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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Physical properties and characterization</span> </div> </a> <ul id="toc-Physical_properties_and_characterization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications_and_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications_and_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Applications and occurrence</span> </div> </a> <button aria-controls="toc-Applications_and_occurrence-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 Applications and occurrence subsection</span> </button> <ul id="toc-Applications_and_occurrence-sublist" class="vector-toc-list"> <li id="toc-Naturally_occurring_aldehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Naturally_occurring_aldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Naturally occurring aldehydes</span> </div> </a> <ul id="toc-Naturally_occurring_aldehydes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1"> <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-Hydroformylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydroformylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Hydroformylation</span> </div> </a> <ul id="toc-Hydroformylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidative_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidative_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Oxidative routes</span> </div> </a> <ul id="toc-Oxidative_routes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Specialty_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Specialty_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Specialty methods</span> </div> </a> <ul id="toc-Specialty_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Common_reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Common_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Common reactions</span> </div> </a> <button aria-controls="toc-Common_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 Common reactions subsection</span> </button> <ul id="toc-Common_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-Enolization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enolization"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Enolization</span> </div> </a> <ul id="toc-Enolization-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-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_addition_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_addition_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Nucleophilic addition reactions</span> </div> </a> <ul id="toc-Nucleophilic_addition_reactions-sublist" class="vector-toc-list"> <li id="toc-Oxygen_nucleophiles" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oxygen_nucleophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5.1</span> <span>Oxygen nucleophiles</span> </div> </a> <ul id="toc-Oxygen_nucleophiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nitrogen_nucleophiles" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Nitrogen_nucleophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5.2</span> <span>Nitrogen nucleophiles</span> </div> </a> <ul id="toc-Nitrogen_nucleophiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carbon_nucleophiles" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Carbon_nucleophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5.3</span> <span>Carbon nucleophiles</span> </div> </a> <ul id="toc-Carbon_nucleophiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bisulfite_reaction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Bisulfite_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5.4</span> <span>Bisulfite reaction</span> </div> </a> <ul id="toc-Bisulfite_reaction-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-More_complex_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#More_complex_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>More complex reactions</span> </div> </a> <ul id="toc-More_complex_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dialdehydes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Dialdehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dialdehydes</span> </div> </a> <ul id="toc-Dialdehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Examples_of_aldehydes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Examples_of_aldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Examples of aldehydes</span> </div> </a> <ul id="toc-Examples_of_aldehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Examples_of_dialdehydes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Examples_of_dialdehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Examples of dialdehydes</span> </div> </a> <ul id="toc-Examples_of_dialdehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-Nomenclature-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 Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-IUPAC_names_for_aldehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#IUPAC_names_for_aldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.1</span> <span>IUPAC names for aldehydes</span> </div> </a> <ul id="toc-IUPAC_names_for_aldehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Etymology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.2</span> <span>Etymology</span> </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</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">Aldehyde</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 82 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-82" 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">82 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/Aldehied" title="Aldehied – Afrikaans" lang="af" hreflang="af" data-title="Aldehied" 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%A3%D9%84%D8%AF%D9%87%D9%8A%D8%AF" title="ألدهيد – Arabic" lang="ar" hreflang="ar" data-title="ألدهيد" 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/Aldeh%C3%ADdu" title="Aldehídu – Asturian" lang="ast" hreflang="ast" data-title="Aldehídu" 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/Aldehidl%C9%99r" title="Aldehidlər – Azerbaijani" lang="az" hreflang="az" data-title="Aldehidlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="آلدهید – South Azerbaijani" lang="azb" hreflang="azb" data-title="آلدهید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%A1%E0%A6%BF%E0%A6%B9%E0%A6%BE%E0%A6%87%E0%A6%A1" title="অ্যালডিহাইড – Bangla" lang="bn" hreflang="bn" data-title="অ্যালডিহাইড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Aldehyde" title="Aldehyde – Minnan" lang="nan" hreflang="nan" data-title="Aldehyde" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%B4%D1%8D%D0%B3%D1%96%D0%B4%D1%8B" title="Альдэгіды – Belarusian" lang="be" hreflang="be" data-title="Альдэгіды" 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%90%D0%BB%D1%8C%D0%B4%D1%8D%D0%B3%D1%96%D0%B4%D1%8B" title="Альдэгіды – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Альдэгіды" 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/Aldehido" title="Aldehido – Central Bikol" lang="bcl" hreflang="bcl" data-title="Aldehido" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Алдехид – Bulgarian" lang="bg" hreflang="bg" data-title="Алдехид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bo mw-list-item"><a href="https://bo.wikipedia.org/wiki/%E0%BD%A8%E0%BD%A3%E0%BC%8B%E0%BD%8C%E0%BD%B2%E0%BC%8B%E0%BD%A7%E0%BC%8B%E0%BD%A1%E0%BD%B2%E0%BC%8B%E0%BD%8C%E0%BD%B2%E0%BC%8D" title="ཨལ་ཌི་ཧ་ཡི་ཌི། – Tibetan" lang="bo" hreflang="bo" data-title="ཨལ་ཌི་ཧ་ཡི་ཌི།" data-language-autonym="བོད་ཡིག" data-language-local-name="Tibetan" class="interlanguage-link-target"><span>བོད་ཡིག</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Aldehid" title="Aldehid – Bosnian" lang="bs" hreflang="bs" data-title="Aldehid" 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/Aldehid" title="Aldehid – Catalan" lang="ca" hreflang="ca" data-title="Aldehid" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Aldehydy" title="Aldehydy – Czech" lang="cs" hreflang="cs" data-title="Aldehydy" 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/Aldehyd" title="Aldehyd – Welsh" lang="cy" hreflang="cy" data-title="Aldehyd" 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/Aldehyd" title="Aldehyd – Danish" lang="da" hreflang="da" data-title="Aldehyd" 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/Aldehyde" title="Aldehyde – German" lang="de" hreflang="de" data-title="Aldehyde" 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/Aldeh%C3%BC%C3%BCdid" title="Aldehüüdid – Estonian" lang="et" hreflang="et" data-title="Aldehüüdid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%B4%CE%B5%CE%B0%CE%B4%CE%B5%CF%82" title="Αλδεΰδες – Greek" lang="el" hreflang="el" data-title="Αλδεΰδες" 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/Aldeh%C3%ADdo" title="Aldehído – Spanish" lang="es" hreflang="es" data-title="Aldehído" 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/Aldehido" title="Aldehido – Esperanto" lang="eo" hreflang="eo" data-title="Aldehido" 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/Aldehido" title="Aldehido – Basque" lang="eu" hreflang="eu" data-title="Aldehido" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%D8%AF%D8%A6%DB%8C%D8%AF" title="آلدئید – Persian" lang="fa" hreflang="fa" data-title="آلدئید" 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/Aldehyd" title="Aldehyd – Faroese" lang="fo" hreflang="fo" data-title="Aldehyd" 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/Ald%C3%A9hyde" title="Aldéhyde – French" lang="fr" hreflang="fr" data-title="Aldéhyde" 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/Aild%C3%A9ad" title="Aildéad – Irish" lang="ga" hreflang="ga" data-title="Aildéad" 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/Aldehido" title="Aldehido – Galician" lang="gl" hreflang="gl" data-title="Aldehido" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%EB%8D%B0%ED%95%98%EC%9D%B4%EB%93%9C" title="알데하이드 – Korean" lang="ko" hreflang="ko" data-title="알데하이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%AC%D5%A4%D5%A5%D5%B0%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Ալդեհիդներ – Armenian" lang="hy" hreflang="hy" data-title="Ալդեհիդներ" 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%8F%E0%A4%B2%E0%A5%8D%E0%A4%A1%E0%A4%BF%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1" title="एल्डिहाइड – Hindi" lang="hi" hreflang="hi" data-title="एल्डिहाइड" 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/Aldehidi" title="Aldehidi – Croatian" lang="hr" hreflang="hr" data-title="Aldehidi" 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/Alkanal" title="Alkanal – Indonesian" lang="id" hreflang="id" data-title="Alkanal" 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/Aldeidi" title="Aldeidi – Italian" lang="it" hreflang="it" data-title="Aldeidi" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%93%D7%94%D7%99%D7%93" title="אלדהיד – Hebrew" lang="he" hreflang="he" data-title="אלדהיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%B2%E0%B3%8D%E0%B2%A1%E0%B2%BF%E0%B2%B9%E0%B3%88%E0%B2%A1%E0%B3%81%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಆಲ್ಡಿಹೈಡುಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಆಲ್ಡಿಹೈಡುಗಳು" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%9A%E1%83%93%E1%83%94%E1%83%B0%E1%83%98%E1%83%93%E1%83%98" title="ალდეჰიდი – Georgian" lang="ka" hreflang="ka" data-title="ალდეჰიდი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4%D1%82%D0%B5%D1%80" title="Альдегидтер – Kazakh" lang="kk" hreflang="kk" data-title="Альдегидтер" 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%90%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4%D0%B4%D0%B5%D1%80" title="Альдегиддер – Kyrgyz" lang="ky" hreflang="ky" data-title="Альдегиддер" 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/Aldehydum" title="Aldehydum – Latin" lang="la" hreflang="la" data-title="Aldehydum" 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/Aldeh%C4%ABdi" title="Aldehīdi – Latvian" lang="lv" hreflang="lv" data-title="Aldehīdi" 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/Aldehidai" title="Aldehidai – Lithuanian" lang="lt" hreflang="lt" data-title="Aldehidai" 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/Aldehid" title="Aldehid – Hungarian" lang="hu" hreflang="hu" data-title="Aldehid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Алдехид – Macedonian" lang="mk" hreflang="mk" data-title="Алдехид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mzn mw-list-item"><a href="https://mzn.wikipedia.org/wiki/%D8%A2%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="آلدهید – Mazanderani" lang="mzn" hreflang="mzn" data-title="آلدهید" data-language-autonym="مازِرونی" data-language-local-name="Mazanderani" class="interlanguage-link-target"><span>مازِرونی</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Aldehid" title="Aldehid – Malay" lang="ms" hreflang="ms" data-title="Aldehid" 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/Aldehyde" title="Aldehyde – Dutch" lang="nl" hreflang="nl" data-title="Aldehyde" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%83%87%E3%83%92%E3%83%89" title="アルデヒド – Japanese" lang="ja" hreflang="ja" data-title="アルデヒド" 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/Aldehyd" title="Aldehyd – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Aldehyd" 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/Aldehyd" title="Aldehyd – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Aldehyd" 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/Alde%C3%AFd" title="Aldeïd – Occitan" lang="oc" hreflang="oc" data-title="Aldeïd" 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/Aldegidlar" title="Aldegidlar – Uzbek" lang="uz" hreflang="uz" data-title="Aldegidlar" 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%90%E0%A8%B2%E0%A8%A1%E0%A9%80%E0%A8%B9%E0%A8%BE%E0%A8%88%E0%A8%A1" title="ਐਲਡੀਹਾਈਡ – Punjabi" lang="pa" hreflang="pa" data-title="ਐਲਡੀਹਾਈਡ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%D9%84%DA%88%DB%8C%DB%81%D8%A7%D8%A6%DA%88" title="الڈیہائڈ – Western Punjabi" lang="pnb" hreflang="pnb" data-title="الڈیہائڈ" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%84%D8%AF%D9%8A%D9%87%D8%A7%D9%8A%D8%AF" title="الديهايد – Pashto" lang="ps" hreflang="ps" data-title="الديهايد" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Aldehyd" title="Aldehyd – Low German" lang="nds" hreflang="nds" data-title="Aldehyd" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Aldehydy" title="Aldehydy – Polish" lang="pl" hreflang="pl" data-title="Aldehydy" 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/Alde%C3%ADdo" title="Aldeído – Portuguese" lang="pt" hreflang="pt" data-title="Aldeído" 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/Aldehid%C4%83" title="Aldehidă – Romanian" lang="ro" hreflang="ro" data-title="Aldehidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4%D1%8B" title="Альдегиды – Russian" lang="ru" hreflang="ru" data-title="Альдегиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Aldehyde" title="Aldehyde – Simple English" lang="en-simple" hreflang="en-simple" data-title="Aldehyde" 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/Aldehyd" title="Aldehyd – Slovak" lang="sk" hreflang="sk" data-title="Aldehyd" 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/Aldehid" title="Aldehid – Slovenian" lang="sl" hreflang="sl" data-title="Aldehid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%DA%B5%D8%AF%DB%8C%DA%BE%D8%A7%DB%8C%D8%AF" title="ئەڵدیھاید – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەڵدیھاید" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Алдехид – Serbian" lang="sr" hreflang="sr" data-title="Алдехид" 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/Aldehid" title="Aldehid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Aldehid" 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/Aldehida" title="Aldehida – Sundanese" lang="su" hreflang="su" data-title="Aldehida" 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/Aldehydit" title="Aldehydit – Finnish" lang="fi" hreflang="fi" data-title="Aldehydit" 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/Aldehyd" title="Aldehyd – Swedish" lang="sv" hreflang="sv" data-title="Aldehyd" 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%86%E0%AE%B2%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%95%E0%AF%88%E0%AE%9F%E0%AF%81" title="ஆல்டிகைடு – Tamil" lang="ta" hreflang="ta" data-title="ஆல்டிகைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4%D0%BB%D0%B0%D1%80" title="Альдегидлар – Tatar" lang="tt" hreflang="tt" data-title="Альдегидлар" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%86%E0%B0%B2%E0%B1%8D%E0%B0%A1%E0%B0%BF%E0%B0%B9%E0%B1%88%E0%B0%A1%E0%B1%81" title="ఆల్డిహైడు – Telugu" lang="te" hreflang="te" data-title="ఆల్డిహైడు" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%A5%E0%B8%94%E0%B8%B5%E0%B9%84%E0%B8%AE%E0%B8%94%E0%B9%8C" title="แอลดีไฮด์ – Thai" lang="th" hreflang="th" data-title="แอลดีไฮด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D0%BB%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Алдегид – Tajik" lang="tg" hreflang="tg" data-title="Алдегид" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Aldehit" title="Aldehit – Turkish" lang="tr" hreflang="tr" data-title="Aldehit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D1%96%D0%B4%D0%B8" title="Альдегіди – Ukrainian" lang="uk" hreflang="uk" data-title="Альдегіди" 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/Aldehyde" title="Aldehyde – Vietnamese" lang="vi" hreflang="vi" data-title="Aldehyde" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%86%9B" title="醛 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="醛" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aldehido" title="Aldehido – Waray" lang="war" hreflang="war" data-title="Aldehido" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%86%9B" title="醛 – Wu" lang="wuu" hreflang="wuu" data-title="醛" data-language-autonym="吴语" data-language-local-name="Wu" 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nomobile noexcerpt noprint searchaux" style="display:none">Organic compound containing the functional group R−CH=O</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Aldehyde_general_structure.svg" class="mw-file-description"><img alt="Aldehyde structure" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/220px-Aldehyde_general_structure.svg.png" decoding="async" width="220" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/330px-Aldehyde_general_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/440px-Aldehyde_general_structure.svg.png 2x" data-file-width="230" data-file-height="210" /></a><figcaption>Aldehyde structure</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>aldehyde</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'l' in 'lie'">l</span><span title="'d' in 'dye'">d</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'h' in 'hi'">h</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'d' in 'dye'">d</span></span>/</a></span></span>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> containing a <a href="/wiki/Functional_group" title="Functional group">functional group</a> with the structure <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−CH=O</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> The functional group itself (without the "R" <a href="/wiki/Side_chain" title="Side chain">side chain</a>) can be referred to as an <b>aldehyde</b> but can also be classified as a <b>formyl group</b>. Aldehydes are a common motif in many chemicals important in technology and biology.<sup id="cite_ref-March_2-0" class="reference"><a href="#cite_note-March-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp<sup>2</sup>-<a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybridized</a>. The aldehyde group is somewhat <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar</a>. The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=O</span> bond length is about 120–122 <a href="/wiki/Picometer" class="mw-redirect" title="Picometer">picometers</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties_and_characterization">Physical properties and characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=2" title="Edit section: Physical properties and characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> are soluble in water, and the volatile aldehydes have pungent odors. </p><p>Aldehydes can be identified by spectroscopic methods. Using <a href="/wiki/IR_spectroscopy" class="mw-redirect" title="IR spectroscopy">IR spectroscopy</a>, they display a strong <i>ν</i><sub>CO</sub> band near 1700 cm<sup>−1</sup>. In their <a href="/wiki/Proton_nuclear_magnetic_resonance" title="Proton nuclear magnetic resonance"><sup>1</sup>H NMR</a> spectra, the formyl hydrogen center absorbs near <i>δ</i><sub>H</sub> 9.5 to 10, which is a distinctive part of the spectrum. This signal shows the characteristic coupling to any protons on the α carbon with a small coupling constant typically less than 3.0 Hz. The <sup>13</sup>C NMR spectra of aldehydes and ketones gives a suppressed (weak) but distinctive signal at <i>δ</i><sub>C</sub> 190 to 205. </p> <div class="mw-heading mw-heading2"><h2 id="Applications_and_occurrence">Applications and occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=3" title="Edit section: Applications and occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Important_Aldehyde_Structures.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Important_Aldehyde_Structures.svg/830px-Important_Aldehyde_Structures.svg.png" decoding="async" width="830" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Important_Aldehyde_Structures.svg/1245px-Important_Aldehyde_Structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Important_Aldehyde_Structures.svg/1660px-Important_Aldehyde_Structures.svg.png 2x" data-file-width="1718" data-file-height="292" /></a><figcaption></figcaption></figure><p> Important aldehydes and related compounds. The <b>aldehyde group</b> (or <b>formyl group</b>) is colored red. From the left: (1) <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and (2) its trimer <a href="/wiki/1,3,5-Trioxane" title="1,3,5-Trioxane">1,3,5-trioxane</a>, (3) <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> and (4) its enol <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a>, (5) <a href="/wiki/Glucose" title="Glucose">glucose</a> (pyranose form as α-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucopyranose), (6) the flavorant <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a>, (7) <a href="/wiki/Retinal" title="Retinal">retinal</a>, which forms with <a href="/wiki/Opsin" title="Opsin">opsins</a> <a href="/wiki/Photoreceptor_protein" title="Photoreceptor protein">photoreceptors</a>, and (8) the vitamin <a href="/wiki/Pyridoxal" title="Pyridoxal">pyridoxal</a>. </p><div class="mw-heading mw-heading3"><h3 id="Naturally_occurring_aldehydes">Naturally occurring aldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=4" title="Edit section: Naturally occurring aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Traces of many aldehydes are found in <a href="/wiki/Essential_oil" title="Essential oil">essential oils</a> and often contribute to their pleasant odours, including <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a>, <a href="/wiki/Cilantro" class="mw-redirect" title="Cilantro">cilantro</a>, and <a href="/wiki/Vanillin" title="Vanillin">vanillin</a>. Possibly due to the high reactivity of the formyl group, aldehydes are not commonly found in organic "building block" molecules, such as amino acids, nucleic acids, and lipids. However, most sugars are derivatives of aldehydes. These <a href="/wiki/Aldose" title="Aldose">aldoses</a> exist as <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetals</a>, a sort of masked form of the parent aldehyde. For example, in aqueous solution only a tiny fraction of glucose exists as the aldehyde. </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=Aldehyde&action=edit&section=5" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Hydroformylation">Hydroformylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=6" title="Edit section: Hydroformylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Of the several methods for preparing aldehydes,<sup id="cite_ref-March_2-1" class="reference"><a href="#cite_note-March-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> one dominant technology is <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a>.<sup id="cite_ref-Bertleff_5-0" class="reference"><a href="#cite_note-Bertleff-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Hydroformylation is conducted on a very large scale for diverse aldehydes. It involves treatment of the alkene with a mixture of hydrogen gas and carbon monoxide in the presence of a metal catalyst. Illustrative is the generation of <a href="/wiki/Butyraldehyde" title="Butyraldehyde">butyraldehyde</a> by <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> of <a href="/wiki/Propylene" title="Propylene">propylene</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub> + CO + CH<sub class="template-chem2-sub">3</sub>CH=CH<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CHO</span></dd></dl> <p>One complication with this process is the formation of isomers, such as isobutyraldehyde: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub> + CO + CH<sub class="template-chem2-sub">3</sub>CH=CH<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>CH(CHO)CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Oxidative_routes">Oxidative routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=7" title="Edit section: Oxidative routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The largest operations involve <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> respectively to <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>, which are produced on multimillion ton scale annually. Other large scale aldehydes are produced by <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> of hydrocarbons: <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a> from <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/Acrolein" title="Acrolein">acrolein</a> from <a href="/wiki/Propylene" title="Propylene">propylene</a>, and <a href="/wiki/Methacrolein" title="Methacrolein">methacrolein</a> from <a href="/wiki/Isobutene" class="mw-redirect" title="Isobutene">isobutene</a>.<sup id="cite_ref-Ullmann_6-0" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CH2O_7-0" class="reference"><a href="#cite_note-CH2O-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>, oxidation of ethylene to acetaldehyde in the presence of copper and palladium catalysts, is also used. "<a href="/wiki/Green_chemistry" title="Green chemistry">Green</a>" and cheap oxygen (or air) is the oxidant of choice. </p><p>Laboratories may instead apply a wide variety of specialized <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agents</a>, which are often consumed stoichiometrically. <a href="/wiki/Oxidation_with_chromium(VI)_complexes" title="Oxidation with chromium(VI) complexes">chromium(VI) reagents are popular</a>. Oxidation can be achieved by heating the alcohol with an acidified solution of <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a>. In this case, excess <a href="/wiki/Dichromate" class="mw-redirect" title="Dichromate">dichromate</a> will further oxidize the aldehyde to a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, so either the aldehyde is <a href="/wiki/Distillation" title="Distillation">distilled</a> out as it forms (if <a href="/wiki/Vapor_pressure" title="Vapor pressure">volatile</a>) or milder reagents such as <a href="/wiki/Pyridinium_chlorochromate" title="Pyridinium chlorochromate">PCC</a> are used.<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> </p><p>A variety of reagent systems achieve aldehydes under chromium-free conditions. One such are the <a href="/wiki/Hypervalent_organoiodine_compounds" title="Hypervalent organoiodine compounds">hypervalent organoiodine compounds</a> (i.e., <a href="/wiki/2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">IBX acid</a>, <a href="/wiki/Dess%E2%80%93Martin_periodinane" title="Dess–Martin periodinane">Dess–Martin periodinane</a>), although these often <a href="/wiki/Carbonyl_oxidation_with_hypervalent_iodine_reagents" title="Carbonyl oxidation with hypervalent iodine reagents">also oxidize the α position</a>. A <a href="/wiki/Lux-Flood_acid" class="mw-redirect" title="Lux-Flood acid">Lux-Flood acid</a> will activate other pre-oxidized substrates: <a href="/wiki/Sulfonium-based_oxidation_of_alcohols_to_aldehydes" title="Sulfonium-based oxidation of alcohols to aldehydes">various sulfoxides</a> (e.g. the <a href="/wiki/Swern_oxidation" title="Swern oxidation">Swern oxidation</a>), or amine oxides (e.g., the <a href="/wiki/Ganem_oxidation" title="Ganem oxidation">Ganem oxidation</a>). Sterically-hindered <a href="/wiki/Nitroxyl" title="Nitroxyl">nitroxyls</a> (i.e., <a href="/wiki/TEMPO" title="TEMPO">TEMPO</a>) can <a href="/wiki/Oxoammonium-catalyzed_oxidation" title="Oxoammonium-catalyzed oxidation">catalyze aldehyde formation with a cheaper oxidant</a>. </p><p>Alternatively, <a href="/wiki/Vicinal_diol" class="mw-redirect" title="Vicinal diol">vicinal diols</a> or their <a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">oxidized sequelae</a> (<a href="/wiki/Acyloin" title="Acyloin">acyloins</a> or <a href="/wiki/Alpha_hydroxy_acid" class="mw-redirect" title="Alpha hydroxy acid">α-hydroxy acids</a>) can be oxidized with <a href="/wiki/Bond_cleavage" title="Bond cleavage">cleavage</a> to two aldehydes or an aldehyde and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><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> <div class="mw-heading mw-heading3"><h3 id="Specialty_methods">Specialty methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=8" title="Edit section: Specialty methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable" style="background-color:white;float: center; border-collapse: collapse; margin: 0em 1em;" border="1" cellpadding="2" cellspacing="0"> <tbody><tr> <th width="220px">Reaction name</th> <th>Substrate</th> <th class="unsortable">Comment </th></tr> <tr> <td valign="top"><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkenes</a> </td> <td>Reductive <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a>; similar effect with <a href="/wiki/Singlet_oxygen" title="Singlet oxygen">singlet oxygen</a> and no work-up </td></tr> <tr> <td valign="top"><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a> </td> <td><a href="/wiki/Ester" title="Ester">Esters</a>, <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a> </td> <td>Reduction of an <a href="/wiki/Ester" title="Ester">ester</a> with diisobutylaluminium hydride (<a href="/wiki/DIBAL-H" class="mw-redirect" title="DIBAL-H">DIBAL-H</a>) or <a href="/wiki/Sodium_aluminium_hydride" title="Sodium aluminium hydride">sodium aluminium hydride</a>; see also <a href="/wiki/Amide_reduction" title="Amide reduction">amide reduction</a>. </td></tr> <tr> <td valign="top"><a href="/wiki/Rosenmund_reaction" class="mw-redirect" title="Rosenmund reaction">Rosenmund reaction</a> </td> <td valign="top"><a href="/wiki/Acyl_chloride" title="Acyl chloride">Acyl chlorides</a> </td> <td>Acyl chlorides selectively <a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">reduced</a> to aldehydes. Lithium tri-<i>t</i>-butoxyaluminium hydride (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">LiAlH(O<sup class="template-chem2-sup"><i>t</i></sup>Bu)<sub class="template-chem2-sub">3</sub></span>) is an effective reagent.<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. (February 2016)">citation needed</span></a></i>]</sup> </td></tr> <tr> <td valign="top"><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> </td> <td valign="top"><a href="/wiki/Ketone" title="Ketone">Ketones</a> </td> <td>A modified Wittig reaction using <a href="/wiki/Methoxymethylenetriphenylphosphine" class="mw-redirect" title="Methoxymethylenetriphenylphosphine">methoxymethylenetriphenylphosphine</a> as a reagent. </td></tr> <tr> <td valign="top"><a href="/wiki/Formylation_reaction" class="mw-redirect" title="Formylation reaction">Formylation reactions</a> </td> <td valign="top"><a href="/wiki/Nucleophile" title="Nucleophile">Nucleophilic</a> <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">arenes</a> </td> <td>Various reactions, for example the <a href="/wiki/Vilsmeier-Haack_reaction" class="mw-redirect" title="Vilsmeier-Haack reaction">Vilsmeier-Haack reaction</a>. </td></tr> <tr> <td valign="top"><a href="/wiki/Nef_reaction" title="Nef reaction">Nef reaction</a> </td> <td valign="top"><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro compounds</a> </td> <td>The <a href="/wiki/Acid_catalysis" title="Acid catalysis">acid</a> <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of a <a href="/wiki/Primary_(chemistry)" title="Primary (chemistry)">primary</a> nitro compound to form an aldehyde. </td></tr> <tr> <td valign="top"><a href="/wiki/Kornblum_oxidation" title="Kornblum oxidation">Kornblum oxidation</a> </td> <td valign="top"><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkanes</a> </td> <td>The oxidation of primary halide with <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">dimethyl sulfoxide</a> to form an aldehyde. </td></tr> <tr> <td valign="top"><a href="/wiki/Zincke_reaction" title="Zincke reaction">Zincke reaction</a> </td> <td valign="top"><a href="/wiki/Pyridine" title="Pyridine">Pyridines</a> </td> <td><a href="/wiki/Zincke_aldehyde" title="Zincke aldehyde">Zincke aldehydes</a> formed in a reaction variation. </td></tr> <tr> <td valign="top"><a href="/wiki/Stephen_aldehyde_synthesis" title="Stephen aldehyde synthesis">Stephen aldehyde synthesis</a> </td> <td valign="top"><a href="/wiki/Nitrile" title="Nitrile">Nitriles</a> </td> <td>Hydrolysis of an <a href="/wiki/Iminium" title="Iminium">iminium</a> salt generated by <a href="/wiki/Tin(II)_chloride" title="Tin(II) chloride">tin(II) chloride</a> and <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a> to form an aldehyde. </td></tr> <tr> <td valign="top"><a href="/wiki/Geminal_halide_hydrolysis" title="Geminal halide hydrolysis">Geminal halide hydrolysis</a> </td> <td valign="top"><a href="/wiki/Geminal" title="Geminal">Geminal</a> <a href="/wiki/Halocarbon" title="Halocarbon">dihalides</a> </td> <td>Hydrolysis of <a href="/wiki/Primary_(chemistry)" title="Primary (chemistry)">primary</a> geminal dihalides to yield aldehydes. </td></tr> <tr> <td valign="top"><a href="/wiki/Meyers_synthesis" title="Meyers synthesis">Meyers synthesis</a> </td> <td valign="top"><a href="/wiki/Oxazine" class="mw-redirect" title="Oxazine">Oxazines</a> </td> <td><a href="/wiki/Hemiaminal" title="Hemiaminal">Hemiaminal</a> oxazine hydrolysis with water and <a href="/wiki/Oxalic_acid" title="Oxalic acid">oxalic acid</a> to yield an aldehyde. </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a> variation<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><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> </td> <td valign="top"><a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">Unsaturated</a> or <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon">α</a>-<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxy</a> <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a> </td> <td>Aldehydes via the hydrolysis of an <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediate</a> <a href="/wiki/Carbamic_acid" title="Carbamic acid">carbamate</a>. </td></tr> <tr> <td valign="top"><a href="/wiki/McFadyen-Stevens_reaction" class="mw-redirect" title="McFadyen-Stevens reaction">McFadyen-Stevens reaction</a> </td> <td valign="top"><a href="/wiki/Hydrazide" title="Hydrazide">Hydrazides</a> </td> <td><a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base</a>-<a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> of acylsulfonylhydrazides. </td></tr> <tr> <td valign="top"><a href="/wiki/Biotransformation" title="Biotransformation">Biotransformation</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkenes</a> </td> <td><a href="/wiki/Lyophilized" class="mw-redirect" title="Lyophilized">Lyophilized</a> cell cultures of <i><a href="/wiki/Trametes_hirsuta" title="Trametes hirsuta">Trametes hirsuta</a></i> in the presence of oxygen.<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> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Common_reactions">Common reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=9" title="Edit section: Common reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aldehydes participate in many reactions.<sup id="cite_ref-March_2-2" class="reference"><a href="#cite_note-March-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> From the industrial perspective, important reactions are: </p> <ul><li>condensations, e.g., to prepare <a href="/wiki/Plasticizers" class="mw-redirect" title="Plasticizers">plasticizers</a> and <a href="/wiki/Polyols" class="mw-redirect" title="Polyols">polyols</a>, and</li> <li>reduction to produce alcohols, especially "oxo-alcohols". From the biological perspective, the key reactions involve addition of nucleophiles to the formyl carbon in the formation of imines (oxidative deamination) and hemiacetals (structures of aldose sugars).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-March_2-3" class="reference"><a href="#cite_note-March-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul> <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=Aldehyde&action=edit&section=10" title="Edit section: Acid-base reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance stabilization</a> of the conjugate base, an <a href="/wiki/Alpha_hydrogen" class="mw-redirect" title="Alpha hydrogen">α-hydrogen</a> in an aldehyde is weakly <a href="/wiki/Acid" title="Acid">acidic</a> with a <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> near 17. Note, however, this is much more acidic than an alkane or ether hydrogen, which has <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> near 50 approximately, and is even more acidic than a ketone α-hydrogen which has <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> near 20. This acidification of the α-hydrogen in aldehyde is attributed to: </p> <ul><li>the electron-withdrawing quality of the formyl center and</li> <li>the fact that the conjugate base, an <a href="/wiki/Enolate" title="Enolate">enolate</a> anion, delocalizes its negative charge.</li></ul> <p>The formyl proton itself does not readily undergo deprotonation. </p> <div class="mw-heading mw-heading3"><h3 id="Enolization">Enolization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=11" title="Edit section: Enolization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aldehydes (except those without an alpha carbon, or without protons on the alpha carbon, such as formaldehyde and benzaldehyde) can exist in either the <a href="/wiki/Ketone" title="Ketone">keto</a> or the <a href="/wiki/Enol" title="Enol">enol</a> <a href="/wiki/Tautomer" title="Tautomer">tautomer</a>. <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">Keto–enol tautomerism</a> is catalyzed by either acid or base. In neutral solution, the enol is the minority tautomer, reversing several times per second.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> But it becomes the dominant tautomer in strong acid or base solutions, and enolized aldehydes undergo <a href="/wiki/Carbonyl_alpha-substitution_reactions" class="mw-redirect" title="Carbonyl alpha-substitution reactions">nucleophilic attack at the α position</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </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=Aldehyde&action=edit&section=12" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Aldehyde_reduction" class="mw-redirect" title="Aldehyde reduction">Aldehyde reduction</a></div> <p>The formyl group can be readily reduced to a <a href="/wiki/Primary_alcohol" title="Primary alcohol">primary alcohol</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>OH</span>). Typically this conversion is accomplished by catalytic <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> either directly or by <a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">transfer hydrogenation</a>. <a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometric</a> reductions are also popular, as can be effected with <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=13" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The formyl group readily oxidizes to the corresponding <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COOH</span>). The preferred oxidant in industry is oxygen or air. In the laboratory, popular oxidizing agents include <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a>, <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>, <a href="/wiki/Chromium_trioxide" title="Chromium trioxide">chromium(VI) oxide</a>, and <a href="/wiki/Chromic_acid" title="Chromic acid">chromic acid</a>. The combination of <a href="/wiki/Manganese_dioxide" title="Manganese dioxide">manganese dioxide</a>, <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> and <a href="/wiki/Methanol" title="Methanol">methanol</a> will convert the aldehyde to a methyl <a href="/wiki/Ester" title="Ester">ester</a>.<sup id="cite_ref-March_2-4" class="reference"><a href="#cite_note-March-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Another oxidation reaction is the basis of the <i>silver-mirror test</i>. In this test, an aldehyde is treated with <a href="/wiki/Tollens%27_reagent" title="Tollens' reagent">Tollens' reagent</a>, which is prepared by adding a drop of <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> solution into <a href="/wiki/Silver_nitrate" title="Silver nitrate">silver nitrate</a> solution to give a precipitate of silver(I) oxide, and then adding just enough dilute <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> solution to redissolve the precipitate in aqueous ammonia to produce <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ag(NH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">+</sup></span> complex. This reagent converts aldehydes to carboxylic acids without attacking carbon–carbon double bonds. The name <i>silver-mirror test</i> arises because this reaction produces a precipitate of silver, whose presence can be used to test for the presence of an aldehyde. </p><p>A further oxidation reaction involves <a href="/wiki/Fehling%27s_reagent" class="mw-redirect" title="Fehling's reagent">Fehling's reagent</a> as a test. The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cu<sup>2+</sup></span> complex ions are reduced to a red-brick-coloured <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Copper(I)_oxide" title="Copper(I) oxide">Cu<sub class="template-chem2-sub">2</sub>O</a></span> precipitate. </p><p>If the aldehyde cannot form an enolate (e.g., <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a>), addition of strong base induces the <a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a>. This reaction results in <a href="/wiki/Disproportionation" title="Disproportionation">disproportionation</a>, producing a mixture of alcohol and carboxylic acid. </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_addition_reactions">Nucleophilic addition reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=14" title="Edit section: Nucleophilic addition reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Nucleophile" title="Nucleophile">Nucleophiles</a> add readily to the carbonyl group. In the product, the carbonyl carbon becomes sp<sup>3</sup>-hybridized, being bonded to the nucleophile, and the oxygen center becomes protonated: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCHO + Nu<sup class="template-chem2-sup">−</sup> → RCH(Nu)O<sup class="template-chem2-sup">−</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH(Nu)O<sup class="template-chem2-sup">−</sup> + H<sup class="template-chem2-sup">+</sup> → RCH(Nu)OH</span></dd></dl> <p>In many cases, a water molecule is removed after the addition takes place; in this case, the reaction is classed as an <a href="/wiki/Addition_reaction" title="Addition reaction">addition</a>–<a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination</a> or <a href="/wiki/Addition_reaction" title="Addition reaction">addition</a>–<a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a>. There are many variations of nucleophilic addition reactions. </p> <div class="mw-heading mw-heading4"><h4 id="Oxygen_nucleophiles">Oxygen nucleophiles</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=15" title="Edit section: Oxygen nucleophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Acetalisation" class="mw-redirect" title="Acetalisation">acetalisation</a> reaction, under <a href="/wiki/Acid" title="Acid">acidic</a> or <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> conditions, an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> adds to the carbonyl group and a proton is transferred to form a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a>. Under <a href="/wiki/Acid" title="Acid">acidic</a> conditions, the hemiacetal and the alcohol can further react to form an <a href="/wiki/Acetal" title="Acetal">acetal</a> and water. Simple hemiacetals are usually unstable, although cyclic ones such as <a href="/wiki/Glucose" title="Glucose">glucose</a> can be stable. Acetals are stable, but revert to the aldehyde in the presence of acid. Aldehydes can react with water to form <a href="/wiki/Hydrate" title="Hydrate">hydrates</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH(OH)<sub class="template-chem2-sub">2</sub></span>. These diols are stable when strong <a href="/wiki/Electron_withdrawing_group" class="mw-redirect" title="Electron withdrawing group">electron withdrawing groups</a> are present, as in <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>. The mechanism of formation is identical to hemiacetal formation. </p> <div class="mw-heading mw-heading4"><h4 id="Nitrogen_nucleophiles">Nitrogen nucleophiles</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=16" title="Edit section: Nitrogen nucleophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Alkylimino-de-oxo-bisubstitution" class="mw-redirect" title="Alkylimino-de-oxo-bisubstitution">alkylimino-de-oxo-bisubstitution</a>, a primary or secondary amine adds to the carbonyl group and a proton is transferred from the nitrogen to the oxygen atom to create a <a href="/wiki/Carbinolamine" class="mw-redirect" title="Carbinolamine">carbinolamine</a>. In the case of a primary amine, a water molecule can be eliminated from the carbinolamine intermediate to yield an <a href="/wiki/Imine" title="Imine">imine</a> or its trimer, a <a href="/wiki/Hexahydrotriazine" class="mw-redirect" title="Hexahydrotriazine">hexahydrotriazine</a> This reaction is catalyzed by acid. <a href="/wiki/Hydroxylamine" title="Hydroxylamine">Hydroxylamine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">2</sub>OH</span>) can also add to the carbonyl group. After the elimination of water, this results in an <a href="/wiki/Oxime" title="Oxime">oxime</a>. An <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> derivative of the form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>NNR<sub class="template-chem2-sub">2</sub></span> such as <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>NNH<sub class="template-chem2-sub">2</sub></span>) or <a href="/wiki/2,4-dinitrophenylhydrazine" class="mw-redirect" title="2,4-dinitrophenylhydrazine">2,4-dinitrophenylhydrazine</a> can also be the nucleophile and after the elimination of water, resulting in the formation of a <a href="/wiki/Hydrazone" title="Hydrazone">hydrazone</a>, which are usually orange crystalline solids. This reaction forms the basis of a test for aldehydes and <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">ketones</a>.<sup id="cite_ref-Fuson_18-0" class="reference"><a href="#cite_note-Fuson-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Carbon_nucleophiles">Carbon nucleophiles</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=17" title="Edit section: Carbon nucleophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Cyanide" title="Cyanide">cyano</a> group in <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a> can add to the carbonyl group to form <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrins</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH(OH)CN</span>. In this reaction the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span> ion is the <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> that attacks the partially positive carbon atom of the <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carbonyl group</a>. The mechanism involves a pair of electrons from the carbonyl-group double bond transferring to the oxygen atom, leaving it single-bonded to carbon and giving the oxygen atom a negative charge. This intermediate ion rapidly reacts with <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup></span>, such as from the HCN molecule, to form the alcohol group of the cyanohydrin. </p><p><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic compounds</a>, such as <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a>, <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a>, or <a href="/wiki/Acetylide" title="Acetylide">acetylides</a>, undergo <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> reactions, yielding a substituted alcohol group. Related reactions include <a href="/wiki/Organostannane_addition" title="Organostannane addition">organostannane additions</a>, <a href="/wiki/Barbier_reaction" title="Barbier reaction">Barbier reactions</a>, and the <a href="/wiki/Nozaki%E2%80%93Hiyama%E2%80%93Kishi_reaction" title="Nozaki–Hiyama–Kishi reaction">Nozaki–Hiyama–Kishi reaction</a>. </p><p>In the <a href="/wiki/Aldol_reaction" title="Aldol reaction">aldol reaction</a>, the metal <a href="/wiki/Enolates" class="mw-redirect" title="Enolates">enolates</a> of <a href="/wiki/Ketone" title="Ketone">ketones</a>, <a href="/wiki/Ester" title="Ester">esters</a>, <a href="/wiki/Amide" title="Amide">amides</a>, and <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">carboxylic acids</a> add to aldehydes to form β-hydroxycarbonyl compounds (<a href="/wiki/Aldol" title="Aldol">aldols</a>). Acid or base-catalyzed dehydration then leads to α,β-unsaturated carbonyl compounds. The combination of these two steps is known as the <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a>. </p><p>The <a href="/wiki/Prins_reaction" title="Prins reaction">Prins reaction</a> occurs when a nucleophilic <a href="/wiki/Alkene" title="Alkene">alkene</a> or <a href="/wiki/Alkyne" title="Alkyne">alkyne</a> reacts with an aldehyde as electrophile. The product of the Prins reaction varies with reaction conditions and substrates employed. </p> <div class="mw-heading mw-heading4"><h4 id="Bisulfite_reaction">Bisulfite reaction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=18" title="Edit section: Bisulfite reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aldehydes characteristically form "addition compounds" with <a href="/wiki/Bisulfite" title="Bisulfite">bisulfites</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCHO + HSO<span class="template-chem2-su"><span>−</span><span>3</span></span> → RCH(OH)SO<span class="template-chem2-su"><span>−</span><span>3</span></span></span></dd></dl> <p>This reaction is used as a test for aldehydes and is useful for separation or purification of aldehydes.<sup id="cite_ref-Fuson_18-1" class="reference"><a href="#cite_note-Fuson-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="More_complex_reactions">More complex reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=19" title="Edit section: More complex reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable" style="background-color: white; float: center; border-collapse: collapse; margin: 0em 1em;"> <tbody><tr> <th>Reaction name</th> <th>Product</th> <th class="unsortable">Comment </th></tr> <tr> <td valign="top"><a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner reduction</a> </td> <td valign="top"><a href="/wiki/Alkane" title="Alkane">Alkane</a> </td> <td>If an aldehyde is converted to a simple hydrazone (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH=NHNH<sub class="template-chem2-sub">2</sub></span>) and this is heated with a base such as KOH, the terminal carbon is fully reduced to a methyl group. The Wolff–Kishner reaction may be performed as a <a href="/wiki/One-pot_synthesis" title="One-pot synthesis">one-pot reaction</a>, giving the overall conversion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH=O → RCH<sub class="template-chem2-sub">3</sub></span>. </td></tr> <tr> <td valign="top"><a href="/wiki/Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a> </td> <td><a href="/wiki/Diol" title="Diol">Diol</a> </td> <td>With reducing agents such as magnesium </td></tr> <tr> <td valign="top"><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkene</a> </td> <td>Reagent: an <a href="/wiki/Ylide" title="Ylide">ylide</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Takai_reaction" class="mw-redirect" title="Takai reaction">Takai reaction</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkene</a> </td> <td>Diorganochromium reagent </td></tr> <tr> <td valign="top"><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reactions</a> </td> <td valign="top"><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a> </td> <td>Phosphine-dibromomethylene reagent </td></tr> <tr> <td valign="top"><a href="/wiki/Ohira%E2%80%93Bestmann_reaction" class="mw-redirect" title="Ohira–Bestmann reaction">Ohira–Bestmann reaction</a> </td> <td valign="top"><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a> </td> <td>Reagent: dimethyl (diazomethyl)phosphonate </td></tr> <tr> <td valign="top"><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a> </td> <td valign="top"><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a> </td> <td>Reagent: a <a href="/wiki/Sulfonium" title="Sulfonium">sulfonium</a> <a href="/wiki/Ylide" title="Ylide">ylide</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Oxo-Diels%E2%80%93Alder_reaction" title="Oxo-Diels–Alder reaction">Oxo-Diels–Alder reaction</a> </td> <td valign="top"><a href="/wiki/Pyran" title="Pyran">Pyran</a> </td> <td>Aldehydes can, typically in the presence of suitable catalysts, serve as partners in <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> reactions. The aldehyde serves as the dienophile component, giving a pyran or related compound. </td></tr> <tr> <td valign="top"><a href="/wiki/Hydroacylation" title="Hydroacylation">Hydroacylation</a> </td> <td valign="top"><a href="/wiki/Ketone" title="Ketone">Ketone</a> </td> <td>In hydroacylation an aldehyde is added over an unsaturated bond to form a <a href="/wiki/Ketone" title="Ketone">ketone</a>. </td></tr> <tr> <td valign="top"><a href="/wiki/Decarbonylation" title="Decarbonylation">Decarbonylation</a> </td> <td valign="top">Alkane </td> <td>Catalysed by transition metals </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Dialdehydes">Dialdehydes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=20" title="Edit section: Dialdehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Dicarbonyl" title="Dicarbonyl">Dicarbonyl</a></div> <p>A <b>dialdehyde</b> is an organic chemical compound with two aldehyde groups. The nomenclature of dialdehydes have the ending <i>-dial</i> or sometimes <i>-dialdehyde</i>. Short aliphatic dialdehydes are sometimes named after the <a href="/wiki/Diacid" class="mw-redirect" title="Diacid">diacid</a> from which they can be derived. An example is <a href="/wiki/Succindialdehyde" class="mw-redirect" title="Succindialdehyde">butanedial</a>, which is also called succinaldehyde (from <a href="/wiki/Succinic_acid" title="Succinic acid">succinic acid</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=21" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some aldehydes are substrates for <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> which metabolize aldehydes in the body. There are <a href="/wiki/Toxicity" title="Toxicity">toxicities</a> associated with some aldehydes that are related to <a href="/wiki/Neurodegeneration" class="mw-redirect" title="Neurodegeneration">neurodegenerative</a> disease, <a href="/wiki/Heart_disease" class="mw-redirect" title="Heart disease">heart disease</a>, and some types of <a href="/wiki/Cancer" title="Cancer">cancer</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Examples_of_aldehydes">Examples of aldehydes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=22" title="Edit section: Examples of aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a> (methanal)</li> <li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a> (ethanal)</li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a> (propanal)</li> <li><a href="/wiki/Butyraldehyde" title="Butyraldehyde">Butyraldehyde</a> (butanal)</li> <li><a href="/wiki/Isovaleraldehyde" title="Isovaleraldehyde">Isovaleraldehyde</a></li> <li><a href="/wiki/Benzaldehyde" title="Benzaldehyde">Benzaldehyde</a> (phenylmethanal)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a></li> <li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a></li> <li><a href="/wiki/Tolualdehyde" class="mw-redirect" title="Tolualdehyde">Tolualdehyde</a></li> <li><a href="/wiki/Furfural" title="Furfural">Furfural</a></li> <li><a href="/wiki/Retinaldehyde" class="mw-redirect" title="Retinaldehyde">Retinaldehyde</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Examples_of_dialdehydes">Examples of dialdehydes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=23" title="Edit section: Examples of dialdehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Glutaraldehyde" title="Glutaraldehyde">Glutaraldehyde</a></li> <li><a href="/wiki/Glyoxal" title="Glyoxal">Glyoxal</a></li> <li><a href="/wiki/Malondialdehyde" title="Malondialdehyde">Malondialdehyde</a></li> <li><a href="/wiki/Phthalaldehyde" title="Phthalaldehyde">Phthalaldehyde</a></li> <li><a href="/wiki/Succindialdehyde" class="mw-redirect" title="Succindialdehyde">Succindialdehyde</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=24" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Of all aldehydes, formaldehyde is produced on the largest scale, about <span class="nowrap"><span data-sort-value="7006600000000000000♠"></span>6<span style="margin-left:.25em;">000</span><span style="margin-left:.25em;">000</span> tons per year</span>. It is mainly used in the production of resins when combined with <a href="/wiki/Urea" title="Urea">urea</a>, <a href="/wiki/Melamine" title="Melamine">melamine</a>, and <a href="/wiki/Phenol" title="Phenol">phenol</a> (e.g., <a href="/wiki/Bakelite" title="Bakelite">Bakelite</a>). It is a precursor to <a href="/wiki/Methylene_diphenyl_diisocyanate" title="Methylene diphenyl diisocyanate">methylene diphenyl diisocyanate</a> ("MDI"), a precursor to <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a>.<sup id="cite_ref-CH2O_7-1" class="reference"><a href="#cite_note-CH2O-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The second main aldehyde is <a href="/wiki/Butyraldehyde" title="Butyraldehyde">butyraldehyde</a>, of which about <span class="nowrap"><span data-sort-value="7006250000000000000♠"></span>2<span style="margin-left:.25em;">500</span><span style="margin-left:.25em;">000</span> tons per year</span> are prepared by <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a>. It is the principal precursor to <a href="/wiki/2-ethylhexanol" class="mw-redirect" title="2-ethylhexanol">2-ethylhexanol</a>, which is used as a <a href="/wiki/Plasticizer" title="Plasticizer">plasticizer</a>.<sup id="cite_ref-aliphald_21-0" class="reference"><a href="#cite_note-aliphald-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Acetaldehyde once was a dominating product, but production levels have declined to less than <span class="nowrap"><span data-sort-value="7006100000000000000♠"></span>1<span style="margin-left:.25em;">000</span><span style="margin-left:.25em;">000</span> tons per year</span> because it mainly served as a precursor to <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, which is now prepared by <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Methanol" title="Methanol">methanol</a>. Many other aldehydes find commercial applications, often as precursors to alcohols, the so-called <a href="/wiki/Oxo_alcohol" title="Oxo alcohol">oxo alcohols</a>, which are used in detergents. Some aldehydes are produced only on a small scale (less than 1000 tons per year) and are used as ingredients in flavours and <a href="/wiki/Perfume" title="Perfume">perfumes</a> such as <a href="/wiki/Chanel_No._5" title="Chanel No. 5">Chanel No. 5</a>. These include <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a> and its derivatives, <a href="/wiki/Citral" title="Citral">citral</a>, and <a href="/wiki/Lilial" title="Lilial">lilial</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=25" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="IUPAC_names_for_aldehydes">IUPAC names for aldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=26" title="Edit section: IUPAC names for aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The common names for aldehydes do not strictly follow official guidelines, such as those recommended by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>, but these rules are useful. IUPAC prescribes the following nomenclature for aldehydes:<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <ol><li>Acyclic <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic</a> aldehydes are named as derivatives of the longest carbon chain containing the aldehyde group. Thus, HCHO is named as a derivative of methane, and <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>CHO</span> is named as a derivative of <a href="/wiki/Butane" title="Butane">butane</a>. The name is formed by changing the suffix <i>-e</i> of the parent <a href="/wiki/Alkane" title="Alkane">alkane</a> to <i>-al</i>, so that HCHO is named <i><a href="/wiki/Methanal" class="mw-redirect" title="Methanal">methanal</a></i>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CHO</span> is named <i><a href="/wiki/Butyraldehyde" title="Butyraldehyde">butanal</a></i>.</li> <li>In other cases, such as when a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CHO</span> group is attached to a ring, the suffix <i>-carbaldehyde</i> may be used. Thus, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">11</sub>CHO</span> is known as <i>cyclohexanecarbaldehyde</i>. If the presence of another functional group demands the use of a suffix, the aldehyde group is named with the prefix <i>formyl-</i>. This prefix is preferred to <i>methanoyl-</i>.</li> <li>If the compound is a natural product or a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, the prefix <i>oxo-</i> may be used to indicate which carbon atom is part of the aldehyde group; for example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CHOCH<sub class="template-chem2-sub">2</sub>COOH</span> is named <i>2-oxoethanoic acid</i>.</li> <li>If replacing the aldehyde group with a <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−COOH</span>) would yield a carboxylic acid with a trivial name, the aldehyde may be named by replacing the suffix <i>-ic acid</i> or <i>-oic acid</i> in this trivial name by <i>-aldehyde</i>.</li></ol> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=27" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word <i>aldehyde</i> was coined by <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a> as a contraction of the Latin <span title="Latin-language text"><i lang="la"><b>al</b>cohol <b>dehyd</b>rogenatus</i></span> (dehydrogenated alcohol).<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> In the past, aldehydes were sometimes named after the corresponding <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>, for example, <i>vinous aldehyde</i> for <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>. (<i>Vinous</i> is from <a href="/wiki/Latin" title="Latin">Latin</a> <span title="Latin-language text"><i lang="la">vinum</i></span> "wine", the traditional source of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, cognate with <i><a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a></i>.) </p><p>The term <i>formyl group</i> is derived from the <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> word <span title="Latin-language text"><i lang="la">formica</i></span> "ant". This word can be recognized in the simplest aldehyde, <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>, and in the simplest carboxylic acid, <a href="/wiki/Formic_acid" title="Formic acid">formic 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=Aldehyde&action=edit&section=28" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Enol" title="Enol">Enol</a></li> <li><a href="/wiki/Pseudoacid" title="Pseudoacid">Pseudoacid</a></li> <li><a href="/wiki/Semialdehyde" title="Semialdehyde">Semialdehyde</a></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aldehyde&action=edit&section=29" 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">IUPAC Gold Book, <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/A00208.html">aldehydes</a>.</span> </li> <li id="cite_note-March-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-March_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-March_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-March_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaul_Patai1966" class="citation book cs1">Saul Patai, ed. (1966). <i>The Carbonyl Group</i>. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons. <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%2F9780470771051">10.1002/9780470771051</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771051" title="Special:BookSources/9780470771051"><bdi>9780470771051</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Carbonyl+Group&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=1966&rft_id=info%3Adoi%2F10.1002%2F9780470771051&rft.isbn=9780470771051&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJacob_Zabicky1970" class="citation book cs1">Jacob Zabicky, ed. (1970). <i>The Carbonyl Group</i>. PATAI'S Chemistry of Functional Groups. Vol. 2. John Wiley & Sons. <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%2F9780470771228">10.1002/9780470771228</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771228" title="Special:BookSources/9780470771228"><bdi>9780470771228</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Carbonyl+Group&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=1970&rft_id=info%3Adoi%2F10.1002%2F9780470771228&rft.isbn=9780470771228&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" 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="CITEREFG._Berthier,_J._Serre1966" class="citation book cs1">G. Berthier, J. Serre (1966). "General and Theoretical Aspects of the Carbonyl Group". In Saul Patai (ed.). <i>The Carbonyl Group</i>. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons. pp. 1–77. <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%2F9780470771051.ch1">10.1002/9780470771051.ch1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771051" title="Special:BookSources/9780470771051"><bdi>9780470771051</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=General+and+Theoretical+Aspects+of+the+Carbonyl+Group&rft.btitle=The+Carbonyl+Group&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pages=1-77&rft.pub=John+Wiley+%26+Sons&rft.date=1966&rft_id=info%3Adoi%2F10.1002%2F9780470771051.ch1&rft.isbn=9780470771051&rft.au=G.+Berthier%2C+J.+Serre&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-Bertleff-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bertleff_5-0">^</a></b></span> <span class="reference-text">Bertleff, W.; Roeper, M. and Sava, X. (2003) "Carbonylation" in <i>Ullmann's Encyclopedia of Industrial Chemistry</i>, Wiley-VCH: Weinheim. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a05_217.pub2">10.1002/14356007.a05_217.pub2</a></span> </li> <li id="cite_note-Ullmann-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTelesHermansFranzSheldon2015" class="citation book cs1">Teles, J. Henrique; Hermans, Ive; Franz, Gerhard; Sheldon, Roger A. (2015). 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(2008) "Aldehydes, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a01_321.pub2">10.1002/14356007.a01_321.pub2</a>.</span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.uwc.edu/dept/chemistry/helpful_files/nomenclature.pdf">Short Summary of IUPAC Nomenclature of Organic Compounds</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20060901144219/http://www.uwc.edu/dept/chemistry/helpful_files/nomenclature.pdf">Archived</a> 2006-09-01 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, web page, University of Wisconsin Colleges, accessed on line August 4, 2007.</span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_449.htm">§R-5.6.1, Aldehydes, thioaldehydes, and their analogues, A Guide to IUPAC Nomenclature of Organic Compounds: recommendations 1993</a>, IUPAC, Commission on Nomenclature of Organic Chemistry, Blackwell Scientific, 1993.</span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_480.htm">§R-5.7.1, Carboxylic acids, A Guide to IUPAC Nomenclature of Organic Compounds: recommendations 1993</a>, IUPAC, Commission on Nomenclature of Organic Chemistry, Blackwell Scientific, 1993.</span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text">Liebig, J. (1835) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=85c5AAAAcAAJ&pg=PA289">"Sur les produits de l'oxidation de l'alcool"</a> (On the products of the oxidation of alcohol), <i>Annales de Chimie et de Physique</i>, <b>59</b>: 289–327. From page 290: "Je le décrirai dans ce mémoire sous le nom <i>d'aldehyde</i> ; ce nom est formé de <i>alcool dehydrogenatus</i>." (I will describe it in this memoir by the name of <i>aldehyde</i>; this name is formed from <i>alcohol dehydrogenatus</i>.)</span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCrosland2004" class="citation cs2">Crosland, Maurice P. (2004), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kwQQaltqByAC&q=alcohol+dehydrogenatus&pg=PA297"><i>Historical Studies in the Language of Chemistry</i></a>, Courier Dover Publications, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780486438023" title="Special:BookSources/9780486438023"><bdi>9780486438023</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Historical+Studies+in+the+Language+of+Chemistry&rft.pub=Courier+Dover+Publications&rft.date=2004&rft.isbn=9780486438023&rft.aulast=Crosland&rft.aufirst=Maurice+P.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkwQQaltqByAC%26q%3Dalcohol%2Bdehydrogenatus%26pg%3DPA297&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span>.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External 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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 class="mw-selflink selflink">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" 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