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Available in 54 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-54" 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">54 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/Karbonielgroep" title="Karbonielgroep – Afrikaans" lang="af" hreflang="af" data-title="Karbonielgroep" 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/%D9%85%D8%AC%D9%85%D9%88%D8%B9%D8%A9_%D9%83%D8%B1%D8%A8%D9%88%D9%86%D9%8A%D9%84" title="مجموعة كربونيل – Arabic" lang="ar" hreflang="ar" data-title="مجموعة كربونيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Karbonil_qrupu" title="Karbonil qrupu – Azerbaijani" lang="az" hreflang="az" data-title="Karbonil qrupu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%95%E0%A6%BE%E0%A6%B0%E0%A7%8D%E0%A6%AC%E0%A6%A8%E0%A6%BF%E0%A6%B2_%E0%A6%AE%E0%A7%82%E0%A6%B2%E0%A6%95" title="কার্বনিল মূলক – Bangla" lang="bn" hreflang="bn" data-title="কার্বনিল মূলক" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B8%D0%BB%D0%BD%D0%B0_%D0%B3%D1%80%D1%83%D0%BF%D0%B0" title="Карбонилна група – Bulgarian" lang="bg" hreflang="bg" data-title="Карбонилна група" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Karbonilna_grupa" title="Karbonilna grupa – Bosnian" lang="bs" hreflang="bs" data-title="Karbonilna grupa" 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/Carbonil" title="Carbonil – Catalan" lang="ca" hreflang="ca" data-title="Carbonil" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Carbonyl" title="Carbonyl – Welsh" lang="cy" hreflang="cy" data-title="Carbonyl" 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/Carbonylgruppe" title="Carbonylgruppe – Danish" lang="da" hreflang="da" data-title="Carbonylgruppe" 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/Carbonylgruppe" title="Carbonylgruppe – German" lang="de" hreflang="de" data-title="Carbonylgruppe" 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/Karbon%C3%BC%C3%BClr%C3%BChm" title="Karbonüülrühm – Estonian" lang="et" hreflang="et" data-title="Karbonüülrühm" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%81%CE%B2%CE%BF%CE%BD%CF%8D%CE%BB%CE%B9%CE%BF" title="Καρβονύλιο – Greek" lang="el" hreflang="el" data-title="Καρβονύλιο" 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/Grupo_carbonilo" title="Grupo carbonilo – Spanish" lang="es" hreflang="es" data-title="Grupo carbonilo" 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/Karbonila_grupo" title="Karbonila grupo – Esperanto" lang="eo" hreflang="eo" data-title="Karbonila grupo" 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/Karbonilo" title="Karbonilo – Basque" lang="eu" hreflang="eu" data-title="Karbonilo" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%D9%86%DB%8C%D9%84" title="کربونیل – Persian" lang="fa" hreflang="fa" data-title="کربونیل" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Groupe_carbonyle" title="Groupe carbonyle – French" lang="fr" hreflang="fr" data-title="Groupe carbonyle" 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/Gr%C3%BApa_carb%C3%B3inile" title="Grúpa carbóinile – Irish" lang="ga" hreflang="ga" data-title="Grúpa carbóinile" 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/Carbonilo" title="Carbonilo – Galician" lang="gl" hreflang="gl" data-title="Carbonilo" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%B4%EB%B3%B4%EB%8B%90%EA%B8%B0" title="카보닐기 – Korean" lang="ko" hreflang="ko" data-title="카보닐기" 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%BF%D5%A1%D6%80%D5%A2%D5%B8%D5%B6%D5%AB%D5%AC%D5%A1%D5%B5%D5%AB%D5%B6_%D5%B4%D5%AB%D5%A1%D6%81%D5%B8%D6%82%D5%A9%D5%B5%D5%B8%D6%82%D5%B6%D5%B6%D5%A5%D6%80" title="Կարբոնիլային միացություններ – Armenian" lang="hy" hreflang="hy" data-title="Կարբոնիլային միացություններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A5%8B%E0%A4%A8%E0%A4%BF%E0%A4%B2_%E0%A4%B8%E0%A4%AE%E0%A5%82%E0%A4%B9" title="कार्बोनिल समूह – Hindi" lang="hi" hreflang="hi" data-title="कार्बोनिल समूह" 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/Karbonilna_skupina" title="Karbonilna skupina – Croatian" lang="hr" hreflang="hr" data-title="Karbonilna skupina" 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/Karbonil" title="Karbonil – Indonesian" lang="id" hreflang="id" data-title="Karbonil" 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/Carbonile" title="Carbonile – Italian" lang="it" hreflang="it" data-title="Carbonile" 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%A7%D7%A8%D7%91%D7%95%D7%A0%D7%99%D7%9C" title="קרבוניל – Hebrew" lang="he" hreflang="he" data-title="קרבוניל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Karbonilgrupa" title="Karbonilgrupa – Latvian" lang="lv" hreflang="lv" data-title="Karbonilgrupa" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Karbonilcsoport" title="Karbonilcsoport – Hungarian" lang="hu" hreflang="hu" data-title="Karbonilcsoport" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B8%D0%BB%D0%BD%D0%B0_%D0%B3%D1%80%D1%83%D0%BF%D0%B0" title="Карбонилна група – Macedonian" lang="mk" hreflang="mk" data-title="Карбонилна група" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%95%E0%B4%BE%E0%B5%BC%E0%B4%AC%E0%B5%8B%E0%B4%A3%E0%B4%BF%E0%B5%BD_%E0%B4%97%E0%B5%8D%E0%B4%B0%E0%B5%82%E0%B4%AA%E0%B5%8D%E0%B4%AA%E0%B5%8D" title="കാർബോണിൽ ഗ്രൂപ്പ് – Malayalam" lang="ml" hreflang="ml" data-title="കാർബോണിൽ ഗ്രൂപ്പ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Kumpulan_karbonil" title="Kumpulan karbonil – Malay" lang="ms" hreflang="ms" data-title="Kumpulan karbonil" 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/Carbonylgroep" title="Carbonylgroep – Dutch" lang="nl" hreflang="nl" data-title="Carbonylgroep" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%AB%E3%83%9C%E3%83%8B%E3%83%AB%E5%9F%BA" title="カルボニル基 – Japanese" lang="ja" hreflang="ja" data-title="カルボニル基" 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/Karbonyl" title="Karbonyl – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Karbonyl" 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/Karbonyl" title="Karbonyl – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Karbonyl" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%95%E0%A8%BE%E0%A8%B0%E0%A8%AC%E0%A9%8B%E0%A8%A8%E0%A8%BF%E0%A8%B2" title="ਕਾਰਬੋਨਿਲ – Punjabi" lang="pa" hreflang="pa" data-title="ਕਾਰਬੋਨਿਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Grupa_karbonylowa" title="Grupa karbonylowa – Polish" lang="pl" hreflang="pl" data-title="Grupa karbonylowa" 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/Carbonila" title="Carbonila – Portuguese" lang="pt" hreflang="pt" data-title="Carbonila" 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/Carbonil" title="Carbonil – Romanian" lang="ro" hreflang="ro" data-title="Carbonil" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%B3%D1%80%D1%83%D0%BF%D0%BF%D0%B0" title="Карбонильная группа – Russian" lang="ru" hreflang="ru" data-title="Карбонильная группа" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Derivatet_Karbonilike" title="Derivatet Karbonilike – Albanian" lang="sq" hreflang="sq" data-title="Derivatet Karbonilike" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carbonyl" title="Carbonyl – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carbonyl" 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/Karbonylov%C3%A1_skupina" title="Karbonylová skupina – Slovak" lang="sk" hreflang="sk" data-title="Karbonylová skupina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Karbonilna_grupa" title="Karbonilna grupa – Serbian" lang="sr" hreflang="sr" data-title="Karbonilna grupa" 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/Karbonil" title="Karbonil – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Karbonil" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karbonyyliryhm%C3%A4" title="Karbonyyliryhmä – Finnish" lang="fi" hreflang="fi" data-title="Karbonyyliryhmä" 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/Karbonylgrupp" title="Karbonylgrupp – Swedish" lang="sv" hreflang="sv" data-title="Karbonylgrupp" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%AA%E0%AE%A9%E0%AF%88%E0%AE%B2%E0%AF%8D" title="கார்பனைல் – Tamil" lang="ta" hreflang="ta" data-title="கார்பனைல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Karbonil_grubu" title="Karbonil grubu – Turkish" lang="tr" hreflang="tr" data-title="Karbonil grubu" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D1%96%D0%BB%D1%8C%D0%BD%D0%B0_%D0%B3%D1%80%D1%83%D0%BF%D0%B0" title="Карбонільна група – Ukrainian" lang="uk" hreflang="uk" data-title="Карбонільна група" 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/Carbonyl" title="Carbonyl – Vietnamese" lang="vi" hreflang="vi" data-title="Carbonyl" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%BE%B0%E5%9F%BA" title="羰基 – Wu" lang="wuu" 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id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Functional group (C=O)</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">For carboxyl as a ligand, see <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">Metal carbonyl</a>. For the web browser, see <a href="/wiki/Carbonyl_(web_browser)" class="mw-redirect" title="Carbonyl (web browser)">Carbonyl (web browser)</a>.</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ketone-general.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/220px-Ketone-general.svg.png" decoding="async" width="220" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/330px-Ketone-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/440px-Ketone-general.svg.png 2x" data-file-width="760" data-file-height="665" /></a><figcaption>A ketone compound containing a carbonyl group (C=O)</figcaption></figure> <p>For <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>carbonyl group</b> is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C=O</span>, composed of a <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atom</a> <a href="/wiki/Double_bond" title="Double bond">double-bonded</a> to an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom, and it is <a href="/wiki/Divalent" class="mw-redirect" title="Divalent">divalent</a> at the C atom. It is common to several classes of organic compounds (such as <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a>, <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">ketones</a> and <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">carboxylic acids</a>), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.<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> </p><p>The term carbonyl can also refer to <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> as a <a href="/wiki/Ligand" title="Ligand">ligand</a> in an <a href="/wiki/Inorganic" class="mw-redirect" title="Inorganic">inorganic</a> or <a href="/wiki/Organometallic" class="mw-redirect" title="Organometallic">organometallic</a> complex (a <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyl</a>, e.g. <a href="/wiki/Nickel_carbonyl" class="mw-redirect" title="Nickel carbonyl">nickel carbonyl</a>). </p><p>The remainder of this article concerns itself with the organic chemistry definition of carbonyl, such that carbon and oxygen share a double bond. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Carbonyl_compounds">Carbonyl compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbonyl_group&action=edit&section=1" title="Edit section: Carbonyl compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/%CE%91,%CE%B2-Unsaturated_carbonyl_compound" title="Α,β-Unsaturated carbonyl compound">α,β-Unsaturated carbonyl compound</a></div> <p>In organic chemistry, a carbonyl group characterizes the following types of compounds: </p> <table class="wikitable"> <tbody><tr> <th align="center"><b>Compound</b> </th> <td><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a></td> <td><a href="/wiki/Ketone" title="Ketone">Ketone</a></td> <td><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a></td> <td><a href="/wiki/Ester" title="Ester">Carboxylate ester</a></td> <td><a href="/wiki/Amide" title="Amide">Amide</a> </td></tr> <tr> <th align="center"><b>Structure</b> </th> <td><span typeof="mw:File"><a href="/wiki/File:Aldehyd_-_Aldehyde.svg" class="mw-file-description" title="Aldehyde"><img alt="Aldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aldehyd_-_Aldehyde.svg/60px-Aldehyd_-_Aldehyde.svg.png" decoding="async" width="60" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aldehyd_-_Aldehyde.svg/90px-Aldehyd_-_Aldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Aldehyd_-_Aldehyde.svg/120px-Aldehyd_-_Aldehyde.svg.png 2x" data-file-width="83" data-file-height="77" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Ketone-general.svg" class="mw-file-description" title="Ketone"><img alt="Ketone" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/60px-Ketone-general.svg.png" decoding="async" width="60" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/90px-Ketone-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Ketone-general.svg/120px-Ketone-general.svg.png 2x" data-file-width="760" data-file-height="665" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Carboxylic-acid.svg" class="mw-file-description" title="Carboxylic acid"><img alt="Carboxylic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/60px-Carboxylic-acid.svg.png" decoding="async" width="60" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/90px-Carboxylic-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/120px-Carboxylic-acid.svg.png 2x" data-file-width="927" data-file-height="743" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Ester.svg" class="mw-file-description" title="Ester"><img alt="Ester" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ester.svg/60px-Ester.svg.png" decoding="async" width="60" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ester.svg/90px-Ester.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ester.svg/120px-Ester.svg.png 2x" data-file-width="440" data-file-height="325" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Amide-(tertiary).svg" class="mw-file-description" title="Amide"><img alt="Amide" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Amide-%28tertiary%29.svg/80px-Amide-%28tertiary%29.svg.png" decoding="async" width="80" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Amide-%28tertiary%29.svg/120px-Amide-%28tertiary%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Amide-%28tertiary%29.svg/160px-Amide-%28tertiary%29.svg.png 2x" data-file-width="512" data-file-height="473" /></a></span> </td></tr> <tr> <th align="center"><b>General formula</b> </th> <td>RCHO</td> <td>RCOR'</td> <td>RCOOH</td> <td>RCOOR'</td> <td>RCONR'R'' </td></tr></tbody></table> <table class="wikitable"> <tbody><tr> <th align="center"><b>Compound</b> </th> <td><a href="/wiki/Alpha-beta_Unsaturated_carbonyl_compounds#Enones" class="mw-redirect" title="Alpha-beta Unsaturated carbonyl compounds">Enone</a></td> <td><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a></td> <td><a href="/wiki/Acid_anhydride" title="Acid anhydride">Acid anhydride</a></td> <td><a href="/wiki/Imide" title="Imide">Imide</a> </td></tr> <tr> <th align="center"><b>Structure</b> </th> <td><span typeof="mw:File"><a href="/wiki/File:Enone-general.png" class="mw-file-description" title="Enone"><img alt="Enone" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Enone-general.png/90px-Enone-general.png" decoding="async" width="90" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Enone-general.png/135px-Enone-general.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Enone-general.png/180px-Enone-general.png 2x" data-file-width="1383" data-file-height="1044" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Acyl-halide.svg" class="mw-file-description" title="Acyl chloride"><img alt="Acyl chloride" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/60px-Acyl-halide.svg.png" decoding="async" width="60" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/90px-Acyl-halide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/120px-Acyl-halide.svg.png 2x" data-file-width="512" data-file-height="476" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Carboxylic-acid-anhydride.png" class="mw-file-description" title="Acid anhydride"><img alt="Acid anhydride" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Carboxylic-acid-anhydride.png/95px-Carboxylic-acid-anhydride.png" decoding="async" width="95" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Carboxylic-acid-anhydride.png/143px-Carboxylic-acid-anhydride.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Carboxylic-acid-anhydride.png/190px-Carboxylic-acid-anhydride.png 2x" data-file-width="1347" data-file-height="744" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Imide-general.png" class="mw-file-description" title="Imide"><img alt="Imide" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Imide-general.png/95px-Imide-general.png" decoding="async" width="95" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Imide-general.png/143px-Imide-general.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Imide-general.png/190px-Imide-general.png 2x" data-file-width="1320" data-file-height="1044" /></a></span> </td></tr> <tr> <th align="center"><b>General formula</b> </th> <td>RC(O)C(R')CR''R'''</td> <td>RCOX</td> <td>(RCO)<sub>2</sub>O</td> <td>RC(O)N(R')C(O)R'' </td></tr></tbody></table> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Carbon_dioxide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Carbon_dioxide.svg/180px-Carbon_dioxide.svg.png" decoding="async" width="180" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Carbon_dioxide.svg/270px-Carbon_dioxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Carbon_dioxide.svg/360px-Carbon_dioxide.svg.png 2x" data-file-width="320" data-file-height="107" /></a><figcaption>Carbon dioxide</figcaption></figure> <p>Other organic carbonyls are <a href="/wiki/Urea" title="Urea">urea</a> and the <a href="/wiki/Carbamate" title="Carbamate">carbamates</a>, the derivatives of <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> <a href="/wiki/Chloroformate" title="Chloroformate">chloroformates</a> and <a href="/wiki/Phosgene" title="Phosgene">phosgene</a>, <a href="/wiki/Carbonate_ester" title="Carbonate ester">carbonate esters</a>, <a href="/wiki/Thioester" title="Thioester">thioesters</a>, <a href="/wiki/Lactone" title="Lactone">lactones</a>, <a href="/wiki/Lactam" title="Lactam">lactams</a>, <a href="/wiki/Hydroxamic_acid" title="Hydroxamic acid">hydroxamates</a>, and <a href="/wiki/Isocyanate" title="Isocyanate">isocyanates</a>. Examples of inorganic carbonyl compounds are <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">carbonyl sulfide</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2021)">citation needed</span></a></i>]</sup> </p><p>A special group of carbonyl compounds are <a href="/wiki/Dicarbonyl" title="Dicarbonyl">dicarbonyl</a> compounds, which can exhibit special properties. </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_reactivity">Structure and reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbonyl_group&action=edit&section=2" title="Edit section: Structure and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For organic compounds, the length of the C-O bond does not vary widely from 120 <a href="/wiki/Picometer" class="mw-redirect" title="Picometer">picometers</a>. Inorganic carbonyls have shorter C-O distances: <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a>, 113; <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a>, 116; and <a href="/wiki/Phosgene" title="Phosgene">COCl<sub>2</sub></a>, 116 pm.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The carbonyl carbon is typically <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a>. A qualitative order of electrophilicity is RCHO (aldehydes) > R<sub>2</sub>CO (ketones) > RCO<sub>2</sub>R' (esters) > RCONH<sub>2</sub> (amides). A variety of nucleophiles attack, breaking the carbon-oxygen <a href="/wiki/Pi_bond" title="Pi bond">double bond</a>. </p><p>Interactions between carbonyl groups and other substituents were found in a study of <a href="/wiki/Collagen" title="Collagen">collagen</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Substituents can affect carbonyl groups by addition or subtraction of electron density by means of a <a href="/wiki/Sigma_bond" title="Sigma bond">sigma bond</a>.<sup id="cite_ref-:0_4-0" class="reference"><a href="#cite_note-:0-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Δ<i>H</i>σ values are much greater when the substituents on the carbonyl group are more electronegative than carbon.<sup id="cite_ref-:0_4-1" class="reference"><a href="#cite_note-:0-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Carbonylgruppe.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Carbonylgruppe.svg/220px-Carbonylgruppe.svg.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Carbonylgruppe.svg/330px-Carbonylgruppe.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Carbonylgruppe.svg/440px-Carbonylgruppe.svg.png 2x" data-file-width="255" data-file-height="149" /></a><figcaption>A carbonyl compound</figcaption></figure> <p>The polarity of C=O bond also enhances the acidity of any adjacent C-H bonds. Due to the positive charge on carbon and the negative charge on oxygen, carbonyl groups are subject to additions and/or nucleophilic attacks. A variety of nucleophiles attack, breaking the carbon-oxygen <a href="/wiki/Pi_bond" title="Pi bond">double bond</a>, and leading to <a href="/wiki/Addition%E2%80%93elimination_reaction" title="Addition–elimination reaction">addition-elimination reactions</a>. Nucleophiliic reactivity is often proportional to the basicity of the nucleophile and as nucleophilicity increases, the stability within a carbonyl compound decreases.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> values of <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> and <a href="/wiki/Acetone" title="Acetone">acetone</a> are 16.7 and 19 respectively,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Spectroscopy">Spectroscopy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbonyl_group&action=edit&section=3" title="Edit section: Spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">Infrared spectroscopy</a>: the C=O double bond absorbs <a href="/wiki/Infrared" title="Infrared">infrared</a> light at <a href="/wiki/Wavenumber" title="Wavenumber">wavenumbers</a> between approximately 1600–1900 cm<sup>−1</sup>(5263 nm to 6250 nm). The exact location of the absorption is well understood with respect to the geometry of the molecule. This absorption is known as the "carbonyl stretch" when displayed on an infrared absorption spectrum.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In addition, the ultraviolet-visible spectra of propanone in water gives an absorption of carbonyl at 257 nm.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">Nuclear magnetic resonance</a>: the C=O double-bond exhibits different resonances depending on surrounding atoms, generally a downfield shift. The <sup>13</sup>C NMR of a carbonyl carbon is in the range of 160–220 ppm.<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></li></ul> <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=Carbonyl_group&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">Carbon–oxygen bond</a></li> <li><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic chemistry</a></li> <li><a href="/wiki/Functional_group" title="Functional group">Functional group</a></li> <li><a href="/wiki/Bridging_carbonyl" class="mw-redirect" title="Bridging carbonyl">Bridging carbonyl</a></li> <li><a href="/wiki/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</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=Carbonyl_group&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration 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="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%3ACarbonyl+group" 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>. 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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%3ACarbonyl+group" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFG._Berthier,_J._Serre1966" class="citation book cs1">G. 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(1999-11-01). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/ar990008h">"The Interaction of Carbonyl Groups with Substituents"</a>. <i>Accounts of Chemical Research</i>. <b>32</b> (11): 922–929. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far990008h">10.1021/ar990008h</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0001-4842">0001-4842</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Accounts+of+Chemical+Research&rft.atitle=The+Interaction+of+Carbonyl+Groups+with+Substituents&rft.volume=32&rft.issue=11&rft.pages=922-929&rft.date=1999-11-01&rft_id=info%3Adoi%2F10.1021%2Far990008h&rft.issn=0001-4842&rft.aulast=Wiberg&rft.aufirst=Kenneth+B.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Far990008h&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbonyl+group" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLienhardJencks1966" class="citation journal cs1">Lienhard, Gustav E.; Jencks, William P. (September 1966). <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021/ja00969a017">"Thiol Addition to the Carbonyl Group. Equilibria and Kinetics<sup>1</sup>"</a>. <i>Journal of the American Chemical Society</i>. <b>88</b> (17): 3982–3995. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00969a017">10.1021/ja00969a017</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5915153">5915153</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Thiol+Addition+to+the+Carbonyl+Group.+Equilibria+and+Kinetics%3Csup%3E1%3C%2Fsup%3E&rft.volume=88&rft.issue=17&rft.pages=3982-3995&rft.date=1966-09&rft.issn=0002-7863&rft_id=info%3Apmid%2F5915153&rft_id=info%3Adoi%2F10.1021%2Fja00969a017&rft.aulast=Lienhard&rft.aufirst=Gustav+E.&rft.au=Jencks%2C+William+P.&rft_id=http%3A%2F%2Fdx.doi.org%2F10.1021%2Fja00969a017&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbonyl+group" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">Ouellette, R.J. and Rawn, J.D. "Organic Chemistry" 1st Ed. Prentice-Hall, Inc., 1996: New Jersey. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-02-390171-3" title="Special:BookSources/0-02-390171-3">0-02-390171-3</a></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Mayo D.W., Miller F.A and Hannah R.W “Course Notes On The Interpretation of Infrared and Raman Spectra” 1st Ed. John Wiley & Sons Inc, 2004: New Jersey. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-24823-1" title="Special:BookSources/0-471-24823-1">0-471-24823-1</a>.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150824053622/http://media.rsc.org/Modern%20chemical%20techniques/MCT4%20UV%20and%20visible%20spec.pdf">"Archived copy"</a> <span class="cs1-format">(PDF)</span>. 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Retrieved <span class="nowrap">2015-07-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Archived+copy&rft_id=http%3A%2F%2Fmedia.rsc.org%2FModern%2520chemical%2520techniques%2FMCT4%2520UV%2520and%2520visible%2520spec.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbonyl+group" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_web" title="Template:Cite web">cite web</a>}}</code>: CS1 maint: archived copy as title (<a href="/wiki/Category:CS1_maint:_archived_copy_as_title" title="Category:CS1 maint: archived copy as title">link</a>)</span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20240106080835/https://organicchemistrydata.org/hansreich/resources/nmr/?index=nmr_index%2F13C_shift">"NMR Spectroscopy. 13C NMR"</a>. <i>organicchemistrydata.org</i>. 20 October 2021. Archived from <a rel="nofollow" class="external text" href="https://organicchemistrydata.org/hansreich/resources/nmr/?index=nmr_index%2F13C_shift">the original</a> on 6 January 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">6 January</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=organicchemistrydata.org&rft.atitle=NMR+Spectroscopy.+13C+NMR&rft.date=2021-10-20&rft_id=https%3A%2F%2Forganicchemistrydata.org%2Fhansreich%2Fresources%2Fnmr%2F%3Findex%3Dnmr_index%252F13C_shift&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbonyl+group" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbonyl_group&action=edit&section=6" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Carbonyl_group" class="extiw" title="commons:Category:Carbonyl group">Carbonyl group</a></span>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></span></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Carbonyl_group" class="extiw" title="q:Special:Search/Carbonyl group">Carbonyl group</a></b></i>.</div></div> </div> <ul><li>L.G. Wade, Jr. <i>Organic Chemistry, 5th ed.</i> <a href="/wiki/Prentice_Hall" title="Prentice Hall">Prentice Hall</a>, 2002. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-13-033832-X" title="Special:BookSources/0-13-033832-X">0-13-033832-X</a></li> <li>The <a href="/wiki/Frostburg_State_University" title="Frostburg State University">Frostburg State University</a> Chemistry Department. <a rel="nofollow" class="external text" href="http://www.chemhelper.com/">Organic Chemistry Help</a> (2000).</li> <li>Advanced Chemistry Development, Inc. <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature">IUPAC Nomenclature of Organic Chemistry</a> (1997).</li> <li>William Reusch. tara <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071029211245/http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm">VirtualText of Organic Chemistry</a> (2004).</li> <li>Purdue Chemistry Department <a rel="nofollow" class="external autonumber" href="http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/carbonyl.html">[1]</a> (retrieved Sep 2006). Includes water solubility data.</li> <li>William Reusch. (2004) <a rel="nofollow" class="external text" href="https://web.archive.org/web/20020917024512/http://www.cem.msu.edu/~reusch/VirtualText/aldket1.htm">Aldehydes and Ketones</a> Retrieved 23 May 2005.</li> <li>ILPI. (2005) <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150402093646/http://www.ilpi.com/msds/ref/anhydride.html">The MSDS Hyperglossary- Anhydride</a>.</li></ul> <div style="clear:both;" class=""></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist 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"}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" 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