Ketones: iipropati chemical kunye nokuzimisela

chemistry Organic - inzululwazi inzima kakhulu, kodwa umdla. Ngenxa iikhompawundi ze izinto ezifanayo inombolo ulandelelwano ezahlukeneyo kwaye ikhuthaza ukuyilwa ezahlukeneyo izinto iipropati. Makhe sihlolisise umchiza iqela carbonyl ebizwa ngokuba "ketones" (iipropati imichiza, iimpawu zomzimba, iindlela kuyondelelaniswe sabo). Yaye ezifanisa kunye nezinye izinto ze uhlobo olufanayo - aldehydes.

ketones

Eli gama ligama eqhelekileyo ukuba iklasi wendalo zomgquba kwezinto, iimolekyuli apho iqela carbonyl (C = O) inxulumene radicals zekhabhoni ezimbini.

Ngokutsho isakhiwo yayo efanayo aldehydes ketones kunye asidi carboxylic. Nangona kunjalo, zikhona kwangoko athom C ezimbini (carbon okanye carbon) uqhagamshele C = O.

ifomula

Le ndlela yokubala jikelele le udidi zithako ngolu hlobo lulandelayo: R ₁ -CO-R _2.

Ukwenza uliqonde ngakumbi, njengoko umthetho, kubhaliwe njalo.

It C = O - liqela carbonyl. A ₁ R R ₂ - a radicals carbon. Endaweni yazo ibe iikhompawundi ezahlukeneyo, kodwa ukwakhiwa kwawo kufuneka ibe carbon.

Aldehydes kunye ketones

iimpawu zezi maqela kwezinto Physical kunye yamachiza efana kakhulu omnye komnye. Ngenxa yesi sizathu, badla kubhekwa ndawonye.

Isibakala sokuba aldehydes ziqulathe iqela carbonyl xa iimolekyuli zabo. Bade kunye ketones ze kwifomula efana kakhulu. Noko ke, ukuba izinto C = O incamathele radicals ezimbini ngoko aldehyde mnye kuphela, endaweni yesibini - hydrogen atom: R-CO-H.

Ngokomzekelo, ifomula le iklasi yezinto - formaldehyde, sichukumise nje formalin.

Ngokusekelwe kwi ifomula CH ₂ Owu, kuba wabona ukuba iqela yayo carbonyl sinxulumana mnye kodwa athom ezimbini N.

iipropati ngokomzimba

Phambi kokuba bajongane iimpawu eekhemikhali aldehydes kunye ketones, kufuneka siqwalasele iimpawu zomzimba.

• Ketones - a eziqinileyo ezisezantsi-ukunyibilika okanye ulwelo kunye hexa. Amalungu esezantsi kule klasi zichithakala ngokugqibeleleyo H ₂ O yaye wasabela kakuhle organic izinyibilikisi.
  abameli Individual (umz CH ₃ COCH ₃₎ ngokuphawulekayo enyibilikayo emanzini, kwaye ngokupheleleyo na olinganise.
  Mu kuya kwa nshita alkoholi kunye acids carboxylic, ketones kuba ukungabikho kozinzo olukhulu kunye ubunzima efanayo eziphilayo. Oku kunegalelo ukungakwazi ezi zihlanganisi ukwenza uqhagamshelwano ne-H, njengoko kusenokuba H-CO-R.
• Iintlobo ngeentlobo aldehydes banokuba States ezahlukeneyo udibaniso. Ekubeni ephakamileyo R-CO-H - oko eziqinileyo ezingenakunyibilika. Lower - ulwelo, inxalenye yayo oluxutywe H entle ₂ Owu, kodwa ezinye zazo enyibilikayo emanzini, kodwa akukho ngaphezulu.
  Elula olu hlobo kwezinto - aldehyde formic - igesi apho ivumba bokuhlala ivuza. Le nto enyibilikayo kakuhle H ₂ O.

Le ketones ezininzi ezaziwayo-kakuhle

Kukho izinto ezininzi R _{1 -CO-R-2,} ke, kakuhle, nokwazeka kwayo kubo abakho kakhulu. Oku ngokuyintloko dimethyl ketone, ezingamaziyo sonke thina acetone. Kwakhona asebenza yakhe nesinyibilikisi - butanone okanye njengoko kubhaliwe Ubizwa ngokufanelekileyo - methylethylketone.

Phakathi kwezinye ketones, iipropati yemichiza ezisetyenziswa ngokubanzi kushishino - acetophenone (metilfenilketon). Ngokungafaniyo acetone kunye butanone, ivumba mnandi kakhulu, nto ke leyo ebangele isetyenziswa iziqholo.

Umzekelo, cyclohexanone inxulumene abameli ezithile R _{1 -CO-R-2,} kwaye amaninzi kusetyenziswa ekuvelisweni izinyibilikisi.

Singasathethi ke diketones. Loo sengoma R _{1 -CO-R-2,} apho akukho namnye kodwa amaqela amabini carbonyl kwi ekwakhiweni. Ngenxa yoko, ifomula yabo: R ₁ -CO-CO-R _2. Enye yezona alula, kodwa ezisetyenziswa kushishino ukutya kukuba abameli diketones, diacetyl (2,3-butanedione).

Ezi izinto - yinto uluhlu nje encinane izazinzulu kuhlelwe ketones (iimpawu yemichiza kuxoxwa ngezantsi). Enyanisweni, kukho ngakumbi, kodwa hayi zonke izicelo Ayifumaneki. I ngaphezulu kubalulekile ucinga ukuba abaninzi kubo ayityhefu.

Iimpawu lwemichiza ketones

Substances yale udidi bayakwazi azithethelele izinto ezahlukeneyo. Le nto na iimpawu zazo lwekhemikhali okhethekileyo.

• Ketones bayakwazi zincamathele kwi H (hydrogenation reaction). Nangona kunjalo, kuba imveliso yalo yokusabela kufuna ubukho ehlanganisa ngohlobo athom ezibengezelayo nickel, ayibe, Cuprum, platinum, mbala, kunye nabanye. Reaction R ₁ -CO-R ₂ nokuguquguquka ukuya alkoholi eziziisekondari.
  Kwakhona, ngokuhlanganisa phambi a hydrogenous kwealkali amalgam metal okanye glycols MG lufumaneka ketones.
• Ketones ukuba ubuncinane omnye atom alpha-hydrogenic bakholisa kuwa phantsi kwempembelelo nee-enol tautomerization. It is catalyzed kuphela ngokusebenzisa asidi, kodwa ezisisiseko. Ngokuqhelekileyo, ifomu nee na isenzeko ozinzileyo ngakumbi kunokuba enol. Le lizama kwenza kube lula ukuba nokulungelelanisa le ketones ngokuthi hydrating alkynes. Iifom Ukuzinziswa enol-nee Relative le conjugation kukhokelela ubumuncu kunokuba strong R ₁ -CO-R ₂ (xa kuthelekiswa alkanes).
• Ezi zinto zinobungozi ukungena sokungamelani kunye ammonia. Noko ke, kwenzeka ngokucothayo kakhulu.
• Ketones azithethelele hydrocyanic acid. Oku kuzisa α-oksinitrily, saponification leyo ekhuthaza nasisihlo α-hydroxyacids.
• Iphetshana azithethelele halides alkylmagnesium kukhokelela ukuyilwa alkoholi eziziisekondari.
• Ukujoyina NaHSO ₃ kwenza ukuba gidrosulfitnyh (bisulfite) yezabelo. Kuhle ukukhumbula ukuba indlela kolu thotho okunamafutha bakwazi ukungena ketones methyl kuphela.
  Ukongeza ketones, ezifana kuphendula sodium hydrosulphite kwaye kungenzeka aldehydes.
  Xa itshiswe ngeqondo kunye nesisombululo NaHCO ₃ (yesoda yokubhaka) okanye acid bezimbiwa, avela ka NaHSO ₃ cazulula sikhatshwe kokukhutshwa ketone free.
• Ngexesha reaction, R ₁ -CO-R ₂ ne H. ₂ OH (hydroxylamine) kunye ketoximes, njengoko eceleni - H ₂ O.
• Xa ngayo ebandakanya hydrazine kuyilwa hydrazones (ratio wenkqu edityanisiweyo - 1: 1) okanye gazini (1: 2).
  Ukuba ufumene ngenxa imveliso awasabela ngayo (hydrazone) phantsi kwempembelelo lobushushu iza kuphendula potassium hayidroksayidi, kwaye N ume zigcwele. Le nkqubo ibizwa ngokuba Kishner basabela.
• Njengoko sele kukhankanyiwe ngentla apha, aldehydes kunye ketones kunye neempawu imichiza kwaye inkqubo ukwamkelwa efanayo. Utsho acetals R ₁ -CO-R ₂ ifom entsonkothileyo ngaphezu acetals R-CO-H. Babonakala ngenxa ketones ukuba esters kunye orthosilicic acid orthoformic.
• Xa environments ezixinene of alkalis (umz, ngokufudumeza kunye H₂SO₄ wamandla) R ₁ -CO-R ₂ ziphantsi i emzimbeni aphakathi ukwenza ketones ezihluthiyo.
• Ukuba yokusabela nge R ₁ -CO-R ₂ iqulethe kwealkali, ketones baye aldol amafu. Ngenxa yoko, i-alkoholi β-nee kwakheka enokuthi lula molecule H ₂ O.
• Lidla iipropati yemichiza ebalulekileyo azibonakalisa Example ketones acetone awasabela ngayo kunye mesityl oxide. Kwimeko ezinjalo, impahla omtsha obizwa "phorone".
• Kwakhona iimpawu eekhemikhali into ephilayo ziquka Leuckart-Wallach reaction, nto leyo inegalelo Ukwehla ketones.

Ngenxa ukunika R1-CO-R2

Ekubeni ngomsebenzi iimpawu izinto ekuthethwa, kuyimfuneko ukwazi iindlela zixhaphakileyo ezwi yabo.

• Enye abasabela ezininzi ezaziwayo-kakuhle ukulungiselela ketones na alkylation kunye acylation le khompawundi enuka phambi ehlanganisa emuncu (AlCl _3, FeCI _3, acids izimbiwa, oxides, nentlaka zesiqinisekiso wotshintshiselwano, kunye like). Le ndlela yaziwa ngokuba Friedel-wezandla basabela.
• Ketones ukuba kuhlelwe yi ketimines haydrolisis kunye Vic-diol. Kwimeko ye yokugqibela kufuna ubukho acid izimbiwa njengesixhobo.
• Kwakhona kusetyenziswa ukuvelisa ketones homolog ukuxovwa iasithilini okanye njengoko ibizwa - basabela Kucherov.
• Ukusabela Guben-Gesha.
• Cyclization Ruzicka ezifanelekileyo ezwi tsikloketonov.
• Kwakhona, i-data into geni evela peroksoefirov ephakamileyo usebenzisa Kriege ngokutsha.
• Kukho iindlela ezininzi ukuze Yindibanisela ketones ngexesha ngayo igcwala ye-alkoholi eziziisekondari. Kuxhomekeka imichiza esebenzayo ezi-4 reactions: Swern Kornblum, Corey-Kim kunye Parikh-Doering.

scope

Ukuba iyitshinizele kunye iipropati imichiza kwaye bavelisa ketones kufuneka wazi apho ezi izinto nazo kusetyenziswa.

Njengoko kukhankanyiwe ngasentla, inkoliso yabo esetyenziswa kwishishini kwemichiza njengoko izinyibilikisi for lacquers, enamels, kwakunye ekuvelisweni neeplastikhi.

Ukongeza, ezinye R ₁ -CO-R ₂ ukuzabalaza kanye njengayo. Ngenxa yoko, ketones (benzophenone, acetophenone, njalo njalo) zisetyenziswa xa iziqholo nokupheka.

Kwakhona acetophenone kusetyenziswa icandelo imveliso ipilisi zokulala.

Benzophenone, ngenxa ukukwazi layo lokunciphisa imitha yingozi - wesithako eqhelekileyo zokuthambisa kunye antizagarnoy ngaxeshanye ukubola.

Ephembelela R1-CO-R2 ukuba umzimba

Ukufunda ukuba iikhompawundi ekuthiwa ketones (iipropati imichiza, isicelo, kuyondelelaniswe, kunye nezinye iinkcukacha ngazo), kuyimfuneko ukuba aqhelane iimpawu ngokobugcisa kwezi zinto na. Ngamanye amazwi, ukuba uyazi indlela abenza ngayo izinto eziphilayo.

Nangona nokusetyenziswa rhoqo R ₁ -CO-R ₂ kushishino, kuyimfuneko kusoloko ukuba ukukhumbula ukuba ezi zihlanganisi ayityhefu kakhulu. Uninzi lwabo umhlaza kunye mutagenic.

abameli ezizodwa bayakwazi ukuba kubangele ubuhlungu ukuba inwebu yangaphakathi, de liphele. Alicyclic R ₁ -CO-R ₂ zingachaphazela umzimba ngathi iziyobisi.

Noko ke, asingabo bonke imithi olu hlobo kuyingozi. Isibakala sokuba abanye babo ngokufanelekileyo inxaxheba nethe eziphilayo eziphilayo.

Ketones - a unique iimpawu iingxaki carbon ukutya kunye insulin ukuswela. Ekuhlalutyeni umchamo negazi phambi R ₁ -CO-R ₂ libonisa zezigulo ezahlukeneyo pathways, kuquka hyperglycemia kunye ketoacidosis.