CINXE.COM

<!DOCTYPE html> <html class="client-nojs skin-theme-clientpref-day mf-expand-sections-clientpref-0 mf-font-size-clientpref-small mw-mf-amc-clientpref-0" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Aldehyde - Wikipedia</title> <script>(function(){var className="client-js skin-theme-clientpref-day mf-expand-sections-clientpref-0 mf-font-size-clientpref-small mw-mf-amc-clientpref-0";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy","wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"b17af11b-905c-4e19-b7f8-8a18ca5f4b0e","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Aldehyde","wgTitle":"Aldehyde","wgCurRevisionId":1256928529,"wgRevisionId":1256928529,"wgArticleId":37329,"wgIsArticle": true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Aldehyde","wgRelevantArticleId":37329,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFMode":"stable","wgMFAmc":false,"wgMFAmcOutreachActive":false,"wgMFAmcOutreachUserEligible":false,"wgMFLazyLoadImages":true,"wgMFEditNoticesFeatureConflict":false,"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgMFIsSupportedEditRequest":true,"wgMFScriptPath":"", "wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":30000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":true,"wgEditSubmitButtonLabelPublish":true,"wgSectionTranslationMissingLanguages":[{"lang":"ace","autonym":"Acèh","dir":"ltr"},{"lang":"ady","autonym":"адыгабзэ","dir":"ltr"},{"lang":"alt","autonym":"алтай тил","dir":"ltr"},{"lang":"am","autonym":"አማርኛ","dir":"ltr"},{"lang":"ami","autonym":"Pangcah","dir":"ltr"},{"lang":"an","autonym":"aragonés","dir":"ltr"},{"lang":"ang","autonym":"Ænglisc","dir":"ltr"},{"lang":"ann","autonym":"Obolo","dir":"ltr"},{"lang":"anp","autonym":"अंगिका","dir":"ltr"},{"lang":"ary","autonym":"الدارجة","dir":"rtl"},{"lang":"arz","autonym":"مصرى","dir":"rtl"},{"lang":"as","autonym":"অসমীয়া","dir":"ltr"},{"lang":"av","autonym":"авар","dir":"ltr"},{"lang":"avk","autonym":"Kotava","dir":"ltr"},{"lang":"awa","autonym":"अवधी","dir":"ltr"},{"lang":"ay","autonym": "Aymar aru","dir":"ltr"},{"lang":"ba","autonym":"башҡортса","dir":"ltr"},{"lang":"ban","autonym":"Basa Bali","dir":"ltr"},{"lang":"bar","autonym":"Boarisch","dir":"ltr"},{"lang":"bbc","autonym":"Batak Toba","dir":"ltr"},{"lang":"bdr","autonym":"Bajau Sama","dir":"ltr"},{"lang":"bew","autonym":"Betawi","dir":"ltr"},{"lang":"bho","autonym":"भोजपुरी","dir":"ltr"},{"lang":"bi","autonym":"Bislama","dir":"ltr"},{"lang":"bjn","autonym":"Banjar","dir":"ltr"},{"lang":"blk","autonym":"ပအိုဝ်ႏဘာႏသာႏ","dir":"ltr"},{"lang":"bm","autonym":"bamanankan","dir":"ltr"},{"lang":"bpy","autonym":"বিষ্ণুপ্রিয়া মণিপুরী","dir":"ltr"},{"lang":"br","autonym":"brezhoneg","dir":"ltr"},{"lang":"btm","autonym":"Batak Mandailing","dir":"ltr"},{"lang":"bug","autonym":"Basa Ugi","dir":"ltr"},{"lang":"cdo","autonym":"閩東語 / Mìng-dĕ̤ng-ngṳ̄","dir":"ltr"},{"lang":"ce","autonym":"нохчийн","dir":"ltr"},{"lang":"ceb", "autonym":"Cebuano","dir":"ltr"},{"lang":"ch","autonym":"Chamoru","dir":"ltr"},{"lang":"chr","autonym":"ᏣᎳᎩ","dir":"ltr"},{"lang":"co","autonym":"corsu","dir":"ltr"},{"lang":"cr","autonym":"Nēhiyawēwin / ᓀᐦᐃᔭᐍᐏᐣ","dir":"ltr"},{"lang":"crh","autonym":"qırımtatarca","dir":"ltr"},{"lang":"cu","autonym":"словѣньскъ / ⰔⰎⰑⰂⰡⰐⰠⰔⰍⰟ","dir":"ltr"},{"lang":"dag","autonym":"dagbanli","dir":"ltr"},{"lang":"dga","autonym":"Dagaare","dir":"ltr"},{"lang":"din","autonym":"Thuɔŋjäŋ","dir":"ltr"},{"lang":"diq","autonym":"Zazaki","dir":"ltr"},{"lang":"dsb","autonym":"dolnoserbski","dir":"ltr"},{"lang":"dtp","autonym":"Kadazandusun","dir":"ltr"},{"lang":"dv","autonym":"ދިވެހިބަސް","dir":"rtl"},{"lang":"dz","autonym":"ཇོང་ཁ","dir":"ltr"},{"lang":"ee","autonym":"eʋegbe","dir":"ltr"},{"lang":"eml","autonym":"emiliàn e rumagnòl","dir":"ltr"},{"lang":"fat","autonym":"mfantse","dir":"ltr"},{"lang":"ff","autonym":"Fulfulde","dir": "ltr"},{"lang":"fj","autonym":"Na Vosa Vakaviti","dir":"ltr"},{"lang":"fon","autonym":"fɔ̀ngbè","dir":"ltr"},{"lang":"frp","autonym":"arpetan","dir":"ltr"},{"lang":"frr","autonym":"Nordfriisk","dir":"ltr"},{"lang":"fur","autonym":"furlan","dir":"ltr"},{"lang":"fy","autonym":"Frysk","dir":"ltr"},{"lang":"gag","autonym":"Gagauz","dir":"ltr"},{"lang":"gan","autonym":"贛語","dir":"ltr"},{"lang":"gcr","autonym":"kriyòl gwiyannen","dir":"ltr"},{"lang":"glk","autonym":"گیلکی","dir":"rtl"},{"lang":"gn","autonym":"Avañe'ẽ","dir":"ltr"},{"lang":"gom","autonym":"गोंयची कोंकणी / Gõychi Konknni","dir":"ltr"},{"lang":"gor","autonym":"Bahasa Hulontalo","dir":"ltr"},{"lang":"gpe","autonym":"Ghanaian Pidgin","dir":"ltr"},{"lang":"gu","autonym":"ગુજરાતી","dir":"ltr"},{"lang":"guc","autonym":"wayuunaiki","dir":"ltr"},{"lang":"gur","autonym":"farefare","dir":"ltr"},{"lang":"guw","autonym":"gungbe","dir":"ltr"},{"lang":"gv","autonym":"Gaelg","dir":"ltr"} ,{"lang":"ha","autonym":"Hausa","dir":"ltr"},{"lang":"hak","autonym":"客家語 / Hak-kâ-ngî","dir":"ltr"},{"lang":"haw","autonym":"Hawaiʻi","dir":"ltr"},{"lang":"hif","autonym":"Fiji Hindi","dir":"ltr"},{"lang":"hsb","autonym":"hornjoserbsce","dir":"ltr"},{"lang":"ht","autonym":"Kreyòl ayisyen","dir":"ltr"},{"lang":"hyw","autonym":"Արեւմտահայերէն","dir":"ltr"},{"lang":"ia","autonym":"interlingua","dir":"ltr"},{"lang":"iba","autonym":"Jaku Iban","dir":"ltr"},{"lang":"ie","autonym":"Interlingue","dir":"ltr"},{"lang":"ig","autonym":"Igbo","dir":"ltr"},{"lang":"igl","autonym":"Igala","dir":"ltr"},{"lang":"ilo","autonym":"Ilokano","dir":"ltr"},{"lang":"io","autonym":"Ido","dir":"ltr"},{"lang":"is","autonym":"íslenska","dir":"ltr"},{"lang":"iu","autonym":"ᐃᓄᒃᑎᑐᑦ / inuktitut","dir":"ltr"},{"lang":"jam","autonym":"Patois","dir":"ltr"},{"lang":"jv","autonym":"Jawa","dir":"ltr"},{"lang":"kaa","autonym":"Qaraqalpaqsha","dir":"ltr"},{"lang":"kab","autonym": "Taqbaylit","dir":"ltr"},{"lang":"kbd","autonym":"адыгэбзэ","dir":"ltr"},{"lang":"kbp","autonym":"Kabɩyɛ","dir":"ltr"},{"lang":"kcg","autonym":"Tyap","dir":"ltr"},{"lang":"kg","autonym":"Kongo","dir":"ltr"},{"lang":"kge","autonym":"Kumoring","dir":"ltr"},{"lang":"ki","autonym":"Gĩkũyũ","dir":"ltr"},{"lang":"kl","autonym":"kalaallisut","dir":"ltr"},{"lang":"km","autonym":"ភាសាខ្មែរ","dir":"ltr"},{"lang":"koi","autonym":"перем коми","dir":"ltr"},{"lang":"krc","autonym":"къарачай-малкъар","dir":"ltr"},{"lang":"ks","autonym":"कॉशुर / کٲشُر","dir":"rtl"},{"lang":"ku","autonym":"kurdî","dir":"ltr"},{"lang":"kus","autonym":"Kʋsaal","dir":"ltr"},{"lang":"kv","autonym":"коми","dir":"ltr"},{"lang":"kw","autonym":"kernowek","dir":"ltr"},{"lang":"lad","autonym":"Ladino","dir":"ltr"},{"lang":"lb","autonym":"Lëtzebuergesch","dir":"ltr"},{"lang":"lez","autonym":"лезги","dir":"ltr"},{"lang":"lg","autonym":"Luganda","dir" :"ltr"},{"lang":"li","autonym":"Limburgs","dir":"ltr"},{"lang":"lij","autonym":"Ligure","dir":"ltr"},{"lang":"lld","autonym":"Ladin","dir":"ltr"},{"lang":"lmo","autonym":"lombard","dir":"ltr"},{"lang":"ln","autonym":"lingála","dir":"ltr"},{"lang":"lo","autonym":"ລາວ","dir":"ltr"},{"lang":"ltg","autonym":"latgaļu","dir":"ltr"},{"lang":"mad","autonym":"Madhurâ","dir":"ltr"},{"lang":"mai","autonym":"मैथिली","dir":"ltr"},{"lang":"map-bms","autonym":"Basa Banyumasan","dir":"ltr"},{"lang":"mdf","autonym":"мокшень","dir":"ltr"},{"lang":"mg","autonym":"Malagasy","dir":"ltr"},{"lang":"mhr","autonym":"олык марий","dir":"ltr"},{"lang":"mi","autonym":"Māori","dir":"ltr"},{"lang":"min","autonym":"Minangkabau","dir":"ltr"},{"lang":"ml","autonym":"മലയാളം","dir":"ltr"},{"lang":"mn","autonym":"монгол","dir":"ltr"},{"lang":"mni","autonym":"ꯃꯤꯇꯩ ꯂꯣꯟ","dir":"ltr"},{"lang":"mnw","autonym":"ဘာသာမန်","dir":"ltr"},{"lang": "mos","autonym":"moore","dir":"ltr"},{"lang":"mr","autonym":"मराठी","dir":"ltr"},{"lang":"mrj","autonym":"кырык мары","dir":"ltr"},{"lang":"mt","autonym":"Malti","dir":"ltr"},{"lang":"mwl","autonym":"Mirandés","dir":"ltr"},{"lang":"my","autonym":"မြန်မာဘာသာ","dir":"ltr"},{"lang":"myv","autonym":"эрзянь","dir":"ltr"},{"lang":"nah","autonym":"Nāhuatl","dir":"ltr"},{"lang":"nan","autonym":"閩南語 / Bân-lâm-gú","dir":"ltr"},{"lang":"nap","autonym":"Napulitano","dir":"ltr"},{"lang":"nb","autonym":"norsk bokmål","dir":"ltr"},{"lang":"nds-nl","autonym":"Nedersaksies","dir":"ltr"},{"lang":"ne","autonym":"नेपाली","dir":"ltr"},{"lang":"new","autonym":"नेपाल भाषा","dir":"ltr"},{"lang":"nia","autonym":"Li Niha","dir":"ltr"},{"lang":"nqo","autonym":"ߒߞߏ","dir":"rtl"},{"lang":"nr","autonym":"isiNdebele seSewula","dir":"ltr"},{"lang":"nso","autonym":"Sesotho sa Leboa","dir":"ltr"},{"lang":"ny","autonym":"Chi-Chewa" ,"dir":"ltr"},{"lang":"om","autonym":"Oromoo","dir":"ltr"},{"lang":"or","autonym":"ଓଡ଼ିଆ","dir":"ltr"},{"lang":"os","autonym":"ирон","dir":"ltr"},{"lang":"pag","autonym":"Pangasinan","dir":"ltr"},{"lang":"pam","autonym":"Kapampangan","dir":"ltr"},{"lang":"pap","autonym":"Papiamentu","dir":"ltr"},{"lang":"pcd","autonym":"Picard","dir":"ltr"},{"lang":"pcm","autonym":"Naijá","dir":"ltr"},{"lang":"pdc","autonym":"Deitsch","dir":"ltr"},{"lang":"pms","autonym":"Piemontèis","dir":"ltr"},{"lang":"pwn","autonym":"pinayuanan","dir":"ltr"},{"lang":"qu","autonym":"Runa Simi","dir":"ltr"},{"lang":"rm","autonym":"rumantsch","dir":"ltr"},{"lang":"rn","autonym":"ikirundi","dir":"ltr"},{"lang":"rsk","autonym":"руски","dir":"ltr"},{"lang":"rue","autonym":"русиньскый","dir":"ltr"},{"lang":"rup","autonym":"armãneashti","dir":"ltr"},{"lang":"rw","autonym":"Ikinyarwanda","dir":"ltr"},{"lang":"sa","autonym":"संस्कृतम्","dir":"ltr"},{"lang":"sah","autonym": "саха тыла","dir":"ltr"},{"lang":"sat","autonym":"ᱥᱟᱱᱛᱟᱲᱤ","dir":"ltr"},{"lang":"sc","autonym":"sardu","dir":"ltr"},{"lang":"scn","autonym":"sicilianu","dir":"ltr"},{"lang":"sco","autonym":"Scots","dir":"ltr"},{"lang":"sd","autonym":"سنڌي","dir":"rtl"},{"lang":"se","autonym":"davvisámegiella","dir":"ltr"},{"lang":"sg","autonym":"Sängö","dir":"ltr"},{"lang":"sgs","autonym":"žemaitėška","dir":"ltr"},{"lang":"shi","autonym":"Taclḥit","dir":"ltr"},{"lang":"shn","autonym":"ၽႃႇသႃႇတႆး ","dir":"ltr"},{"lang":"si","autonym":"සිංහල","dir":"ltr"},{"lang":"skr","autonym":"سرائیکی","dir":"rtl"},{"lang":"sm","autonym":"Gagana Samoa","dir":"ltr"},{"lang":"smn","autonym":"anarâškielâ","dir":"ltr"},{"lang":"sn","autonym":"chiShona","dir":"ltr"},{"lang":"so","autonym":"Soomaaliga","dir":"ltr"},{"lang":"sq","autonym":"shqip","dir":"ltr"},{"lang":"srn","autonym":"Sranantongo","dir":"ltr"},{"lang":"ss","autonym":"SiSwati","dir":"ltr"}, {"lang":"st","autonym":"Sesotho","dir":"ltr"},{"lang":"stq","autonym":"Seeltersk","dir":"ltr"},{"lang":"sw","autonym":"Kiswahili","dir":"ltr"},{"lang":"szl","autonym":"ślůnski","dir":"ltr"},{"lang":"tay","autonym":"Tayal","dir":"ltr"},{"lang":"tcy","autonym":"ತುಳು","dir":"ltr"},{"lang":"tdd","autonym":"ᥖᥭᥰ ᥖᥬᥲ ᥑᥨᥒᥰ","dir":"ltr"},{"lang":"tet","autonym":"tetun","dir":"ltr"},{"lang":"ti","autonym":"ትግርኛ","dir":"ltr"},{"lang":"tk","autonym":"Türkmençe","dir":"ltr"},{"lang":"tl","autonym":"Tagalog","dir":"ltr"},{"lang":"tly","autonym":"tolışi","dir":"ltr"},{"lang":"tn","autonym":"Setswana","dir":"ltr"},{"lang":"to","autonym":"lea faka-Tonga","dir":"ltr"},{"lang":"tpi","autonym":"Tok Pisin","dir":"ltr"},{"lang":"trv","autonym":"Seediq","dir":"ltr"},{"lang":"ts","autonym":"Xitsonga","dir":"ltr"},{"lang":"tum","autonym":"chiTumbuka","dir":"ltr"},{"lang":"tw","autonym":"Twi","dir":"ltr"},{"lang":"ty","autonym":"reo tahiti","dir":"ltr"},{"lang":"tyv", "autonym":"тыва дыл","dir":"ltr"},{"lang":"udm","autonym":"удмурт","dir":"ltr"},{"lang":"ur","autonym":"اردو","dir":"rtl"},{"lang":"ve","autonym":"Tshivenda","dir":"ltr"},{"lang":"vec","autonym":"vèneto","dir":"ltr"},{"lang":"vep","autonym":"vepsän kel’","dir":"ltr"},{"lang":"vls","autonym":"West-Vlams","dir":"ltr"},{"lang":"vo","autonym":"Volapük","dir":"ltr"},{"lang":"vro","autonym":"võro","dir":"ltr"},{"lang":"wa","autonym":"walon","dir":"ltr"},{"lang":"wo","autonym":"Wolof","dir":"ltr"},{"lang":"xal","autonym":"хальмг","dir":"ltr"},{"lang":"xh","autonym":"isiXhosa","dir":"ltr"},{"lang":"xmf","autonym":"მარგალური","dir":"ltr"},{"lang":"yi","autonym":"ייִדיש","dir":"rtl"},{"lang":"yo","autonym":"Yorùbá","dir":"ltr"},{"lang":"yue","autonym":"粵語","dir":"ltr"},{"lang":"za","autonym":"Vahcuengh","dir":"ltr"},{"lang":"zgh","autonym":"ⵜⴰⵎⴰⵣⵉⵖⵜ ⵜⴰⵏⴰⵡⴰⵢⵜ","dir":"ltr"},{"lang":"zu","autonym":"isiZulu", "dir":"ltr"}],"wgSectionTranslationTargetLanguages":["ace","ady","alt","am","ami","an","ang","ann","anp","ar","ary","arz","as","ast","av","avk","awa","ay","az","azb","ba","ban","bar","bbc","bcl","bdr","be","bew","bg","bho","bi","bjn","blk","bm","bn","bo","bpy","br","bs","btm","bug","ca","cdo","ce","ceb","ch","chr","ckb","co","cr","crh","cs","cu","cy","da","dag","de","dga","din","diq","dsb","dtp","dv","dz","ee","el","eml","eo","es","et","eu","fa","fat","ff","fi","fj","fo","fon","fr","frp","frr","fur","fy","gag","gan","gcr","gl","glk","gn","gom","gor","gpe","gu","guc","gur","guw","gv","ha","hak","haw","he","hi","hif","hr","hsb","ht","hu","hy","hyw","ia","iba","ie","ig","igl","ilo","io","is","it","iu","ja","jam","jv","ka","kaa","kab","kbd","kbp","kcg","kg","kge","ki","kk","kl","km","kn","ko","koi","krc","ks","ku","kus","kv","kw","ky","lad","lb","lez","lg","li","lij","lld","lmo","ln","lo","lt","ltg","lv","mad","mai","map-bms","mdf","mg","mhr","mi","min","mk","ml","mn","mni","mnw","mos", "mr","mrj","ms","mt","mwl","my","myv","mzn","nah","nan","nap","nb","nds","nds-nl","ne","new","nia","nl","nn","nqo","nr","nso","ny","oc","om","or","os","pa","pag","pam","pap","pcd","pcm","pdc","pl","pms","pnb","ps","pt","pwn","qu","rm","rn","ro","rsk","rue","rup","rw","sa","sah","sat","sc","scn","sco","sd","se","sg","sgs","sh","shi","shn","si","sk","skr","sl","sm","smn","sn","so","sq","sr","srn","ss","st","stq","su","sv","sw","szl","ta","tay","tcy","tdd","te","tet","tg","th","ti","tk","tl","tly","tn","to","tpi","tr","trv","ts","tt","tum","tw","ty","tyv","udm","ur","uz","ve","vec","vep","vi","vls","vo","vro","wa","war","wo","wuu","xal","xh","xmf","yi","yo","yue","za","zgh","zh","zu"],"isLanguageSearcherCXEntrypointEnabled":true,"mintEntrypointLanguages":["ace","ast","azb","bcl","bjn","bh","crh","ff","fon","ig","is","ki","ks","lmo","min","sat","ss","tn","vec"],"wgWikibaseItemId":"Q101497","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile", "model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false,"wgMinervaPermissions":{"watchable":true,"watch":false},"wgMinervaFeatures":{"beta":false,"donate":true,"mobileOptionsLink":true,"categories":false,"pageIssues":true,"talkAtTop":true,"historyInPageActions":false,"overflowSubmenu":false,"tabsOnSpecials":true,"personalMenu":false,"mainMenuExpanded":false,"echo":true,"nightMode":true},"wgMinervaDownloadNamespaces":[0]};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.minerva.styles":"ready","skins.minerva.content.styles.images":"ready","mediawiki.hlist":"ready","skins.minerva.codex.styles":"ready","skins.minerva.icons":"ready","jquery.tablesorter.styles":"ready", "skins.minerva.amc.styles":"ready","ext.wikimediamessages.styles":"ready","mobile.init.styles":"ready","ext.relatedArticles.styles":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.tablesorter","skins.minerva.scripts","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","ext.popups","mobile.init","ext.echo.centralauth","ext.relatedArticles.readMore.bootstrap","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.cx.eventlogging.campaigns","ext.cx.entrypoints.mffrequentlanguages","ext.cx.entrypoints.languagesearcher.init","mw.externalguidance.init","ext.checkUser.clientHints","ext.quicksurveys.init","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.relatedArticles.styles%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.tablesorter.styles%7Cmediawiki.hlist%7Cmobile.init.styles%7Cskins.minerva.amc.styles%7Cskins.minerva.codex.styles%7Cskins.minerva.content.styles.images%7Cskins.minerva.icons%2Cstyles%7Cwikibase.client.init&only=styles&skin=minerva"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=minerva"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=minerva"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta name="theme-color" content="#eaecf0"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/1200px-Aldehyde_general_structure.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="1096"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/800px-Aldehyde_general_structure.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="730"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Aldehyde_general_structure.svg/640px-Aldehyde_general_structure.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="584"> <meta name="viewport" content="width=device-width, initial-scale=1.0, user-scalable=yes, minimum-scale=0.25, maximum-scale=5.0"> <meta property="og:title" content="Aldehyde - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="manifest" href="/w/api.php?action=webapp-manifest"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Aldehyde&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Aldehyde"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Aldehyde rootpage-Aldehyde stable issues-group-B skin-minerva action-view skin--responsive mw-mf-amc-disabled mw-mf"><div id="mw-mf-viewport"> <div id="mw-mf-page-center"> <a class="mw-mf-page-center__mask" href="#"></a> <header class="header-container header-chrome"> <div class="minerva-header"> <nav class="navigation-drawer toggle-list view-border-box"> <input type="checkbox" id="main-menu-input" class="toggle-list__checkbox" role="button" aria-haspopup="true" aria-expanded="false" aria-labelledby="mw-mf-main-menu-button"> <label role="button" for="main-menu-input" id="mw-mf-main-menu-button" aria-hidden="true" data-event-name="ui.mainmenu" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet toggle-list__toggle"> <span class="minerva-icon minerva-icon--menu"></span> <span></span> </label> <div id="mw-mf-page-left" class="menu view-border-box"> <ul id="p-navigation" class="toggle-list__list"> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--home" href="/wiki/Main_Page" data-mw="interface"> <span class="minerva-icon minerva-icon--home"></span> <span class="toggle-list-item__label">Home</span> </a> </li> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--random" href="/wiki/Special:Random" data-mw="interface"> <span class="minerva-icon minerva-icon--die"></span> <span class="toggle-list-item__label">Random</span> </a> </li> <li class="toggle-list-item skin-minerva-list-item-jsonly"> <a class="toggle-list-item__anchor menu__item--nearby" href="/wiki/Special:Nearby" data-event-name="menu.nearby" data-mw="interface"> <span class="minerva-icon minerva-icon--mapPin"></span> <span class="toggle-list-item__label">Nearby</span> </a> </li> </ul> <ul id="p-personal" class="toggle-list__list"> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--login" href="/w/index.php?title=Special:UserLogin&returnto=Aldehyde" data-event-name="menu.login" data-mw="interface"> <span class="minerva-icon minerva-icon--logIn"></span> <span class="toggle-list-item__label">Log in</span> </a> </li> </ul> <ul id="pt-preferences" class="toggle-list__list"> <li class="toggle-list-item skin-minerva-list-item-jsonly"> <a class="toggle-list-item__anchor menu__item--settings" href="/w/index.php?title=Special:MobileOptions&returnto=Aldehyde" data-event-name="menu.settings" data-mw="interface"> <span class="minerva-icon minerva-icon--settings"></span> <span class="toggle-list-item__label">Settings</span> </a> </li> </ul> <ul id="p-donation" class="toggle-list__list"> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--donate" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en&utm_key=minerva" data-event-name="menu.donate" data-mw="interface"> <span class="minerva-icon minerva-icon--heart"></span> <span class="toggle-list-item__label">Donate</span> </a> </li> </ul> <ul class="hlist"> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--about" href="/wiki/Wikipedia:About" data-mw="interface"> <span class="toggle-list-item__label">About Wikipedia</span> </a> </li> <li class="toggle-list-item "> <a class="toggle-list-item__anchor menu__item--disclaimers" href="/wiki/Wikipedia:General_disclaimer" data-mw="interface"> <span class="toggle-list-item__label">Disclaimers</span> </a> </li> </ul> </div> <label class="main-menu-mask" for="main-menu-input"></label> </nav> <div class="branding-box"> <a href="/wiki/Main_Page"> <span><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </span> </a> </div> <form action="/w/index.php" method="get" class="minerva-search-form"> <div class="search-box"> <input type="hidden" name="title" value="Special:Search"/> <input class="search skin-minerva-search-trigger" id="searchInput" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f"> <span class="search-box-icon-overlay"><span class="minerva-icon minerva-icon--search"></span> </span> </div> <button id="searchIcon" class="cdx-button cdx-button--size-large cdx-button--icon-only cdx-button--weight-quiet skin-minerva-search-trigger"> <span class="minerva-icon minerva-icon--search"></span> <span>Search</span> </button> </form> <nav class="minerva-user-navigation" aria-label="User navigation"> </nav> </div> </header> <main id="content" class="mw-body"> <div class="banner-container"> <div id="siteNotice"></div> </div> <div class="pre-content heading-holder"> <div class="page-heading"> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Aldehyde</span></h1> <div class="tagline"></div> </div> <ul id="p-associated-pages" class="minerva__tab-container"> <li class="minerva__tab selected"> <a class="minerva__tab-text" href="/wiki/Aldehyde" rel="" data-event-name="tabs.subject">Article</a> </li> <li class="minerva__tab "> <a class="minerva__tab-text" href="/wiki/Talk:Aldehyde" rel="discussion" data-event-name="tabs.talk">Talk</a> </li> </ul> <nav class="page-actions-menu"> <ul id="p-views" class="page-actions-menu__list"> <li id="language-selector" class="page-actions-menu__list-item"> <a role="button" href="#p-lang" data-mw="interface" data-event-name="menu.languages" title="Language" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet language-selector"> <span class="minerva-icon minerva-icon--language"></span> <span>Language</span> </a> </li> <li id="page-actions-watch" class="page-actions-menu__list-item"> <a role="button" id="ca-watch" href="/w/index.php?title=Special:UserLogin&returnto=Aldehyde" data-event-name="menu.watch" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet menu__item--page-actions-watch"> <span class="minerva-icon minerva-icon--star"></span> <span>Watch</span> </a> </li> <li id="page-actions-edit" class="page-actions-menu__list-item"> <a role="button" id="ca-edit" href="/w/index.php?title=Aldehyde&action=edit" data-event-name="menu.edit" data-mw="interface" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet edit-page menu__item--page-actions-edit"> <span class="minerva-icon minerva-icon--edit"></span> <span>Edit</span> </a> </li> </ul> </nav>  <div id="mw-content-subtitle"></div> </div> <div id="bodyContent" class="content"> <div id="mw-content-text" class="mw-body-content"><script>function mfTempOpenSection(id){var block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"> <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><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> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Structure_and_bonding"><span class="tocnumber">1</span> <span class="toctext">Structure and bonding</span></a></li> <li class="toclevel-1 tocsection-2"><a href="#Physical_properties_and_characterization"><span class="tocnumber">2</span> <span class="toctext">Physical properties and characterization</span></a></li> <li class="toclevel-1 tocsection-3"><a href="#Applications_and_occurrence"><span class="tocnumber">3</span> <span class="toctext">Applications and occurrence</span></a> <ul> <li class="toclevel-2 tocsection-4"><a href="#Naturally_occurring_aldehydes"><span class="tocnumber">3.1</span> <span class="toctext">Naturally occurring aldehydes</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-5"><a href="#Synthesis"><span class="tocnumber">4</span> <span class="toctext">Synthesis</span></a> <ul> <li class="toclevel-2 tocsection-6"><a href="#Hydroformylation"><span class="tocnumber">4.1</span> <span class="toctext">Hydroformylation</span></a></li> <li class="toclevel-2 tocsection-7"><a href="#Oxidative_routes"><span class="tocnumber">4.2</span> <span class="toctext">Oxidative routes</span></a></li> <li class="toclevel-2 tocsection-8"><a href="#Specialty_methods"><span class="tocnumber">4.3</span> <span class="toctext">Specialty methods</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-9"><a href="#Common_reactions"><span class="tocnumber">5</span> <span class="toctext">Common reactions</span></a> <ul> <li class="toclevel-2 tocsection-10"><a href="#Acid-base_reactions"><span class="tocnumber">5.1</span> <span class="toctext">Acid-base reactions</span></a></li> <li class="toclevel-2 tocsection-11"><a href="#Enolization"><span class="tocnumber">5.2</span> <span class="toctext">Enolization</span></a></li> <li class="toclevel-2 tocsection-12"><a href="#Reduction"><span class="tocnumber">5.3</span> <span class="toctext">Reduction</span></a></li> <li class="toclevel-2 tocsection-13"><a href="#Oxidation"><span class="tocnumber">5.4</span> <span class="toctext">Oxidation</span></a></li> <li class="toclevel-2 tocsection-14"><a href="#Nucleophilic_addition_reactions"><span class="tocnumber">5.5</span> <span class="toctext">Nucleophilic addition reactions</span></a> <ul> <li class="toclevel-3 tocsection-15"><a href="#Oxygen_nucleophiles"><span class="tocnumber">5.5.1</span> <span class="toctext">Oxygen nucleophiles</span></a></li> <li class="toclevel-3 tocsection-16"><a href="#Nitrogen_nucleophiles"><span class="tocnumber">5.5.2</span> <span class="toctext">Nitrogen nucleophiles</span></a></li> <li class="toclevel-3 tocsection-17"><a href="#Carbon_nucleophiles"><span class="tocnumber">5.5.3</span> <span class="toctext">Carbon nucleophiles</span></a></li> <li class="toclevel-3 tocsection-18"><a href="#Bisulfite_reaction"><span class="tocnumber">5.5.4</span> <span class="toctext">Bisulfite reaction</span></a></li> </ul> </li> <li class="toclevel-2 tocsection-19"><a href="#More_complex_reactions"><span class="tocnumber">5.6</span> <span class="toctext">More complex reactions</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-20"><a href="#Dialdehydes"><span class="tocnumber">6</span> <span class="toctext">Dialdehydes</span></a></li> <li class="toclevel-1 tocsection-21"><a href="#Biochemistry"><span class="tocnumber">7</span> <span class="toctext">Biochemistry</span></a></li> <li class="toclevel-1 tocsection-22"><a href="#Examples_of_aldehydes"><span class="tocnumber">8</span> <span class="toctext">Examples of aldehydes</span></a></li> <li class="toclevel-1 tocsection-23"><a href="#Examples_of_dialdehydes"><span class="tocnumber">9</span> <span class="toctext">Examples of dialdehydes</span></a></li> <li class="toclevel-1 tocsection-24"><a href="#Uses"><span class="tocnumber">10</span> <span class="toctext">Uses</span></a></li> <li class="toclevel-1 tocsection-25"><a href="#Nomenclature"><span class="tocnumber">11</span> <span class="toctext">Nomenclature</span></a> <ul> <li class="toclevel-2 tocsection-26"><a href="#IUPAC_names_for_aldehydes"><span class="tocnumber">11.1</span> <span class="toctext">IUPAC names for aldehydes</span></a></li> <li class="toclevel-2 tocsection-27"><a href="#Etymology"><span class="tocnumber">11.2</span> <span class="toctext">Etymology</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-28"><a href="#See_also"><span class="tocnumber">12</span> <span class="toctext">See also</span></a></li> <li class="toclevel-1 tocsection-29"><a href="#References"><span class="tocnumber">13</span> <span class="toctext">References</span></a></li> <li class="toclevel-1 tocsection-30"><a href="#External_links"><span class="tocnumber">14</span> <span class="toctext">External links</span></a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=1" title="Edit section: Structure and bonding" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Physical_properties_and_characterization">Physical properties and characterization</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=2" title="Edit section: Physical properties and characterization" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Applications_and_occurrence">Applications and occurrence</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=3" title="Edit section: Applications and occurrence" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Important_Aldehyde_Structures.svg" class="mw-file-description"><noscript><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" data-file-width="1718" data-file-height="292"></noscript><span class="lazy-image-placeholder" style="width: 830px;height: 141px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Important_Aldehyde_Structures.svg/830px-Important_Aldehyde_Structures.svg.png" data-width="830" data-height="141" data-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-class="mw-file-element"> </span></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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=4" title="Edit section: Naturally occurring aldehydes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=5" title="Edit section: Synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> <div class="mw-heading mw-heading3"><h3 id="Hydroformylation">Hydroformylation</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=6" title="Edit section: Hydroformylation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=7" title="Edit section: Oxidative routes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=8" title="Edit section: Specialty methods" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Common_reactions">Common reactions</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=9" title="Edit section: Common reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> <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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=10" title="Edit section: Acid-base reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=11" title="Edit section: Enolization" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=12" title="Edit section: Reduction" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=13" title="Edit section: Oxidation" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=14" title="Edit section: Nucleophilic addition reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=15" title="Edit section: Oxygen nucleophiles" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=16" title="Edit section: Nitrogen nucleophiles" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=17" title="Edit section: Carbon nucleophiles" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=18" title="Edit section: Bisulfite reaction" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=19" title="Edit section: More complex reactions" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Dialdehydes">Dialdehydes</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=20" title="Edit section: Dialdehydes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-6 collapsible-block" id="mf-section-6"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(7)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=21" title="Edit section: Biochemistry" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-7 collapsible-block" id="mf-section-7"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(8)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Examples_of_aldehydes">Examples of aldehydes</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=22" title="Edit section: Examples of aldehydes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-8 collapsible-block" id="mf-section-8"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(9)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Examples_of_dialdehydes">Examples of dialdehydes</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=23" title="Edit section: Examples of dialdehydes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-9 collapsible-block" id="mf-section-9"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(10)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Uses">Uses</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=24" title="Edit section: Uses" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-10 collapsible-block" id="mf-section-10"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(11)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=25" title="Edit section: Nomenclature" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-11 collapsible-block" id="mf-section-11"> <div class="mw-heading mw-heading3"><h3 id="IUPAC_names_for_aldehydes">IUPAC names for aldehydes</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=26" title="Edit section: IUPAC names for aldehydes" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=27" title="Edit section: Etymology" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(12)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="See_also">See also</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=28" title="Edit section: See also" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-12 collapsible-block" id="mf-section-12"> <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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(13)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="References">References</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=29" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-13 collapsible-block" id="mf-section-13"> <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). "Oxidation". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. pp. 1–103. <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.a18_261.pub2">10.1002/14356007.a18_261.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30385-4" title="Special:BookSources/978-3-527-30385-4"><bdi>978-3-527-30385-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Oxidation&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=1-103&rft.date=2015&rft_id=info%3Adoi%2F10.1002%2F14356007.a18_261.pub2&rft.isbn=978-3-527-30385-4&rft.aulast=Teles&rft.aufirst=J.+Henrique&rft.au=Hermans%2C+Ive&rft.au=Franz%2C+Gerhard&rft.au=Sheldon%2C+Roger+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-CH2O-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-CH2O_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CH2O_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Reuss, G.; Disteldorf, W.; Gamer, A. O. and Hilt, A. (2005) "Formaldehyde" 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.a11_619">10.1002/14356007.a11_619</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 id="CITEREFRatcliffe,_R._W.1988" class="citation journal cs1">Ratcliffe, R. W. (1988). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv6p0373">"Oxidation with the Chromium Trioxide-Pyridine Complex Prepared in situ: 1-Decanal"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Oxidation+with+the+Chromium+Trioxide-Pyridine+Complex+Prepared+in+situ%3A+1-Decanal&rft.date=1988&rft.au=Ratcliffe%2C+R.+W.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv6p0373&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 6, p. 373</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=373&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></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 id="CITEREFŌeda1934" class="citation journal cs1">Ōeda, Haruomi (1934). <a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.9.8">"Oxidation of some α-hydroxy-acids with lead tetraacetate"</a>. <i>Bulletin of the Chemical Society of Japan</i>. <b>9</b> (1): 8–14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.9.8">10.1246/bcsj.9.8</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+of+the+Chemical+Society+of+Japan&rft.atitle=Oxidation+of+some+%CE%B1-hydroxy-acids+with+lead+tetraacetate&rft.volume=9&rft.issue=1&rft.pages=8-14&rft.date=1934&rft_id=info%3Adoi%2F10.1246%2Fbcsj.9.8&rft.aulast=%C5%8Ceda&rft.aufirst=Haruomi&rft_id=https%3A%2F%2Fdoi.org%2F10.1246%252Fbcsj.9.8&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNwaukwaKeehn1982" class="citation journal cs1">Nwaukwa, Stephen; Keehn, Philip (1982). "Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite [Ca(OCl)2]". <i>Tetrahedron Letters</i>. <b>23</b> (31): 3135–3138. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2800%2988578-0">10.1016/S0040-4039(00)88578-0</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Oxidative+cleavage+of+%CE%B1-diols%2C+%CE%B1-diones%2C+%CE%B1-hydroxy-ketones+and+%CE%B1-hydroxy-+and+%CE%B1-keto+acids+with+calcium+hypochlorite+%5BCa%28OCl%292%5D&rft.volume=23&rft.issue=31&rft.pages=3135-3138&rft.date=1982&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2988578-0&rft.aulast=Nwaukwa&rft.aufirst=Stephen&rft.au=Keehn%2C+Philip&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeerman1913" class="citation journal cs1">Weerman, R.A. (1913). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1427615">"Einwirkung von Natriumhypochlorit auf Amide ungesättigter Säuren"</a>. <i>Justus Liebigs Annalen der Chemie</i>. <b>401</b> (1): 1–20. <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%2Fjlac.19134010102">10.1002/jlac.19134010102</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Justus+Liebigs+Annalen+der+Chemie&rft.atitle=Einwirkung+von+Natriumhypochlorit+auf+Amide+unges%C3%A4ttigter+S%C3%A4uren&rft.volume=401&rft.issue=1&rft.pages=1-20&rft.date=1913&rft_id=info%3Adoi%2F10.1002%2Fjlac.19134010102&rft.aulast=Weerman&rft.aufirst=R.A.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1427615&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEverettLane1946" class="citation book cs1">Everett, Wallis; Lane, John (1946). <i>The Hofmann Reaction</i>. Organic Reactions. Vol. 3. pp. 267–306. <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%2F0471264180.or003.07">10.1002/0471264180.or003.07</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471005285" title="Special:BookSources/9780471005285"><bdi>9780471005285</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+Hofmann+Reaction&rft.series=Organic+Reactions&rft.pages=267-306&rft.date=1946&rft_id=info%3Adoi%2F10.1002%2F0471264180.or003.07&rft.isbn=9780471005285&rft.aulast=Everett&rft.aufirst=Wallis&rft.au=Lane%2C+John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSutton,_PeterWhittall,_John2012" class="citation book cs1">Sutton, Peter; Whittall, John (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WlODZ-WX8vIC&q=9781119991397"><i>Practical Methods for Biocatalysis and Biotransformations 2</i></a>. Chichester, West Sussex: John Wiley & Sons, Ltd. pp. 199–202. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781119991397" title="Special:BookSources/9781119991397"><bdi>9781119991397</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Practical+Methods+for+Biocatalysis+and+Biotransformations+2&rft.place=Chichester%2C+West+Sussex&rft.pages=199-202&rft.pub=John+Wiley+%26+Sons%2C+Ltd.&rft.date=2012&rft.isbn=9781119991397&rft.au=Sutton%2C+Peter&rft.au=Whittall%2C+John&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWlODZ-WX8vIC%26q%3D9781119991397&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</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://www.iswori.com.np/2023/07/aldehyde-and-ketone-class-12-chemistry.html">"Aldehyde and Ketone - NEB Class 12 Chemistry 2080"</a>. <i>Iswori Education</i>. 2023-07-29<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-07-29</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Iswori+Education&rft.atitle=Aldehyde+and+Ketone+-+NEB+Class+12+Chemistry+2080&rft.date=2023-07-29&rft_id=https%3A%2F%2Fwww.iswori.com.np%2F2023%2F07%2Faldehyde-and-ketone-class-12-chemistry.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1">"Aldehyde Tautomerism". <a rel="nofollow" class="external text" href="https://www.britannica.com/science/aldehyde/Tautomerism"><i>Encyclopedia Britannica</i></a>. 4 June 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Aldehyde+Tautomerism&rft.btitle=Encyclopedia+Britannica&rft.date=2024-06-04&rft_id=https%3A%2F%2Fwww.britannica.com%2Fscience%2Faldehyde%2FTautomerism&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWarrenWyatt2008" class="citation book cs1">Warren, Stuart; Wyatt, Paul (2008). <i>Organic synthesis: the disconnection approach</i> (2nd ed.). Wiley. pp. 129–133. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-71236-8" title="Special:BookSources/978-0-470-71236-8"><bdi>978-0-470-71236-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+synthesis%3A+the+disconnection+approach&rft.pages=129-133&rft.edition=2nd&rft.pub=Wiley&rft.date=2008&rft.isbn=978-0-470-71236-8&rft.aulast=Warren&rft.aufirst=Stuart&rft.au=Wyatt%2C+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCareySundberg2007" class="citation book cs1 cs1-prop-long-vol">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry</i>. Vol. A: Structure and Mechanisms (5th ed.). Springer. pp. 601–608. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-44899-2" title="Special:BookSources/978-0-387-44899-2"><bdi>978-0-387-44899-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry&rft.pages=601-608&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft.isbn=978-0-387-44899-2&rft.aulast=Carey&rft.aufirst=Francis+A.&rft.au=Sundberg%2C+Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-Fuson-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fuson_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Fuson_18-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShrinerHermannMorrillCurtin1997" class="citation book cs1">Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C. (1997). <i>The Systematic Identification of Organic Compounds</i>. John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-59748-3" title="Special:BookSources/978-0-471-59748-3"><bdi>978-0-471-59748-3</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+Systematic+Identification+of+Organic+Compounds&rft.pub=John+Wiley+%26+Sons&rft.date=1997&rft.isbn=978-0-471-59748-3&rft.aulast=Shriner&rft.aufirst=R.+L.&rft.au=Hermann%2C+C.+K.+F.&rft.au=Morrill%2C+T.+C.&rft.au=Curtin%2C+D.+Y.&rft.au=Fuson%2C+R.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFurigayBoucherMizgierBrindle2018" class="citation journal cs1">Furigay, Maxwell H.; Boucher, Maria M.; Mizgier, Nikola A.; Brindle, Cheyenne S. (2018-04-02). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933314">"Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol"</a>. <i>Journal of Visualized Experiments</i> (134): 57639. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3791%2F57639">10.3791/57639</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/1940-087X">1940-087X</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933314">5933314</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29658940">29658940</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+Visualized+Experiments&rft.atitle=Separation+of+Aldehydes+and+Reactive+Ketones+from+Mixtures+Using+a+Bisulfite+Extraction+Protocol&rft.issue=134&rft.pages=57639&rft.date=2018-04-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5933314%23id-name%3DPMC&rft.issn=1940-087X&rft_id=info%3Apmid%2F29658940&rft_id=info%3Adoi%2F10.3791%2F57639&rft.aulast=Furigay&rft.aufirst=Maxwell+H.&rft.au=Boucher%2C+Maria+M.&rft.au=Mizgier%2C+Nikola+A.&rft.au=Brindle%2C+Cheyenne+S.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5933314&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChenFerreiraGrossRosen2014" class="citation journal cs1">Chen, Che-Hong; Ferreira, Julio Cesar Batista; Gross, Eric R.; Rosen, Daria Mochly (1 January 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929114">"Targeting Aldehyde Dehydrogenase 2: New Therapeutic Opportunities"</a>. <i>Physiological Reviews</i>. <b>94</b> (1): 1–34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fphysrev.00017.2013">10.1152/physrev.00017.2013</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929114">3929114</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24382882">24382882</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physiological+Reviews&rft.atitle=Targeting+Aldehyde+Dehydrogenase+2%3A+New+Therapeutic+Opportunities&rft.volume=94&rft.issue=1&rft.pages=1-34&rft.date=2014-01-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3929114%23id-name%3DPMC&rft_id=info%3Apmid%2F24382882&rft_id=info%3Adoi%2F10.1152%2Fphysrev.00017.2013&rft.aulast=Chen&rft.aufirst=Che-Hong&rft.au=Ferreira%2C+Julio+Cesar+Batista&rft.au=Gross%2C+Eric+R.&rft.au=Rosen%2C+Daria+Mochly&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3929114&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAldehyde" class="Z3988"></span></span> </li> <li id="cite_note-aliphald-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-aliphald_21-0">^</a></b></span> <span class="reference-text">Kohlpaintner, C.; Schulte, M.; Falbe, J.; Lappe, P. and Weber, J. (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> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(14)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="External_links">External links</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Aldehyde&action=edit&section=30" title="Edit section: External links" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-14 collapsible-block" id="mf-section-14"> <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><noscript><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" data-file-width="512" data-file-height="512"></noscript><span class="lazy-image-placeholder" style="width: 40px;height: 40px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" data-alt="" data-width="40" data-height="40" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-class="mw-file-element"> </span></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/aldehyde" class="extiw" title="wiktionary:Special:Search/aldehyde">aldehyde</a></b></i> in Wiktionary, the free dictionary.</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><noscript><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" data-file-width="300" data-file-height="355"></noscript><span class="lazy-image-placeholder" style="width: 34px;height: 40px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" data-alt="" data-width="34" data-height="40" data-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-class="mw-file-element"> </span></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/Aldehyde" class="extiw" title="q:Special:Search/Aldehyde">Aldehyde</a></b></i>.</div></div> </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 .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></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" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div>    </section></div> <noscript><img src="https://login.m.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&mobile=1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Aldehyde&oldid=1256928529">https://en.wikipedia.org/w/index.php?title=Aldehyde&oldid=1256928529</a>"</div></div> </div> <div class="post-content" id="page-secondary-actions"> </div> </main> <footer class="mw-footer minerva-footer" role="contentinfo"> <a class="last-modified-bar" href="/w/index.php?title=Aldehyde&action=history"> <div class="post-content last-modified-bar__content"> <span class="minerva-icon minerva-icon-size-medium minerva-icon--modified-history"></span> <span class="last-modified-bar__text modified-enhancement" data-user-name="Benbest" data-user-gender="male" data-timestamp="1731397469"> <span>Last edited on 12 November 2024, at 07:44</span> </span> <span class="minerva-icon minerva-icon-size-small minerva-icon--expand"></span> </div> </a> <div class="post-content footer-content"> <div id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><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" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%86%9B" title="醛 – Cantonese" lang="yue" hreflang="yue" data-title="醛" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%86%9B" title="醛 – Chinese" lang="zh" hreflang="zh" data-title="醛" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 12 November 2024, at 07:44<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-terms-use"><a href="https://foundation.m.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use">Terms of Use</a></li> <li id="footer-places-desktop-toggle"><a id="mw-mf-display-toggle" href="//en.wikipedia.org/w/index.php?title=Aldehyde&mobileaction=toggle_view_desktop" data-event-name="switch_to_desktop">Desktop</a></li> </ul> </div> </footer> </div> </div> <div class="mw-notification-area" data-mw="interface"></div>  <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.canary-846d5d75fc-ltnck","wgBackendResponseTime":168,"wgPageParseReport":{"limitreport":{"cputime":"0.978","walltime":"1.176","ppvisitednodes":{"value":4784,"limit":1000000},"postexpandincludesize":{"value":100331,"limit":2097152},"templateargumentsize":{"value":4489,"limit":2097152},"expansiondepth":{"value":12,"limit":100},"expensivefunctioncount":{"value":4,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":114568,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1012.657 1 -total"," 32.42% 328.317 1 Template:Reflist"," 12.76% 129.201 3 Template:Lang"," 11.59% 117.324 1 Template:Functional_Groups"," 11.55% 116.993 3 Template:Navbox"," 11.47% 116.156 1 Template:March6th"," 9.13% 92.433 28 Template:Chem2"," 7.83% 79.321 1 Template:Short_description"," 6.46% 65.375 9 Template:Cite_book"," 5.76% 58.300 1 Template:Authority_control"]},"scribunto":{"limitreport-timeusage":{"value":"0.643","limit":"10.000"},"limitreport-memusage":{"value":16793603,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-6b7f745dd4-r6k9d","timestamp":"20241125144302","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Aldehyde","url":"https:\/\/en.wikipedia.org\/wiki\/Aldehyde","sameAs":"http:\/\/www.wikidata.org\/entity\/Q101497","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q101497","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2002-02-02T06:00:22Z","dateModified":"2024-11-12T07:44:29Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/e\/ed\/Aldehyde_general_structure.svg","headline":"organic compounds containing a functional group with the structure \u2212CHO, consisting of a carbonyl center (a carbon double-bonded to oxygen) with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain"}</script><script>(window.NORLQ=window.NORLQ||[]).push(function(){var ns,i,p,img;ns=document.getElementsByTagName('noscript');for(i=0;i<ns.length;i++){p=ns[i].nextSibling;if(p&&p.className&&p.className.indexOf('lazy-image-placeholder')>-1){img=document.createElement('img');img.setAttribute('src',p.getAttribute('data-src'));img.setAttribute('width',p.getAttribute('data-width'));img.setAttribute('height',p.getAttribute('data-height'));img.setAttribute('alt',p.getAttribute('data-alt'));p.parentNode.replaceChild(img,p);}}});</script> </body> </html>