Ketones: zvemakemikari zvivako uye kutsunga

Organic kemesitiri - sayenzi ndiyo yakaoma zvikuru, asi dzinonakidza. Nekuti yeimwe akafanana zvinhu nenzira yakasiyana kutevedzana nhamba uye kunoita paumbwe zvakasiyana zvinhu zvivako. Ngatikurukurei mukomboni boka carbonyl rinonzi "ketones" (namakemikari ehupfumi, chitarisiko, nzira kwetunhu yavo). Uye kuenzanisa navo zvimwe zvinhu zvakafanana mhando - aldehydes.

ketones

Shoko iri ndiro zita zvakafanana kuti boka makemikari vachiitawo zvinhu, mamorekuru icho carbonyl boka (C = O) kwakabatana maviri kabhoni radicals.

Maererano mamiriro ayo akafanana aldehydes ketones uye carboxylic acids. Zvisinei, vari kamwe mbiri C maatomu (kabhoni kana kabhoni) chokuita C = O. chipo

fomura

The vakawanda payakavakirwa kuti kirasi iyi yeimwe riri sezvinotevera: R ₁ -CO-R _2.

Kuti zvimwe zvinonzwisisika, sezvo mutemo, makanyorwa kuti.

It C = O - iri boka carbonyl. A _{1 uye} R R ₂ - mumwe kabhoni radicals. Panzvimbo yavo angava akasiyana yeimwe, asi rwiyo rwavo vanofanira kuva kabhoni.

Aldehydes uye ketones

Mumuviri makemikari zvivako vemapoka aya zvinhu chaizvo yakafanana mumwe. Nokuda kwechikonzero ichi, vanowanzoororwa vaiona pamwechete.

Chokwadi chokuti aldehydes uyewo ane carbonyl boka iri mamorekuru dzavo. Ivo kunyange ketones pamusoro nzira yakafanana chaizvo. Zvisinei, kana zvinhu C = O kurerekera radicals maviri zvino aldehyde ndiyo chete, panzvimbo yechipiri - rehydrogen atomu: R-CO-H.

Somuenzaniso, kuti nzira mukirasi iyi zvinhu - formaldehyde, kushamise sezvo formalin.

Pachishandiswa nzira CH ₂ O, unoonekwa kuti boka rayo carbonyl haina chokuita nomumwe asi maatomu maviri N.

mumuviri ehupfumi

Tisati kubata makemikari zvivako zviri aldehydes uye ketones, vanofanira kufunga mumuviri vavo zvinhu.

• Ketones - yakaderera kubvunda nezvishoma kana mvura pamwe volatility. Rezasi veboka iri zvakakwana zvazvichanyungudutswa H ₂ O uye vakaita zvakanaka zvinoita zvokufembedzwa.
  Individual Vamiririri (semuenzaniso CH ₃ COCH ₃₎ zvinoshamisa soluble nemvura, uye zvachose chero kukura.
  Kusiyana alcohols uye carboxylic acids, ketones vane chikuru volatility pamwe chete samolecular uremu. Izvi zvinobatsira kuti kutadza kwakaita yeimwe izvi kuti pave chokuita H, sezvo angave H-CO-R.
• Mhando dzakasiyana-siyana aldehydes kunogona kuva siyana States of aggregation. Sezvo yakakwirira R-CO-H - zviri insoluble nezvishoma. Lower - imvura, chikamu iyo yakavhenganiswa yakaisvonaka H ₂ O, asi chete vamwe vacho soluble nemvura, asi hapana zvimwe.
  The nyore kwaiita zvinhu - formic aldehyde - gasi iri chaiyo kunzwa kwakanaka. Izvi zvinhu zvakanaka soluble mu H ₂ O.

The inozivikanwa zvikuru ketones

Kune zvinhu zvakawanda R ₁ -CO-R _{2 Zvisinei,} kuzivikanwa kwavo havana kudaro zvikuru. Izvi anonyanya dimethyl ketone, izvo isu tose sezvo acetone. Uyewo bhururu wake solvent - butanone kana sezvazvakanyorwa zvakanaka haichazonzi - methylethylketone.

Chimwe ketones, zvemakemikari ehupfumi izvo chaizvo kushandiswa mune indasitiri - acetophenone (metilfenilketon). Kusiyana acetone uye butanone, munhuwi zvinofadza chaizvo, izvo Ndokusaka rinoshandiswa perfumery.

Somuenzaniso, cyclohexanone chokuita zvinowanzoitika vamiririri R ₁ -CO-R _2, uye chinonyanya inowanzoshandiswa kugadzirwa zvokufembedzwa.

Tisingatauri diketones. ndozvaari vari R ₁ -CO-R _2, iyo hakuna asi mapoka maviri carbonyl mu murwiyo. Saka, nzira yavo ndiyo: R ₁ -CO-CO-R _2. Chimwe chezvinhu nyore, asi yaiwanzoshandiswa zvokudya indasitiri iri vamiririri diketones, diacetyl (2-3-butanedione).

Izvi zvinhu - rinongova chiduku mazita masayendisiti synthesized ketones (makemikari ehupfumi zvinokurukurwa pazasi). Kutaura zvazviri, pane zvakawanda, asi kwete mafomu ose akawanikwa. The zvakawanda zvinokosha tichifunga kuti vazhinji vavo vari chepfu.

Makemikari ehupfumi pamusoro ketones

Zvinhu zviri muchikwata ichi vanokwanisa sei pamwe chepfu zvakasiyana siyana. Izvi ndizvo yavo chaiyo namakemikari ehupfumi.

• Ketones vanokwanisa vokutoruma H (hydrogenation kuita). Zvisinei, nokuti chibereko ichi kuita zvinoda pamberi catalysts muchimiro emaatomu ezvinhu nickel, cobalt, Cuprum, Platinum, palladium, uye vamwe simbi. Zvaakazoita R ₁ -CO-R ₂ ichishanduka kune yechipiri alcohols.
  Uyewo, kuburikidza kudzorerawo pamberi hydrogenous alkali chesimbi amalgam kana MG glycols vari vakawana kubva ketones.
• Ketones vane dzinenge imwe Alpha-hydrogenic atomu vanowanza kuwira pasi pokudzora keto-enol tautomerization. Zvinonzi catalyzed kwete chete achishandisa acids, asiwo zvinokosha. Kazhinji, asi keto chimiro ndiye itsige pachavo chinonakidza kupfuura enol. zvakanyatsoenzana Izvi zvinoita kuti synthesize ari ketones kuburikidza hydrating alkynes. Hama Kudzikamiswa enol-keto siyana ari conjugation kunotungamirira munhu asi simba acidity R ₁ -CO-R ₂ (kana zvichienzaniswa alkanes).
• Izvi zvinhu zvinogona kupinda maitiro pamwe amoniya. Zvisinei, zvaitika zvishoma nezvishoma.
• Ketones vakaitei nemashoko hydrocyanic acid. Izvi zvinoguma α-oksinitrily, saponification iyo inosimudzira chiitiko α-hydroxyacids.
• Entry kuti sei pamwe alkylmagnesium halides kunotungamirira kuti paumbwe yechipiri alcohols.
• Ndakabatana NaHSO ₃ chinowedzera gidrosulfitnyh (bisulfite) nomukaka. Zvinokosha kuyeuka kuti nezvinoita zvakakora akatevedzana vanokwanisa chete kupinda methyl ketones.
  Kuwedzera ketones, kufanana sei pamwe yavaibvisa hydrosulphite uye zvingaita aldehydes.
  Kana neshungu ane mhinduro kuna NaHCO ₃ (kugocha pasoda) kana chicherwa acid, nomukaka zviri NaHSO ₃ anogona anoora pamwe nokubudiswa vakasununguka ketone.
• Munguva zvakaitwa, R ₁ -CO-R ₂ pamwe NH ₂ OH (hydroxylamine) uye ketoximes vakaumba somunhu byproduct - H ₂ O.
• In Maitiro nechokuita hydrazine vakaumba hydrazones (reshiyo yamarudzi rechirume - 1: 1) kana azines (1: 2).
  Kana wakagamuchira nokuda maitiro chigadzirwa (hydrazone) pasi pokudzora tembiricha vachaita sei pamwe potassium hydroxide, uye N kumira inonyorovesa. Izvi anonzi Kishner kuita.
• Sezvambotaurwa pamusoro, aldehydes uye ketones uye zvemakemikari zvivako uye zvakafanana kugamuchirwa rikurumidze. Saka acetals R ₁ -CO-R ₂ chimiro akaoma kupfuura acetals R-CO-H. Vanoonekwa somugumisiro ketones kuti esters uye orthoformic orthosilicic acid.
• Munharaunda ine dzakakwirira kuwanda alkalis (semuenzaniso, kubudikidza muchidziisa pamwe kuramba H₂SO₄) R ₁ -CO-R ₂ vari pasi ane intermolecular kupera mvura mumuviri kuumbika unsaturated ketones.
• Kana maitiro pamwe R ₁ -CO-R ₂ ine alkali, ketones vanosangana aldol condensation. Somugumisiro, aumba β-keto alcohols anogona kurasikirwa nyore morekuru H ₂ O.
• Quite chinokosha kwemakemikari ehupfumi anozviratidza muna Example ketones acetone vakaita pamwe mesityl oxide. Pakadaro, munhu zvinhu zvitsva rinonzi "phorone".
• Uyewo namakemikari ehupfumi ari makemikari fuma zvinosanganisira Leuckart-Wallach maitiro, izvo zvinoita kuti rutapudzo pakati ketones.

Nokuda kupa R1-CO-R2

Zvaakanga familiarized pamwe ehupfumi of zvinhu zviri mubvunzo, zvinokosha kuziva rakajairika nzira nokuda kwetunhu kwavo.

• Mumwe zvinozivikanwa zvikuru chinja achigadzirira ketones ndiwo alkylation uye acylation Kwezvinonhuhwirira yeimwe pamberi acidic catalysts (AlCl _3, FECI _3, chicherwa acids, oxides, nokuo- nga Exchange Inogadzirwa nemasiridzi anobuda mumiti, uye zvakafanana). Nzira iyi inonzi Friedel-Crafts kuita.
• Ketones vari synthesized ne hydrolysis ketimines uye Vic-diol. Kana yokupedzisira kunoda kuvapo chicherwa asidhi sezvo anowedzera.
• Rinoshandiswawo kubudisa ketones homolog pamusoro acetylene hydration kana sezvazvakanyorwa kunzi - maitiro Kucherov.
• Reactions Guben-Gesha.
• Cyclization Ruzicka yakakodzera kwetunhu tsikloketonov.
• Uyewo, nefuma Data mined kubva tertiary peroksoefirov uchishandisa Kriege rearrangement.
• Pane nzira dzakawanda kwazvo kwetunhu ketones panguva oxidation zvinoitwa yechipiri alcohols. Zvichienderana zvinoshingaira yeimwe vari 4 siyana: Swern Kornblum, Corey-Kim uye Parikh-Doering.

kukura

Wakabata pamwechete zvemakemikari zvivako uye kubudisa ketones vanofanira kuziva apo izvi zvinhu vari kushandiswa.

Sezvataurwa pamusoro apa, vakawanda vavo vari anoshandiswa makemikari indasitiri sezvo zvokufembedzwa nokuda lacquers, enamels, uyewo kugadzirwa Polymers.

Uyezve, dzimwe R ₁ -CO-R ₂ zvakanaka nekusimba sezvo flavorings. Zvazvakadaro, ketones (benzophenone, acetophenone, etc.) zvinoshandiswa perfumery uye kubika.

Uyewo acetophenone kushandiswa senzvimbo chezvinonhuwira kuti pagadzirwe vakarara mapiritsi.

Benzophenone, nokuda kugona kwaro tibatsirwe nemwaranzi zvinokuvadza - vanowanzochema pazvokudya zvizoro uye antizagarnoy panguva imwe chete zvisaora.

Kunochinjawo R1-CO-R2 kuti muviri

Kudzidza kuti yeimwe anonzi ketones (namakemikari ehupfumi, chikumbiro, kwetunhu, uye mamwe mashoko pamusoro pavo), zvinokosha kuti ndinozivana zvipenyu zvechadenga izvi zvinhu. Nemamwe mashoko, kuti muzive kuti chiito zvipenyu.

Pasinei kumbonyanya kakawanda kushandiswa R ₁ -CO-R ₂ ari indasitiri, zvakakodzera nguva dzose kuyeuka kuti yeimwe dzakadaro zvikuru muchetura. Vakawanda vavo vari carcinogenic uye mutagenic.

Special Vamiririri anogona kukonzera akashatirwa kuti mucous membranes, kusvikira kutsva. Alicyclic R ₁ -CO-R ₂ kunogona muviri wakafanana zvinodhaka.

Zvisinei, havasi vose zvinhu kwakadai zvinokuvadza. Chokwadi chokuti vamwe vavo zviri kuitika mune muviri kuti zvipenyu zvipenyu.

Ketones - yakasiyana zviratidzo zvinetso kabhoni muviri uye jekiseni kukanganisika. Ari kuongorora weti uye ropa pamberi R ₁ -CO-R ₂ inoratidza siyana metabolic zvinetso, kusanganisira hyperglycemia uye ketoacidosis.