498&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 8, p. 498</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=498&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span>.</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">Wade 2010, p. 838.</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMilligan,_D._E.Jacox,_M._E.1971" class="citation journal cs1">Milligan, D. E.; Jacox, M. E. (1971). "Infrared Spectrum and Structure of Intermediates in Reaction of OH with CO". <i>Journal of Chemical Physics</i>. <b>54</b> (3): 927–942. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1971JChPh..54..927M">1971JChPh..54..927M</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F1.1675022">10.1063/1.1675022</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Physics&rft.atitle=Infrared+Spectrum+and+Structure+of+Intermediates+in+Reaction+of+OH+with+CO&rft.volume=54&rft.issue=3&rft.pages=927-942&rft.date=1971&rft_id=info%3Adoi%2F10.1063%2F1.1675022&rft_id=info%3Abibcode%2F1971JChPh..54..927M&rft.au=Milligan%2C+D.+E.&rft.au=Jacox%2C+M.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">The value is p<i>K</i><sub>a</sub> = −0.2 ± 0.1. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJeevarajanCarmichaelFessenden1990" class="citation journal cs1">Jeevarajan, A. S.; Carmichael, I.; Fessenden, R. W. (1990). "ESR Measurement of the p<i>K</i><sub>a</sub> of Carboxyl Radical and Ab Initio Calculation of the Carbon-13 Hyperfine Constant". <i>Journal of Physical Chemistry</i>. <b>94</b> (4): 1372–1376. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fj100367a033">10.1021/j100367a033</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Physical+Chemistry&rft.atitle=ESR+Measurement+of+the+pK%3Csub%3Ea%3C%2Fsub%3E+of+Carboxyl+Radical+and+Ab+Initio+Calculation+of+the+Carbon-13+Hyperfine+Constant&rft.volume=94&rft.issue=4&rft.pages=1372-1376&rft.date=1990&rft_id=info%3Adoi%2F10.1021%2Fj100367a033&rft.aulast=Jeevarajan&rft.aufirst=A.+S.&rft.au=Carmichael%2C+I.&rft.au=Fessenden%2C+R.+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboxylic+acid" class="Z3988"></span></span> </li> </ol></div></div> <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=Carboxylic_acid&action=edit&section=23" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/carboxyl" class="extiw" title="wiktionary:carboxyl">carboxyl</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li>Carboxylic acids pH and titration <a rel="nofollow" class="external text" href="http://www2.iq.usp.br/docente/gutz/Curtipot_.html">– freeware for calculations, data analysis, simulation, and distribution diagram generation</a></li> <li><a rel="nofollow" class="external text" href="https://agrocode.com/en/glosario_terminos/polyhydroxycarboxylic-acids/">PHC.</a></li></ul> <div class="navbox-styles"><style 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aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Topics_in_organic_reactions" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Organic_reactions" title="Template:Organic reactions"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organic_reactions" title="Template talk:Organic reactions"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organic_reactions" title="Special:EditPage/Template:Organic reactions"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Topics_in_organic_reactions" style="font-size:114%;margin:0 4em">Topics in <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reaction</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Polymerization" title="Polymerization">Polymerization</a></li> <li><a href="/wiki/Category:Reagents_for_organic_chemistry" title="Category:Reagents for organic chemistry">Reagents</a></li> <li><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement reaction</a></li> <li><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Redox reaction</a></li> <li><a href="/wiki/Regioselectivity" title="Regioselectivity">Regioselectivity</a></li> <li><a href="/wiki/Stereoselectivity" title="Stereoselectivity">Stereoselectivity</a></li> <li><a href="/wiki/Stereospecificity" title="Stereospecificity">Stereospecificity</a></li> <li><a href="/wiki/Substitution_reaction" title="Substitution reaction">Substitution reaction</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A_value" title="A value">A value</a></li> <li><a href="/wiki/Alpha_effect" title="Alpha effect">Alpha effect</a></li> <li><a href="/wiki/Annulene" title="Annulene">Annulene</a></li> <li><a href="/wiki/Anomeric_effect" title="Anomeric effect">Anomeric effect</a></li> <li><a href="/wiki/Antiaromaticity" title="Antiaromaticity">Antiaromaticity</a></li> <li><a href="/wiki/Aromatic_ring_current" title="Aromatic ring current">Aromatic ring current</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/Baker%E2%80%93Nathan_effect" title="Baker–Nathan effect">Baker–Nathan effect</a></li> <li><a href="/wiki/Baldwin%27s_rules" title="Baldwin's rules">Baldwin's rules</a></li> <li><a href="/wiki/Bema_Hapothle" title="Bema Hapothle">Bema Hapothle</a></li> <li><a href="/wiki/Beta-silicon_effect" class="mw-redirect" title="Beta-silicon effect">Beta-silicon effect</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">Bicycloaromaticity</a></li> <li><a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a></li> <li><a href="/wiki/B%C3%BCrgi%E2%80%93Dunitz_angle" title="Bürgi–Dunitz angle">Bürgi–Dunitz angle</a></li> <li><a href="/wiki/Catalytic_resonance_theory" title="Catalytic resonance theory">Catalytic resonance theory</a></li> <li><a href="/wiki/Charge_remote_fragmentation" class="mw-redirect" title="Charge remote fragmentation">Charge remote fragmentation</a></li> <li><a href="/wiki/Charge-transfer_complex" title="Charge-transfer complex">Charge-transfer complex</a></li> <li><a href="/wiki/Clar%27s_rule" title="Clar's rule">Clar's rule</a></li> <li><a href="/wiki/Conformational_isomerism" title="Conformational isomerism">Conformational isomerism</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugated system</a></li> <li><a href="/wiki/Conrotatory_and_disrotatory" title="Conrotatory and disrotatory">Conrotatory and disrotatory</a></li> <li><a href="/wiki/Curtin%E2%80%93Hammett_principle" title="Curtin–Hammett principle">Curtin–Hammett principle</a></li> <li><a href="/wiki/Dynamic_binding_(chemistry)" title="Dynamic binding (chemistry)">Dynamic binding (chemistry)</a></li> <li><a href="/wiki/Edwards_equation" title="Edwards equation">Edwards equation</a></li> <li><a href="/wiki/Effective_molarity" title="Effective molarity">Effective molarity</a></li> <li><a href="/wiki/Electromeric_effect" title="Electromeric effect">Electromeric effect</a></li> <li><a href="/wiki/Electron-rich" title="Electron-rich">Electron-rich</a></li> <li><a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">Electron-withdrawing group</a></li> <li><a href="/wiki/Electronic_effect" title="Electronic effect">Electronic effect</a></li> <li><a href="/wiki/Electrophile" title="Electrophile">Electrophile</a></li> <li><a href="/wiki/Evelyn_effect" title="Evelyn effect">Evelyn effect</a></li> <li><a href="/wiki/Flippin%E2%80%93Lodge_angle" title="Flippin–Lodge angle">Flippin–Lodge angle</a></li> <li><a href="/wiki/Free-energy_relationship" title="Free-energy relationship">Free-energy relationship</a></li> <li><a href="/wiki/Grunwald%E2%80%93Winstein_equation" title="Grunwald–Winstein equation">Grunwald–Winstein equation</a></li> <li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li> <li><a href="/wiki/Hammett_equation" title="Hammett equation">Hammett equation</a></li> <li><a href="/wiki/George_S._Hammond" title="George S. Hammond">George S. Hammond</a></li> <li><a href="/wiki/Hammond%27s_postulate" title="Hammond's postulate">Hammond's postulate</a></li> <li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">Homoaromaticity</a></li> <li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Inductive_effect" title="Inductive effect">Inductive effect</a></li> <li><a href="/wiki/Kinetic_isotope_effect" title="Kinetic isotope effect">Kinetic isotope effect</a></li> <li><a href="/wiki/LFER_solvent_coefficients_(data_page)" title="LFER solvent coefficients (data page)">LFER solvent coefficients (data page)</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius aromaticity</a></li> <li><a href="/wiki/M%C3%B6bius%E2%80%93H%C3%BCckel_concept" title="Möbius–Hückel concept">Möbius–Hückel concept</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li> <li><a href="/wiki/Negative_hyperconjugation" title="Negative hyperconjugation">Negative hyperconjugation</a></li> <li><a href="/wiki/Neighbouring_group_participation" title="Neighbouring group participation">Neighbouring group participation</a></li> <li><a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-Norbornyl cation</a></li> <li><a href="/wiki/Nucleophile" title="Nucleophile">Nucleophile</a></li> <li><a href="/wiki/Kennedy_J._P._Orton" title="Kennedy J. P. Orton">Kennedy J. P. Orton</a></li> <li><a href="/wiki/Passive_binding" title="Passive binding">Passive binding</a></li> <li><a href="/wiki/Phosphaethynolate" title="Phosphaethynolate">Phosphaethynolate</a></li> <li><a href="/wiki/Polar_effect" class="mw-redirect" title="Polar effect">Polar effect</a></li> <li><a href="/wiki/Polyfluorene" title="Polyfluorene">Polyfluorene</a></li> <li><a href="/wiki/Ring_strain" title="Ring strain">Ring strain</a></li> <li><a href="/wiki/%CE%A3-aromaticity" class="mw-redirect" title="Σ-aromaticity">Σ-aromaticity</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">Spherical aromaticity</a></li> <li><a href="/wiki/Spiroaromaticity" class="mw-redirect" title="Spiroaromaticity">Spiroaromaticity</a></li> <li><a href="/wiki/Steric_effects" title="Steric effects">Steric effects</a></li> <li><a href="/wiki/Superaromaticity" class="mw-redirect" title="Superaromaticity">Superaromaticity</a></li> <li><a href="/wiki/Swain%E2%80%93Lupton_equation" title="Swain–Lupton equation">Swain–Lupton equation</a></li> <li><a href="/wiki/Taft_equation" title="Taft equation">Taft equation</a></li> <li><a href="/wiki/Thorpe%E2%80%93Ingold_effect" title="Thorpe–Ingold effect">Thorpe–Ingold effect</a></li> <li><a href="/wiki/Vinylogy" title="Vinylogy">Vinylogy</a></li> <li><a href="/wiki/Walsh_diagram" title="Walsh diagram">Walsh diagram</a></li> <li><a href="/wiki/Woodward%E2%80%93Hoffmann_rules" title="Woodward–Hoffmann rules">Woodward–Hoffmann rules</a></li> <li><a href="/wiki/Woodward%27s_rules" title="Woodward's rules">Woodward's rules</a></li> <li><a href="/wiki/Y-aromaticity" class="mw-redirect" title="Y-aromaticity">Y-aromaticity</a></li> <li><a href="/wiki/Yukawa%E2%80%93Tsuno_equation" title="Yukawa–Tsuno equation">Yukawa–Tsuno equation</a></li> <li><a href="/wiki/Zaitsev%27s_rule" class="mw-redirect" title="Zaitsev's rule">Zaitsev's rule</a></li> <li><a href="/wiki/%CE%A3-bishomoaromaticity" class="mw-redirect" title="Σ-bishomoaromaticity">Σ-bishomoaromaticity</a></li></ul> </div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="List_of_organic_reactions" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_organic_reactions" title="List of organic reactions">List of organic reactions</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-carbon <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetoacetic_ester_synthesis" title="Acetoacetic ester synthesis">Acetoacetic ester synthesis</a></li> <li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Aldol_condensation" title="Aldol condensation">Aldol condensation</a></li> <li><a href="/wiki/Aldol_reaction" title="Aldol reaction">Aldol reaction</a></li> <li><a href="/wiki/Alkane_metathesis" title="Alkane metathesis">Alkane metathesis</a></li> <li><a href="/wiki/Alkyne_metathesis" title="Alkyne metathesis">Alkyne metathesis</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a></li> <li><a href="/wiki/Barbier_reaction" title="Barbier reaction">Barbier reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Baylis%E2%80%93Hillman_reaction" title="Baylis–Hillman reaction">Baylis–Hillman reaction</a></li> <li><a href="/wiki/Benary_reaction" title="Benary reaction">Benary reaction</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bingel_reaction" title="Bingel reaction">Bingel reaction</a></li> <li><a href="/wiki/Blaise_ketone_synthesis" title="Blaise ketone synthesis">Blaise ketone synthesis</a></li> <li><a href="/wiki/Blaise_reaction" title="Blaise reaction">Blaise reaction</a></li> <li><a href="/wiki/Blanc_chloromethylation" title="Blanc chloromethylation">Blanc chloromethylation</a></li> <li><a href="/wiki/Bodroux%E2%80%93Chichibabin_aldehyde_synthesis" title="Bodroux–Chichibabin aldehyde synthesis">Bodroux–Chichibabin aldehyde synthesis</a></li> <li><a href="/wiki/Bouveault_aldehyde_synthesis" title="Bouveault aldehyde synthesis">Bouveault aldehyde synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Cadiot%E2%80%93Chodkiewicz_coupling" title="Cadiot–Chodkiewicz coupling">Cadiot–Chodkiewicz coupling</a></li> <li><a href="/wiki/Carbonyl_allylation" title="Carbonyl allylation">Carbonyl allylation</a></li> <li><a href="/wiki/Carbonyl_olefin_metathesis" title="Carbonyl olefin metathesis">Carbonyl olefin metathesis</a></li> <li><a href="/wiki/Castro%E2%80%93Stephens_coupling" title="Castro–Stephens coupling">Castro–Stephens coupling</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Chan%E2%80%93Lam_coupling" title="Chan–Lam coupling">Chan–Lam coupling</a></li> <li><a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Claisen-Schmidt_condensation" class="mw-redirect" title="Claisen-Schmidt condensation">Claisen-Schmidt condensation</a></li> <li><a href="/wiki/Combes_quinoline_synthesis" title="Combes quinoline synthesis">Combes quinoline synthesis</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Corey%E2%80%93House_synthesis" title="Corey–House synthesis">Corey–House synthesis</a></li> <li><a href="/wiki/Coupling_reaction" title="Coupling reaction">Coupling reaction</a></li> <li><a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">Cross-coupling reaction</a></li> <li><a href="/wiki/Cross_dehydrogenative_coupling" title="Cross dehydrogenative coupling">Cross dehydrogenative coupling</a></li> <li><a href="/wiki/Cross-coupling_partner" title="Cross-coupling partner">Cross-coupling partner</a></li> <li><a href="/wiki/Dakin%E2%80%93West_reaction" title="Dakin–West reaction">Dakin–West reaction</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Doebner_reaction" title="Doebner reaction">Doebner reaction</a></li> <li><a href="/wiki/Wulff%E2%80%93D%C3%B6tz_reaction" title="Wulff–Dötz reaction">Wulff–Dötz reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Ethenolysis" title="Ethenolysis">Ethenolysis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a></li> <li><a href="/wiki/Fujimoto%E2%80%93Belleau_reaction" title="Fujimoto–Belleau reaction">Fujimoto–Belleau reaction</a></li> <li><a href="/wiki/Fujiwara%E2%80%93Moritani_reaction" title="Fujiwara–Moritani reaction">Fujiwara–Moritani reaction</a></li> <li><a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gattermann_reaction" title="Gattermann reaction">Gattermann reaction</a></li> <li><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Hammick_reaction" title="Hammick reaction">Hammick reaction</a></li> <li><a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a></li> <li><a href="/wiki/Henry_reaction" title="Henry reaction">Henry reaction</a></li> <li><a href="/wiki/Heterogeneous_metal_catalyzed_cross-coupling" title="Heterogeneous metal catalyzed cross-coupling">Heterogeneous metal catalyzed cross-coupling</a></li> <li><a href="/wiki/High_dilution_principle" title="High dilution principle">High dilution principle</a></li> <li><a href="/wiki/Hiyama_coupling" title="Hiyama coupling">Hiyama coupling</a></li> <li><a href="/wiki/Homologation_reaction" title="Homologation reaction">Homologation reaction</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrocyanation" title="Hydrocyanation">Hydrocyanation</a></li> <li><a href="/wiki/Hydrovinylation" title="Hydrovinylation">Hydrovinylation</a></li> <li><a href="/wiki/Hydroxymethylation" title="Hydroxymethylation">Hydroxymethylation</a></li> <li><a href="/wiki/Ivanov_reaction" title="Ivanov reaction">Ivanov reaction</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kolbe%E2%80%93Schmitt_reaction" title="Kolbe–Schmitt reaction">Kolbe–Schmitt reaction</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a></li> <li><a href="/wiki/Liebeskind%E2%80%93Srogl_coupling" title="Liebeskind–Srogl coupling">Liebeskind–Srogl coupling</a></li> <li><a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">Malonic ester synthesis</a></li> <li><a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Meerwein_arylation" title="Meerwein arylation">Meerwein arylation</a></li> <li><a href="/wiki/Methylenation" title="Methylenation">Methylenation</a></li> <li><a href="/wiki/Michael_reaction" class="mw-redirect" title="Michael reaction">Michael reaction</a></li> <li><a href="/wiki/Minisci_reaction" title="Minisci reaction">Minisci reaction</a></li> <li><a href="/w/index.php?title=Mizoroki-Heck_vs._Reductive_Heck&action=edit&redlink=1" class="new" title="Mizoroki-Heck vs. Reductive Heck (page does not exist)">Mizoroki-Heck vs. Reductive Heck</a></li> <li><a href="/wiki/Nef_isocyanide_reaction" title="Nef isocyanide reaction">Nef isocyanide reaction</a></li> <li><a href="/wiki/Nef_synthesis" title="Nef synthesis">Nef synthesis</a></li> <li><a href="/wiki/Negishi_coupling" title="Negishi coupling">Negishi coupling</a></li> <li><a href="/wiki/Nierenstein_reaction" title="Nierenstein reaction">Nierenstein reaction</a></li> <li><a href="/wiki/Nitro-Mannich_reaction" title="Nitro-Mannich reaction">Nitro-Mannich reaction</a></li> <li><a href="/wiki/Nozaki%E2%80%93Hiyama%E2%80%93Kishi_reaction" title="Nozaki–Hiyama–Kishi reaction">Nozaki–Hiyama–Kishi reaction</a></li> <li><a href="/wiki/Olefin_conversion_technology" title="Olefin conversion technology">Olefin conversion technology</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Palladium%E2%80%93NHC_complex" title="Palladium–NHC complex">Palladium–NHC complex</a></li> <li><a href="/wiki/Passerini_reaction" title="Passerini reaction">Passerini reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Pfitzinger_reaction" title="Pfitzinger reaction">Pfitzinger reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a></li> <li><a href="/wiki/Prins_reaction" title="Prins reaction">Prins reaction</a></li> <li><a href="/wiki/Quelet_reaction" title="Quelet reaction">Quelet reaction</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Rauhut%E2%80%93Currier_reaction" title="Rauhut–Currier reaction">Rauhut–Currier reaction</a></li> <li><a href="/wiki/Reformatsky_reaction" title="Reformatsky reaction">Reformatsky reaction</a></li> <li><a href="/wiki/Reimer%E2%80%93Tiemann_reaction" title="Reimer–Tiemann reaction">Reimer–Tiemann reaction</a></li> <li><a href="/wiki/Rieche_formylation" title="Rieche formylation">Rieche formylation</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sakurai_reaction" title="Sakurai reaction">Sakurai reaction</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></li> <li><a href="/wiki/Stetter_reaction" title="Stetter reaction">Stetter reaction</a></li> <li><a href="/wiki/Stille_reaction" title="Stille reaction">Stille reaction</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Stork_enamine_alkylation" title="Stork enamine alkylation">Stork enamine alkylation</a></li> <li><a href="/wiki/Suzuki_reaction" title="Suzuki reaction">Suzuki reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Thorpe_reaction" title="Thorpe reaction">Thorpe reaction</a></li> <li><a href="/wiki/Ugi_reaction" title="Ugi reaction">Ugi reaction</a></li> <li><a href="/wiki/Ullmann_reaction" title="Ullmann reaction">Ullmann reaction</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li> <li><a href="/wiki/Weinreb_ketone_synthesis" title="Weinreb ketone synthesis">Weinreb ketone synthesis</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li> <li><a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a></li> <li><a href="/wiki/Wurtz%E2%80%93Fittig_reaction" title="Wurtz–Fittig reaction">Wurtz–Fittig reaction</a></li> <li><a href="/wiki/Zincke%E2%80%93Suhl_reaction" title="Zincke–Suhl reaction">Zincke–Suhl reaction</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Homologation_reactions" class="mw-redirect" title="Homologation reactions">Homologation reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Methoxymethylenetriphenylphosphorane" title="Methoxymethylenetriphenylphosphorane">Methoxymethylenetriphenylphosphorane</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Olefination reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a></li> <li><a href="/wiki/Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a></li> <li><a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Grieco_elimination" title="Grieco elimination">Grieco elimination</a></li> <li><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrazone_iodination" title="Hydrazone iodination">Hydrazone iodination</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-heteroatom <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azo_coupling" title="Azo coupling">Azo coupling</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Boudouard_reaction" title="Boudouard reaction">Boudouard reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Diazonium_compound" title="Diazonium compound">Diazonium compound</a></li> <li><a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Kharasch%E2%80%93Sosnovsky_reaction" title="Kharasch–Sosnovsky reaction">Kharasch–Sosnovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Leimgruber%E2%80%93Batcho_indole_synthesis" title="Leimgruber–Batcho indole synthesis">Leimgruber–Batcho indole synthesis</a></li> <li><a href="/wiki/Mukaiyama_hydration" title="Mukaiyama hydration">Mukaiyama hydration</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Oxymercuration_reaction" title="Oxymercuration reaction">Oxymercuration reaction</a></li> <li><a href="/wiki/Reed_reaction" title="Reed reaction">Reed reaction</a></li> <li><a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a></li> <li><a href="/wiki/Ullmann_condensation" title="Ullmann condensation">Ullmann condensation</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Yamaguchi_esterification" title="Yamaguchi esterification">Yamaguchi esterification</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Degradation <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbier%E2%80%93Wieland_degradation" title="Barbier–Wieland degradation">Barbier–Wieland degradation</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Edman_degradation" title="Edman degradation">Edman degradation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Gallagher%E2%80%93Hollander_degradation" title="Gallagher–Hollander degradation">Gallagher–Hollander degradation</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Isosaccharinic_acid" title="Isosaccharinic acid">Isosaccharinic acid</a></li> <li><a href="/wiki/Marker_degradation" title="Marker degradation">Marker degradation</a></li> <li><a href="/wiki/Ruff_degradation" title="Ruff degradation">Ruff degradation</a></li> <li><a href="/wiki/Strecker_degradation" title="Strecker degradation">Strecker degradation</a></li> <li><a href="/wiki/Von_Braun_amide_degradation" title="Von Braun amide degradation">Von Braun amide degradation</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Wohl_degradation" title="Wohl degradation">Wohl degradation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Organic redox <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Adkins%E2%80%93Peterson_reaction" title="Adkins–Peterson reaction">Adkins–Peterson reaction</a></li> <li><a href="/wiki/Akabori_amino-acid_reaction" title="Akabori amino-acid reaction">Akabori amino-acid reaction</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a></li> <li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Amide_reduction" title="Amide reduction">Amide reduction</a></li> <li><a href="/wiki/Andrussow_process" title="Andrussow process">Andrussow process</a></li> <li><a href="/wiki/Angeli%E2%80%93Rimini_reaction" title="Angeli–Rimini reaction">Angeli–Rimini reaction</a></li> <li><a href="/wiki/Aromatization" title="Aromatization">Aromatization</a></li> <li><a href="/wiki/Autoxidation" title="Autoxidation">Autoxidation</a></li> <li><a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a></li> <li><a href="/wiki/Barton%E2%80%93McCombie_deoxygenation" title="Barton–McCombie deoxygenation">Barton–McCombie deoxygenation</a></li> <li><a href="/wiki/Bechamp_reduction" class="mw-redirect" title="Bechamp reduction">Bechamp reduction</a></li> <li><a href="/wiki/Benkeser_reaction" class="mw-redirect" title="Benkeser reaction">Benkeser reaction</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a></li> <li><a href="/wiki/Bohn%E2%80%93Schmidt_reaction" title="Bohn–Schmidt reaction">Bohn–Schmidt reaction</a></li> <li><a href="/wiki/Bosch_reaction" title="Bosch reaction">Bosch reaction</a></li> <li><a href="/wiki/Bouveault%E2%80%93Blanc_reduction" title="Bouveault–Blanc reduction">Bouveault–Blanc reduction</a></li> <li><a href="/wiki/Boyland%E2%80%93Sims_oxidation" title="Boyland–Sims oxidation">Boyland–Sims oxidation</a></li> <li><a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Clemmensen_reduction" title="Clemmensen reduction">Clemmensen reduction</a></li> <li><a href="/wiki/Collins_oxidation" title="Collins oxidation">Collins oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Itsuno_reduction" title="Corey–Itsuno reduction">Corey–Itsuno reduction</a></li> <li><a href="/wiki/Corey%E2%80%93Kim_oxidation" title="Corey–Kim oxidation">Corey–Kim oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Criegee_oxidation" title="Criegee oxidation">Criegee oxidation</a></li> <li><a href="/wiki/Dakin_oxidation" title="Dakin oxidation">Dakin oxidation</a></li> <li><a href="/wiki/Davis_oxidation" title="Davis oxidation">Davis oxidation</a></li> <li><a href="/wiki/Deoxygenation" title="Deoxygenation">Deoxygenation</a></li> <li><a href="/wiki/Dess%E2%80%93Martin_oxidation" title="Dess–Martin oxidation">Dess–Martin oxidation</a></li> <li><a href="/wiki/DNA_oxidation" title="DNA oxidation">DNA oxidation</a></li> <li><a href="/wiki/Elbs_persulfate_oxidation" title="Elbs persulfate oxidation">Elbs persulfate oxidation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a></li> <li><a href="/wiki/%C3%89tard_reaction" title="Étard reaction">Étard reaction</a></li> <li><a href="/wiki/Fischer%E2%80%93Tropsch_process" title="Fischer–Tropsch process">Fischer–Tropsch process</a></li> <li><a href="/wiki/Fleming%E2%80%93Tamao_oxidation" title="Fleming–Tamao oxidation">Fleming–Tamao oxidation</a></li> <li><a href="/wiki/Fukuyama_reduction" title="Fukuyama reduction">Fukuyama reduction</a></li> <li><a href="/wiki/Ganem_oxidation" title="Ganem oxidation">Ganem oxidation</a></li> <li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li> <li><a href="/wiki/Griesbaum_coozonolysis" title="Griesbaum coozonolysis">Griesbaum coozonolysis</a></li> <li><a href="/wiki/Grundmann_aldehyde_synthesis" title="Grundmann aldehyde synthesis">Grundmann aldehyde synthesis</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">Hydrogenolysis</a></li> <li><a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a></li> <li><a href="/wiki/Jones_oxidation" title="Jones oxidation">Jones oxidation</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kolbe_electrolysis" title="Kolbe electrolysis">Kolbe electrolysis</a></li> <li><a href="/wiki/Kornblum_oxidation" title="Kornblum oxidation">Kornblum oxidation</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Leuckart_reaction" title="Leuckart reaction">Leuckart reaction</a></li> <li><a href="/wiki/Ley_oxidation" class="mw-redirect" title="Ley oxidation">Ley oxidation</a></li> <li><a href="/wiki/Lindgren_oxidation" title="Lindgren oxidation">Lindgren oxidation</a></li> <li><a href="/wiki/Lipid_peroxidation" title="Lipid peroxidation">Lipid peroxidation</a></li> <li><a href="/wiki/Lombardo_methylenation" title="Lombardo methylenation">Lombardo methylenation</a></li> <li><a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a></li> <li><a href="/wiki/Mark%C3%B3%E2%80%93Lam_deoxygenation" title="Markó–Lam deoxygenation">Markó–Lam deoxygenation</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/Meerwein%E2%80%93Ponndorf%E2%80%93Verley_reduction" title="Meerwein–Ponndorf–Verley reduction">Meerwein–Ponndorf–Verley reduction</a></li> <li><a href="/wiki/Methionine_sulfoxide" title="Methionine sulfoxide">Methionine sulfoxide</a></li> <li><a href="/wiki/Miyaura_borylation" title="Miyaura borylation">Miyaura borylation</a></li> <li><a href="/wiki/Mozingo_reduction" title="Mozingo reduction">Mozingo reduction</a></li> <li><a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a></li> <li><a href="/wiki/Omega_oxidation" title="Omega oxidation">Omega oxidation</a></li> <li><a href="/wiki/Oppenauer_oxidation" title="Oppenauer oxidation">Oppenauer oxidation</a></li> <li><a href="/wiki/Oxygen_rebound_mechanism" title="Oxygen rebound mechanism">Oxygen rebound mechanism</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Parikh%E2%80%93Doering_oxidation" title="Parikh–Doering oxidation">Parikh–Doering oxidation</a></li> <li><a href="/wiki/Pinnick_oxidation" title="Pinnick oxidation">Pinnick oxidation</a></li> <li><a href="/wiki/Pr%C3%A9vost_reaction" title="Prévost reaction">Prévost reaction</a></li> <li><a href="/wiki/Reduction_of_nitro_compounds" title="Reduction of nitro compounds">Reduction of nitro compounds</a></li> <li><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a></li> <li><a href="/wiki/Riley_oxidation" title="Riley oxidation">Riley oxidation</a></li> <li><a href="/wiki/Rosenmund_reduction" title="Rosenmund reduction">Rosenmund reduction</a></li> <li><a href="/wiki/Rubottom_oxidation" title="Rubottom oxidation">Rubottom oxidation</a></li> <li><a href="/wiki/Sabatier_reaction" title="Sabatier reaction">Sabatier reaction</a></li> <li><a href="/wiki/Sarett_oxidation" title="Sarett oxidation">Sarett oxidation</a></li> <li><a href="/wiki/Selenoxide_elimination" title="Selenoxide elimination">Selenoxide elimination</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sharpless_asymmetric_dihydroxylation" title="Sharpless asymmetric dihydroxylation">Sharpless asymmetric dihydroxylation</a></li> <li><a href="/wiki/Epoxidation_of_allylic_alcohols" title="Epoxidation of allylic alcohols">Epoxidation of allylic alcohols</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Sharpless_oxyamination" title="Sharpless oxyamination">Sharpless oxyamination</a></li> <li><a href="/wiki/Stahl_oxidation" title="Stahl oxidation">Stahl oxidation</a></li> <li><a href="/wiki/Staudinger_reaction" title="Staudinger reaction">Staudinger reaction</a></li> <li><a href="/wiki/Stephen_aldehyde_synthesis" title="Stephen aldehyde synthesis">Stephen aldehyde synthesis</a></li> <li><a href="/wiki/Swern_oxidation" title="Swern oxidation">Swern oxidation</a></li> <li><a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">Transfer hydrogenation</a></li> <li><a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a></li> <li><a href="/wiki/Wharton_reaction" title="Wharton reaction">Wharton reaction</a></li> <li><a href="/wiki/Whiting_reaction" title="Whiting reaction">Whiting reaction</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li> <li><a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner reduction</a></li> <li><a href="/wiki/Wolffenstein%E2%80%93B%C3%B6ters_reaction" title="Wolffenstein–Böters reaction">Wolffenstein–Böters reaction</a></li> <li><a href="/wiki/Zinin_reaction" title="Zinin reaction">Zinin reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,2-rearrangement" title="1,2-rearrangement">1,2-rearrangement</a></li> <li><a href="/wiki/1,2-Wittig_rearrangement" title="1,2-Wittig rearrangement">1,2-Wittig rearrangement</a></li> <li><a href="/wiki/2,3-sigmatropic_rearrangement" title="2,3-sigmatropic rearrangement">2,3-sigmatropic rearrangement</a></li> <li><a href="/wiki/2,3-Wittig_rearrangement" title="2,3-Wittig rearrangement">2,3-Wittig rearrangement</a></li> <li><a href="/wiki/Achmatowicz_reaction" title="Achmatowicz reaction">Achmatowicz reaction</a></li> <li><a href="/wiki/Alkyne_zipper_reaction" title="Alkyne zipper reaction">Alkyne zipper reaction</a></li> <li><a href="/wiki/Allen%E2%80%93Millar%E2%80%93Trippett_rearrangement" title="Allen–Millar–Trippett rearrangement">Allen–Millar–Trippett rearrangement</a></li> <li><a href="/wiki/Allylic_rearrangement" title="Allylic rearrangement">Allylic rearrangement</a></li> <li><a href="/wiki/Alpha-ketol_rearrangement" class="mw-redirect" title="Alpha-ketol rearrangement">Alpha-ketol rearrangement</a></li> <li><a href="/wiki/Amadori_rearrangement" title="Amadori rearrangement">Amadori rearrangement</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Aza-Cope_rearrangement" title="Aza-Cope rearrangement">Aza-Cope rearrangement</a></li> <li><a href="/wiki/Baker%E2%80%93Venkataraman_rearrangement" title="Baker–Venkataraman rearrangement">Baker–Venkataraman rearrangement</a></li> <li><a href="/wiki/Bamberger_rearrangement" title="Bamberger rearrangement">Bamberger rearrangement</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a></li> <li><a href="/wiki/Benzilic_acid_rearrangement" title="Benzilic acid rearrangement">Benzilic acid rearrangement</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Boekelheide_reaction" title="Boekelheide reaction">Boekelheide reaction</a></li> <li><a href="/wiki/Brook_rearrangement" title="Brook rearrangement">Brook rearrangement</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Carroll_rearrangement" title="Carroll rearrangement">Carroll rearrangement</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Cornforth_rearrangement" title="Cornforth rearrangement">Cornforth rearrangement</a></li> <li><a href="/wiki/Criegee_rearrangement" title="Criegee rearrangement">Criegee rearrangement</a></li> <li><a href="/wiki/Curtius_rearrangement" title="Curtius rearrangement">Curtius rearrangement</a></li> <li><a href="/wiki/Demjanov_rearrangement" title="Demjanov rearrangement">Demjanov rearrangement</a></li> <li><a href="/wiki/Di-%CF%80-methane_rearrangement" title="Di-π-methane rearrangement">Di-π-methane rearrangement</a></li> <li><a href="/wiki/Dimroth_rearrangement" title="Dimroth rearrangement">Dimroth rearrangement</a></li> <li><a href="/wiki/Divinylcyclopropane-cycloheptadiene_rearrangement" title="Divinylcyclopropane-cycloheptadiene rearrangement">Divinylcyclopropane-cycloheptadiene rearrangement</a></li> <li><a href="/wiki/Dowd%E2%80%93Beckwith_ring-expansion_reaction" title="Dowd–Beckwith ring-expansion reaction">Dowd–Beckwith ring-expansion reaction</a></li> <li><a href="/wiki/Electrocyclic_reaction" title="Electrocyclic reaction">Electrocyclic reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Favorskii_rearrangement" title="Favorskii rearrangement">Favorskii rearrangement</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Ferrier_rearrangement" title="Ferrier rearrangement">Ferrier rearrangement</a></li> <li><a href="/wiki/Fischer%E2%80%93Hepp_rearrangement" title="Fischer–Hepp rearrangement">Fischer–Hepp rearrangement</a></li> <li><a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a></li> <li><a href="/wiki/Fritsch%E2%80%93Buttenberg%E2%80%93Wiechell_rearrangement" title="Fritsch–Buttenberg–Wiechell rearrangement">Fritsch–Buttenberg–Wiechell rearrangement</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Group_transfer_reaction" title="Group transfer reaction">Group transfer reaction</a></li> <li><a href="/wiki/Halogen_dance_rearrangement" title="Halogen dance rearrangement">Halogen dance rearrangement</a></li> <li><a href="/wiki/Hayashi_rearrangement" title="Hayashi rearrangement">Hayashi rearrangement</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hofmann%E2%80%93Martius_rearrangement" title="Hofmann–Martius rearrangement">Hofmann–Martius rearrangement</a></li> <li><a href="/wiki/Ireland%E2%80%93Claisen_rearrangement" title="Ireland–Claisen rearrangement">Ireland–Claisen rearrangement</a></li> <li><a href="/wiki/Jacobsen_rearrangement" title="Jacobsen rearrangement">Jacobsen rearrangement</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Lobry_de_Bruyn%E2%80%93Van_Ekenstein_transformation" title="Lobry de Bruyn–Van Ekenstein transformation">Lobry de Bruyn–Van Ekenstein transformation</a></li> <li><a href="/wiki/Lossen_rearrangement" title="Lossen rearrangement">Lossen rearrangement</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/McLafferty_rearrangement" title="McLafferty rearrangement">McLafferty rearrangement</a></li> <li><a href="/wiki/Meyer%E2%80%93Schuster_rearrangement" title="Meyer–Schuster rearrangement">Meyer–Schuster rearrangement</a></li> <li><a href="/wiki/Mislow%E2%80%93Evans_rearrangement" title="Mislow–Evans rearrangement">Mislow–Evans rearrangement</a></li> <li><a href="/wiki/Mumm_rearrangement" title="Mumm rearrangement">Mumm rearrangement</a></li> <li><a href="/wiki/Myers_allene_synthesis" title="Myers allene synthesis">Myers allene synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Neber_rearrangement" title="Neber rearrangement">Neber rearrangement</a></li> <li><a href="/wiki/Newman%E2%80%93Kwart_rearrangement" title="Newman–Kwart rearrangement">Newman–Kwart rearrangement</a></li> <li><a href="/wiki/Overman_rearrangement" title="Overman rearrangement">Overman rearrangement</a></li> <li><a href="/wiki/Oxy-Cope_rearrangement" title="Oxy-Cope rearrangement">Oxy-Cope rearrangement</a></li> <li><a href="/wiki/Pericyclic_reaction" title="Pericyclic reaction">Pericyclic reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_rearrangement" title="Pinacol rearrangement">Pinacol rearrangement</a></li> <li><a href="/wiki/Pummerer_rearrangement" title="Pummerer rearrangement">Pummerer rearrangement</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Ring_expansion_and_contraction" title="Ring expansion and contraction">Ring expansion and contraction</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Rupe_reaction" class="mw-redirect" title="Rupe reaction">Rupe reaction</a></li> <li><a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a></li> <li><a href="/wiki/Semipinacol_rearrangement" title="Semipinacol rearrangement">Semipinacol rearrangement</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Sigmatropic_reaction" title="Sigmatropic reaction">Sigmatropic reaction</a></li> <li><a href="/wiki/Skatteb%C3%B8l_rearrangement" title="Skattebøl rearrangement">Skattebøl rearrangement</a></li> <li><a href="/wiki/Smiles_rearrangement" title="Smiles rearrangement">Smiles rearrangement</a></li> <li><a href="/wiki/Sommelet%E2%80%93Hauser_rearrangement" title="Sommelet–Hauser rearrangement">Sommelet–Hauser rearrangement</a></li> <li><a href="/wiki/Stevens_rearrangement" title="Stevens rearrangement">Stevens rearrangement</a></li> <li><a href="/wiki/Stieglitz_rearrangement" title="Stieglitz rearrangement">Stieglitz rearrangement</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Tiffeneau%E2%80%93Demjanov_rearrangement" title="Tiffeneau–Demjanov rearrangement">Tiffeneau–Demjanov rearrangement</a></li> <li><a href="/wiki/Vinylcyclopropane_rearrangement" title="Vinylcyclopropane rearrangement">Vinylcyclopropane rearrangement</a></li> <li><a href="/wiki/Wagner%E2%80%93Meerwein_rearrangement" title="Wagner–Meerwein rearrangement">Wagner–Meerwein rearrangement</a></li> <li><a href="/wiki/Wallach_rearrangement" title="Wallach rearrangement">Wallach rearrangement</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Westphalen%E2%80%93Lettr%C3%A9_rearrangement" title="Westphalen–Lettré rearrangement">Westphalen–Lettré rearrangement</a></li> <li><a href="/wiki/Willgerodt_rearrangement" title="Willgerodt rearrangement">Willgerodt rearrangement</a></li> <li><a href="/wiki/Wolff_rearrangement" title="Wolff rearrangement">Wolff rearrangement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/Annulation" title="Annulation">Annulation</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Baeyer%E2%80%93Emmerling_indole_synthesis" title="Baeyer–Emmerling indole synthesis">Baeyer–Emmerling indole synthesis</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bischler%E2%80%93M%C3%B6hlau_indole_synthesis" title="Bischler–Möhlau indole synthesis">Bischler–Möhlau indole synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Blum%E2%80%93Ittah_aziridine_synthesis" title="Blum–Ittah aziridine synthesis">Blum–Ittah aziridine synthesis</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Bohlmann%E2%80%93Rahtz_pyridine_synthesis" title="Bohlmann–Rahtz pyridine synthesis">Bohlmann–Rahtz pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Camps_quinoline_synthesis" title="Camps quinoline synthesis">Camps quinoline synthesis</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Davis%E2%80%93Beirut_reaction" title="Davis–Beirut reaction">Davis–Beirut reaction</a></li> <li><a href="/wiki/De_Kimpe_aziridine_synthesis" title="De Kimpe aziridine synthesis">De Kimpe aziridine synthesis</a></li> <li><a href="/wiki/Debus%E2%80%93Radziszewski_imidazole_synthesis" title="Debus–Radziszewski imidazole synthesis">Debus–Radziszewski imidazole synthesis</a></li> <li><a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Ferrario%E2%80%93Ackermann_reaction" title="Ferrario–Ackermann reaction">Ferrario–Ackermann reaction</a></li> <li><a href="/wiki/Fiesselmann_thiophene_synthesis" title="Fiesselmann thiophene synthesis">Fiesselmann thiophene synthesis</a></li> <li><a href="/wiki/Fischer_indole_synthesis" title="Fischer indole synthesis">Fischer indole synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Friedl%C3%A4nder_synthesis" title="Friedländer synthesis">Friedländer synthesis</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Graham_reaction" title="Graham reaction">Graham reaction</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hemetsberger_indole_synthesis" title="Hemetsberger indole synthesis">Hemetsberger indole synthesis</a></li> <li><a href="/wiki/Hofmann%E2%80%93L%C3%B6ffler_reaction" title="Hofmann–Löffler reaction">Hofmann–Löffler reaction</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Iodolactonization" title="Iodolactonization">Iodolactonization</a></li> <li><a href="/wiki/Isay_reaction" title="Isay reaction">Isay reaction</a></li> <li><a href="/wiki/Jacobsen_epoxidation" title="Jacobsen epoxidation">Jacobsen epoxidation</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Knorr_quinoline_synthesis" title="Knorr quinoline synthesis">Knorr quinoline synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Larock_indole_synthesis" title="Larock indole synthesis">Larock indole synthesis</a></li> <li><a href="/wiki/Madelung_synthesis" title="Madelung synthesis">Madelung synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Niementowski_quinoline_synthesis" title="Niementowski quinoline synthesis">Niementowski quinoline synthesis</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Patern%C3%B2%E2%80%93B%C3%BCchi_reaction" title="Paternò–Büchi reaction">Paternò–Büchi reaction</a></li> <li><a href="/wiki/Pechmann_condensation" title="Pechmann condensation">Pechmann condensation</a></li> <li><a href="/wiki/Petrenko-Kritschenko_piperidone_synthesis" title="Petrenko-Kritschenko piperidone synthesis">Petrenko-Kritschenko piperidone synthesis</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Pschorr_cyclization" title="Pschorr cyclization">Pschorr cyclization</a></li> <li><a href="/wiki/Reissert_indole_synthesis" title="Reissert indole synthesis">Reissert indole synthesis</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Simmons%E2%80%93Smith_reaction" title="Simmons–Smith reaction">Simmons–Smith reaction</a></li> <li><a href="/wiki/Skraup_reaction" title="Skraup reaction">Skraup reaction</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Van_Leusen_reaction" title="Van Leusen reaction">Van Leusen reaction</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/4%2B4_Photocycloaddition" title="4+4 Photocycloaddition">4+4 Photocycloaddition</a></li> <li><a href="/wiki/(4%2B3)_cycloaddition" title="(4+3) cycloaddition">(4+3) cycloaddition</a></li> <li><a href="/wiki/6%2B4_Cycloaddition" title="6+4 Cycloaddition">6+4 Cycloaddition</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Aza-Diels%E2%80%93Alder_reaction" title="Aza-Diels–Alder reaction">Aza-Diels–Alder reaction</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Bradsher_cycloaddition" title="Bradsher cycloaddition">Bradsher cycloaddition</a></li> <li><a href="/wiki/Cheletropic_reaction" title="Cheletropic reaction">Cheletropic reaction</a></li> <li><a href="/wiki/Conia-ene_reaction" title="Conia-ene reaction">Conia-ene reaction</a></li> <li><a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Enone%E2%80%93alkene_cycloadditions" title="Enone–alkene cycloadditions">Enone–alkene cycloadditions</a></li> <li><a href="/wiki/Hexadehydro_Diels%E2%80%93Alder_reaction" title="Hexadehydro Diels–Alder reaction">Hexadehydro Diels–Alder reaction</a></li> <li><a href="/wiki/Intramolecular_Diels%E2%80%93Alder_cycloaddition" title="Intramolecular Diels–Alder cycloaddition">Intramolecular Diels–Alder cycloaddition</a></li> <li><a href="/wiki/Inverse_electron-demand_Diels%E2%80%93Alder_reaction" title="Inverse electron-demand Diels–Alder reaction">Inverse electron-demand Diels–Alder reaction</a></li> <li><a href="/wiki/Ketene_cycloaddition" title="Ketene cycloaddition">Ketene cycloaddition</a></li> <li><a href="/wiki/McCormack_reaction" title="McCormack reaction">McCormack reaction</a></li> <li><a href="/wiki/Metal-centered_cycloaddition_reactions" title="Metal-centered cycloaddition reactions">Metal-centered cycloaddition reactions</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Oxo-Diels%E2%80%93Alder_reaction" title="Oxo-Diels–Alder reaction">Oxo-Diels–Alder reaction</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a></li> <li><a href="/wiki/Povarov_reaction" title="Povarov reaction">Povarov reaction</a></li> <li><a href="/wiki/Prato_reaction" title="Prato reaction">Prato reaction</a></li> <li><a href="/wiki/Retro-Diels%E2%80%93Alder_reaction" title="Retro-Diels–Alder reaction">Retro-Diels–Alder reaction</a></li> <li><a href="/wiki/Staudinger_synthesis" title="Staudinger synthesis">Staudinger synthesis</a></li> <li><a href="/wiki/Trimethylenemethane_cycloaddition" title="Trimethylenemethane cycloaddition">Trimethylenemethane cycloaddition</a></li> <li><a href="/wiki/Vinylcyclopropane_(5%2B2)_cycloaddition" title="Vinylcyclopropane (5+2) cycloaddition">Vinylcyclopropane (5+2) cycloaddition</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Heterocycle forming reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Bamberger_triazine_synthesis" title="Bamberger triazine synthesis">Bamberger triazine synthesis</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Barton%E2%80%93Zard_reaction" title="Barton–Zard reaction">Barton–Zard reaction</a></li> <li><a href="/wiki/Bernthsen_acridine_synthesis" title="Bernthsen acridine synthesis">Bernthsen acridine synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Boger_pyridine_synthesis" title="Boger pyridine synthesis">Boger pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Einhorn%E2%80%93Brunner_reaction" title="Einhorn–Brunner reaction">Einhorn–Brunner reaction</a></li> <li><a href="/wiki/Erlenmeyer%E2%80%93Pl%C3%B6chl_azlactone_and_amino-acid_synthesis" title="Erlenmeyer–Plöchl azlactone and amino-acid synthesis">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Hantzsch_ester" title="Hantzsch ester">Hantzsch ester</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Herz_reaction" title="Herz reaction">Herz reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/wiki/Lectka_enantioselective_beta-lactam_synthesis" title="Lectka enantioselective beta-lactam synthesis">Lectka enantioselective beta-lactam synthesis</a></li> <li><a href="/wiki/Lehmstedt%E2%80%93Tanasescu_reaction" title="Lehmstedt–Tanasescu reaction">Lehmstedt–Tanasescu reaction</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Pellizzari_reaction" title="Pellizzari reaction">Pellizzari reaction</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Robinson%E2%80%93Gabriel_synthesis" title="Robinson–Gabriel synthesis">Robinson–Gabriel synthesis</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" 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