Ketones: kiimikaad iyo go'aanka

chemistry Organic - sayniska uu yahay mid aad u adag, laakiin xiiso leh. Sababtoo ah xeryahooda oo ka mid ah xubno ka mid ah tiro ka mid ah isku xigxiga oo kala duwan iyo kor u formation of kala duwan guryaha walxaha. Ha ka fikiro si aynu xarunta koox carbonyl loo yaqaan "ketones" (kiimikaad, astaamaha jirka, hababka ay Avv). Iyo in la isbarbardhigo la waxyaabaha kale ee ah nooc ka mid ah - aldehydes.

ketones

Hadalkaasu waa magaca guud ee fasal ka mid ah dabeecadda organic walxaha, taagoo of taas oo kooxda carbonyl (C = O) ee ku xidhan yahay laba xag carbon.

Sida laga soo xigtay in ay qaab-dhismeedka la mid ah aldehydes ketones iyo acids carboxylic. Si kastaba ha ahaatee, ay Joogaan mar laba atamka C (carbon ama carbon) xiran C = O.

formula

formula guud ee fasalka this xeryahooda waa sida soo socota: R ₁ -CO-R _2.

Si aad uga dhigto mid la fahmi karo, sida caadiga ah, waxaa sidaas ku qoran.

Waxaa C = O - waa koox carbonyl ah. A _{1 iyo} R R ₂ - a xag carbon. In ay meel laga yaabaa in xeryahooda kala duwan, laakiin ay ka kooban waa in ay ahaadaan carbon.

Aldehydes iyo ketones

guryaha jirka iyo kiimikada oo ka mid ah kooxaha ka mid ah walxaha arrin la mid ah midba midka kale waa. Sababtan awgeed, waxay inta badan la isku tixgeliyo.

Xaqiiqada ah in aldehydes ayaa sidoo kale ku jira group carbonyl ee u taagoo ay a. Waxay xitaa la ketones of formula aad u la mid ah. Si kastaba ha ahaatee, haddii walxaha C = O lifaaqan laba xag markaas aldehyde waa mid keliya, halkii labaad - eb hydrogen: R-CO-H.

Tusaale ahaan, caanaha ee fasalka ka mid ah walxaha - formaldehyde, oo dhan more cajiib ah sida formalin.

Iyada oo ku saleysan formula ee CH ₂ O, waxaa la arkay in koox carbonyl ay aan la xiriira mid ka mid ah laakiin la laba atamka N.

guryaha jirka

Ka hor inta aan la kiimikaad ee aldehydes iyo ketones ka qabtaan, waa in ay tixgeliyaan astaamaha jirka.

• Ketones - a cunnooyinka adkaha ah low-barafka ama cabitaanno ah la Degenaansho. Xubnaha hoose ee fasalka this si fiican u kala diri ee H ₂ O iyo sidoo kale ka jawaabay qase organic.
  wakiilada ee Shakhsiga (tus CH ₃ COCH ₃₎ la yaabka lahaa L. biyo, iyo gabi ahaanba in kasta oo Joogaba.
  Marka la barbardhigo ah alcohols iyo acids carboxylic, ketones leeyihiin Degenaansho weyn oo leh miisaan la mid ah kelli. Taasina waxay keentaa in ay awood xeryahooda, kuwaas oo ah in la abuuro xiriir la H, sida laga yaabaa H-CO-R.
• Noocyada kala duwan ee aldehydes noqon kartaa gobolada kala duwan ee xulkii. Tan iyo sare R-CO-H - waa adkaha beelaya. dareere ah, qayb ka mid ah kaas oo la qaso H ganaax ₂ O, laakiin kaliya qaar ka mid ah iyaga ka mid ah waa L. biyo, laakiin mar dambe sii jirin - Hoose.
  Ugu fudud ee noocan ah ee walxaha - aldehyde formic - gaas oo waa caraf pungent hanti. Qoraalkan waa si fiican u milma ee H ₂ O.

The ketones ugu fiican u yaqaan

Waxaa jiraa waxyaaba badan R ₁ -CO-R _2, si kastaba ha ahaatee, si fiican u yaqaan ma aha kuwo aad u badan. Tani waxay ugu horrayn waa dimethyl ketonka, kaas oo aynu wada ognahay sida acetone. Sidoo kale saaxiibkii dareeraha - butanone ama sidii ay u si fiican u yaqaan - methylethylketone.

Ka mid ah ketones kale, guryaha kiimikada kuwaas oo si ballaaran loo isticmaalo warshadaha - acetophenone (metilfenilketon). Si ka duwan acetone iyo butanone, urta waa arrin wacan, taas oo ah sababta loo isticmaalaa in perfumery.

Tusaale ahaan, cyclohexanone la xidhiidho wakiilo caadiga R ₁ -CO-R _2, oo waxaa inta badan la isticmaalo wax soo saarka ee solvents.

In aan ku xuso diketones ah. Horyaalka noocan oo kale ah waa R ₁ -CO-R _2, kuwaas oo mid ka mid ma aha, laakiin labada kooxood carbonyl ee ka kooban. Sidaas darteed, ay formula waa: R ₁ -CO-CO-R _2. Mid ka mid ah ugu sahlan, laakiin caadi ahaan loo isticmaalo warshadaha cuntada waa diketones wakiilada, diacetyl (2,3-butanedione).

Waxyaabahani - ay tahay oo kaliya liiska yar oo ah cilmibaadhe ku dhexsameeysmo ketones (guryaha kiimikada ayaa hoos looga hadlay). Dhab ahaantii, waxaa ka badan yihiin, laakiin dhammaantiin ma aha codsiyada la helay. The dheeraad ah oo ku waa mid tixgalin mudan in qaar badan oo iyaga ka mid yihiin sun ah.

The guryaha kiimikada ee ketones

Muqaadaraadka of this category ay awoodaan in ay fal la walxaha kala duwan. Tani waa waxa uu yahay guryaha ay kiimikada gaar ah.

• Ketones waa ay awoodaan in ay isu soo lifaaq si H (reaction hydrogenation). Si kastaba ha ahaatee, waayo sheyga cadaanyo waxay u baahan tahay joogitaanka Xoojiya qaab atamka bir ah nickel, cobalt, Cuprum, platina, palladium, iyo kuwa kale. Reaction R ₁ -CO-R ₂ xuubsiiban in alcohols sare.
  Sidoo kale, by ficil ay goobjoog ka ahaayeen ahaan nuguli uu a hydrogenous alkali bir ama glycols mg laga helay ketones.
• Ketones isagoo ugu yaraan hal eb Alfa-hydrogenic u muuqdaan in ay ku dhici sarkhaansan tautomerization Keto-enol. Waxaa la catalyzed ma aha oo kaliya by yahay ee acids, laakiin sidoo kale waxyaabaha aasaasiga ah. Sida caadiga ah, foomka Keto waa arrin ka badan isu deggan badan enol. hoganaya Taasi waxay suurto gal ah in synthesize ketones ah by fuuq alkynes. Foomamka xasilinta enol-Keto qaraabo ah conjugation ku keenaysaa in R ashitada halkii xoog leh ₁ -CO-R ₂ (marka la barbar dhigo alkanes).
• Waxyaabahani waxay geli kari cadaanyo la ammonia. Si kastaba ha ahaatee, waxay ku dhacaan aad si tartiib ah.
• Ketones fal la hydrocyanic acid. Tani waxa ay keentey in α-oksinitrily, saponification oo kor u dhacdo α-hydroxyacids.
• Entry in fal la halides alkylmagnesium keenaysaa in formation of alcohols sare.
• Ku biirista NaHSO ₃ kordhinayaan in gidrosulfitnyh (bisulfite) taagayo. Waxaa haboon in la xasuusnaado in falcelinta ee taxanahan dufan yihiin oo kaliya in ay galaan ketones methyl awoodaan.
  Waxa intaa dheer in ketones, sida fal la hydrosulphite sodium iyo laga yaabaa aldehydes.
  Marka kululeeyo xal of NaHCO ₃ (baking soda) ama acid macdanta ah, taagayo of NaHSO ₃ yaabaa in cawisa Ulasocto sii daayo ketonka free.
• Inta lagu guda jiro dareen, R ₁ -CO-R ₂ la NH ₂ OH (hydroxylamine) iyo ketoximes sameeyay sida byproduct a - H ₂ O.
• In dareen diidmo ku lug hydrazine sameeyay hydrazones (ratio of walax isku daro - 1: 1) ama azines (1: 2).
  Haddii la helay ay sabab u tahay wax soo saarka ee reaction (hydrazone) sarkhaansan yihiin heerkulka la hydroxide potassium fal, iyo N taagan saturates. Nidaamkan waxaa loo yaqaan reaction Kishner.
• Sida aynu hore u kor ku xusan, aldehydes iyo ketones iyo kiimikaad oo ay leeyihiin habka aqbaliddoodii la mid ah. Sayidka acetals R ₁ -CO-R ₂ foomka ka dhib badan acetals R-CO-H. Waxay u muuqan sabab u ah ketones in ay esters iyo orthoformic orthosilicic acid.
• In deegaan uruureen sare ee alkalis (tus, by kulaylinta la H₂SO₄ xoog) R ₁ -CO-R ₂ waxaa lagu sakhiray in fuuq-bax ah intermolecular si ay u sameeyaan ketones roodhida.
• Haddii cadaanyo la R ₁ -CO-R ₂ waxaa ku jira alkali, ketones mari uumiga aldol. Sidaas awgeed, ku alcohols β-Keto sameeyay in si fudud ku waayi kartaa Britain ayaa ka mid ah H ₂ O.
• Waxay jeelyihiin in guryaha kiimikada weyn isu muujin in Tusaale ketones acetone jawaabay xabagta mesityl. In kiiska noocan oo kale ah, wax cusub oo lagu magacaabo "phorone".
• Sidoo kale kiimikaad oo ah walaxda organic ka mid ah cadaanyo Leuckart-Wallach, kaas oo ku kordhinaya yareynta ketones.

Sababo la siin R1-CO-Red2

Markuu barasho leh sifooyinka walxaha ee su'aasha, waxaa lagama maarmaan ah in la ogaado hababka ugu badan ee ay Avv.

• Mid ka mid ah dareen diidmo ugu fiican u yaqaan for diyaarinta ketones waa alkylation iyo acylation xeryahooda leedahay beduliyum in joogitaanka Xoojiya acidic (AlCl _3, FeCI _3, acids macdanta, oxides, Beeyada sarrifka waxbarashada, iyo wixii la mid ah). Habkani waxaa loo yaqaanaa sida cadaanyo Friedel-farshaxan.
• Ketones waa la dhexsameeysmo by ketimines hydrolysis iyo Vic-diol. In the case of dambe waxay u baahan tahay joogitaanka acid macdanta ah sidii qaar kaaliya.
• Waxaa sidoo kale loo isticmaalaa in lagu soo saaro ketones homolog of fuuq alxamaad ama sida waxa loo yaqaan - falcelinta Kucherov.
• Xasaasiyada Guben-Gesha.
• Cyclization Ruzicka haboon tsikloketonov Avv.
• Sidoo kale, xogta walaxda ka peroksoefirov jaamacadda isticmaalaya rearrangement Kriege miino.
• Waxaa jira habab dhowr ah ereygu wuxuu ahaa ee ketones inta lagu guda jiro dareen diidmo oo lagu qayilo ee alcohols sare. Iyadoo ku xiran ee xeryahooda firfircoon yihiin 4 ficil: Swern Kornblum, Corey-Kim iyo Parikh-Doering.

baaxadda

Iyadoo la macaamilooday guryaha kiimikada iyo soo saaraan ketones waa in ay ogaadaan meesha ay walxaha kuwan waxaa sidoo kale loo isticmaalaa.

Sida kor ku xusan, wax badan oo ka mid ah waxaa loo isticmaalaa in industry kiimikada sida qase for lacquers, enamels, iyo sidoo kale wax soo saarka ee polymers.

Intaa waxaa dheer, qaar ka mid ah R ₁ -CO-R ₂ si fiican u xaqiijiyay sida wax dhadhan. Sida oo kale, ketones (benzophenone, acetophenone, iwm) waxaa loo isticmaalaa in perfumery iyo cunto karinta.

Sidoo kale acetophenone loo isticmaalaa sida qayb wax soo saarka ee kiniiniga hurdada.

Benzophenone, ay sabab u tahay kartida si uu u nuugo shucaaca waxyeelada leh - waa qayb caadi ah ee la isku qurxiyo iyo antizagarnoy mar preservative.

Saamaysaa R1-CO-Red2 jidhka

Barashada in xeryahooda yeedhay ketones (kiimikaad, codsiga, Avv, iyo macluumaad kale oo ku saabsan), waxaa lagama maarmaan ah in la ogyahay ee sifooyinka nafleyda maadooyinkaas. In si kale loo dhigo, si ay u ogaadaan sida ay u dhaqmaan on noolaha.

Inkastoo isticmaalka si cadaalad ah soo noqnoqda ee R ₁ -CO-R ₂ in industry ee, waxaa lagama maarmaan ah had iyo jeer in la xasuusto in xeryahooda sida aadka sun ah. Qaar badan oo iyaga ka mid yihiin cudurka kansarka iyo mutagenic.

wakiilada Gaarka ah ay awoodaan in ay keeni cuncun u xub-axaleedka, ilaa gubasho. Alicyclic R ₁ -CO-R ₂ saameyn ku yeelan kara jidhka sida daroogada.

Si kastaba ha ahaatee, ma dhammaan walxaha noocan ah waa waxyeello. Xaqiiqada ah in qaar ka mid ah iyaga ka mid ah waxaa si firfircoon uga qayb-shiid ee noolaha noolaha.

Ketones - deficiency ah xanuunada calaamadihii-shiid carbon iyo insulin gaar ah. In falanqaynta kaadida iyo dhiigga jiritaanka R ₁ -CO-R ₂ muujinaysaa xanuunada kala duwan ee dheefshiidka, oo ay ku jiraan hyperglycemia iyo ketoacidosis.