А.Н. Кост, Р.С. Сагитуллин, А.П. Терентьев - Упражнения и задачи по органической химии (1125895), страница 38
Текст из файла (страница 38)
9. 6 . 9. 12.e) Cyl<.lUIH8T 9TnJleRrJlIIKonl!1II) .!lHaMHA SlHTapHoil KHCJl OTlilj0) 9THJlOBblA S¢I1 P unaHYKcycuoll KHCJlOTbI.H30Il POlllIJlI!HTO pHall KHCJ1OT8..!l) nponaHTeTpaKap(50RoBbl i"t s<imp (noc:ne rHAPOllHS8nOJlyqaeTC IJ rJlYTapoaali KIJCJlOTa).C H 2 (COOHhII AeKapOOKCIlJlnpORaflllRCH ~(COO~H &)t ..... CH(COOC,H.},Na .....-..... (C.H500C) 2C HCH(COOC2H.h ..... (I:WOC).CLIGH(COOH )~ .....to--. CH 3 COCH3CHtCOOH_I/0-+ CH:;COO NH. -+ CH aCONH 2CH zCOOH,CHs(CH2)6CH20COCf'!3 (It·renTIlJlOBblH 9(llHP YKcycaoll KnC.IIOTbl).6) IlCn OJlb30BaTb n eperpyonllp OBKy r O<j>MBlla .JI) ,Mll n OJlY'leHlul I1poMelKYTOtlHOro J.\HMeTIIJl3TlmKap 61111OJl aHCOOJlb3YiirepeaKlllfJO f plJllbllpa (.IleHCTBlIe 3TIl.QMarIlHli 6pOMII){a lIa 9TIlJlaueTaT) .MOlKHO ,neplI!puuHpOnBTh KUCJlOTY II 3aTeM OKHClIlITb ee .1\0 aue.ToYKc YCllOros<jll1 pa.
npn KI1CJlOTHOM pacruenJleH ll11 nOCJle)lHero a) Bbl.!lMRlOU\ allcli ,llBYOKRCbyr.nep oM aRTHBllall (TOr.!la MeTKa 6b1J1B B r pyun e C OOH ) 11J111 6) al<THBelInO.'lY'laloU\HlicJI aueTOH . nOCJleJUlIItl pacU\enJilleTCll 6POMOM B l.I1eJlolJlloii cpe,lJ.enpl!'leM uonytl8eTcll a) aKTIIBHblil CHBr:, (TOr.!lB MeTKa 6h1J1a R r pynne CHsJI[f CH 2 ) IfJIll 6) neaKTIlllHblli CHBr s MeTI(a B r p y nn e CHOH I1CXO,llIlOro BemeCTBa) .
LJ To(\h1 pa3l1HQBTb MeTKY B CHa H CH ~ nOTpe6yerc II W!a4aJle C-aJlKJ1Jlll POBB Tb aueroyKcyCHblli !Hllllp.M O}{{HO T8KJKe H3 ~ - OKCHMBC.q llHOi! rotCJlOTbI nOJlY 11IITb 8MJI,ll If npOBeCTI!neperpyn m lpoBKy ro cjlM811 a (eCJIu BbI.!le.nlleTCSl aKTlfJIHblii CO~, TO MeTKa (lbl.JID B rp ynne COOH). nonY'lCtlffbl H OKClf3MI1H OKHCJlHTb 110 MOJIO'lHOIi KnCJTO.TbJ , a ee .l\eKapOOKCHJlnpOBa Tb (KOllTPOJIb 3KTHBH OCTH 1Ib\,lJ.€JII! IOmerOCl! CO )2H T .
.11. coe.!llUleHl1ll, pearJlpYIOU!er O C KapOOHBTOM Harplll!, BOSMOlKlIO CTpOeRl!eIIJllI (CHJ) 2CHCOOH . Bropoe COe){)lHelllJe - CJ! OlKR.bJil9¢llp CH8COO~Hb'Coe.qlfHeHl!e CeHaO MOlK eT CihJ Tb CllJ!pTOM IJJlII npOCTbltd 3lj>JqlOM. Cnoco61l0CThpeam pOBaTh C H8Tpl1eM AOKa3blBaeT, 410 !ITO emlpT. PaCCMOTpeHue llpOA)'K'TOB OKHCJleHJlIJ AaeT M il Hero ¢opMyJly (CH shCHCHCH 2CHCO-I --c6~CH 2CH29 .20.a) M8J10H08ble KHCJlOTbI neroIUlKJIHlJeCKUe aRrRJrp" Abl.9 .23.C H aCH( COOH )~to.CH 2-COI~NHCH~-CO.n.eKap(50KcHmtpylOTCSjHERACbll1.(EHHblE (UEnPEUEJTbHI.lE) O,IJ;BO· UInICJIOTbl n HX npOHSBO,IOlD1E10 .1.B)CH 2 =C-COOHP)lIHT8pHble -06pasylOTAlJYXOCBOBBIdECH, = CH-CH,-CH,- COOHICH., a) CH~-C-COOH~)"CHj-C-COOHH-G.-COOCH3 CH~OOC-C -H"n ) CH 2OCO( CHthCH=CH(CH~)7CH3blOCO(Cll~hCll=CH(CH,hCH81l.1116H194L9KCTPaJ<T Bbl.CH 3CH 2CI-I~COOH8.94.y)CH,CO NHNH t,-C..O9.
17 .(C H SCOO)2Ca(9cj)Rp)I ) CO, ..... (CH4)§CHCHCH~CH8 - _ ICHa).CHCHCHtCHaI2) HOIIMgBrCOOH 9.1. 0)o+ Ca(OH) 2 -~CH~-COCH aC H =CHCH 3 -+ 2CH 3COO H2CH.COOHMI/ (CHahCHCHCH!CH u rocjJ .8.68. P aCTBOpllTb CMeCb n 9Ijlllpe, H3BJle'lb MaCJl llHylO KIlCJlOTY paC.TBOpOM 6uKap6oHa.8.74.~)I-J )j M OJKHO T8 KJKe . CHsMg !C(OC 2H fi8 .40.
8) 9Tep'·!(jJIUGlUnlJ B npHcyrcTBillJ HC , H 2 S04 , BFa B Ka'lecrae K<lT8JIHaaTOpoB;6) C nOMOU\blO I1lla30MeTana liJllI 4epea cepe6pIDlYJO conb; B) 9Tepn¢f1Kau.HII II OP1!CyrcTBJlII BF 3 B KaqeCTBe K8TaJlll38TOpa (H C I [1m, H SO,2MoryT npHcoe,QIHIIITbCll no ,Qllofmoft CBllan);r) KIITIllyeH [le H- npOlUlJlOBOro a¢u pa C 1l36blTKOM MeT81l0Jla, COAepJKaU\ero3 % cepHol! KHCJlOT bl.8.43. HC CH - CHaCHO _ CA BCOOC 2 Ho8.47 . 8) STHJlOllblfi cnllpT. H30a MIIJIOBbiA cmrpT, an eTa T lIaTplIlL8.50. 111 ,2 ~ II~OBMI! P Il2" OBOJ1 KlIC.nOTbI Ii 95,9 il U30aMl1J10BOrO collpra .CIIRTe30M~HBr\CH ~OCO(CH~),CH=CH(CH~),CHlI10 .2.J7*B)A)e)R)oil)AlIMeTHJl!\JYMapOB<l II KlICJlOTa; M ~ T HJl}JeTaKpIIJlaT; 6HHHJlOBblfl SlImp KPOTOIfOBOA KHCJlOTbl: HMIlA \IaJlel!Hoaoii KIICJlOTbl; 9THlIOBblil 9<f>rlP OJIeHHOBOli (quc·) IIJr1I 9JI aIIJ.lIlHOBOii(m 1)(1 He·J KlIcJI OTbI • 19510.5.
6) BrlllHnyKcycHBH Klicn ora nOA ileiic TB lieM llte.ij0411 OTlfaCTIi 1l30\lepH3ye r cSI 8" POTOIIOBYIO; B) HOOC -C=C-COOH.rHAPOKCIiJ13 BTaKye-r 6eTB· n o.~ OiKeHlle 140 JleK)'nhl BKPHJl.OIIU Tpu.ij a , a 33reM npllcoeAIl HHeTcllnpOTOH. n onY'Iae TclIHOCI-l 2C H 2CN. rp y nna HO ROTOPOI'O ClloeB npllcOe,llIlUSleT nTOpylO MMe.KyJly BK PIIJlOI·III1'pHJla. oCipa3ySl .l\HUll aHl\1l3TJfJlOBblir 9(jmp O(CHzCH:CN)l'B KHCJl bl X Cpe.l\3X DIIB!{Me npoTOHllpyBTCJI HH TpfWbliaSl TpynnB II 06pa 30.BalllillJi1cSl HlnplI.!lllli -KBnIOH npl1COe.llnHlleT rHJlpOKCllJI, 'ITO npllBOJUI r (nocJJe IIJOMepU33UHH) K 06ps30BaHHlo BKPUJlBMII.I\B. B tiMee )to.BCTKHX yC./lO.RlJSlX n tJlPonH3 If.l\CT .1\0 BKpHJJOBOfi IWCJlOTLI. lie JBTpar l1 Basr JlBOliHYIOClur 3b yrnepoA- yrMpoA;If) )1lfCIIODbili CHHre3 (pea KU II n .llUJlbCa - AnbJlepa) C 06p a30B8HlleM BMJI,!la3.4 - .IUIMeTIIJlqHKn OreKceR-3-KBP6(lHOBOii KIlCJIOTbi .Y mpalic- H30MepB KOHCTBRTB cnlitl - Cn llHOlloro A3811 MO.l.leiICTBlIsr .Q,.I\lI Bil.IIHJ1bllhl X n pOTollos :.na'IlITenbAO 6 MLw e, lleM y /{Uc-H30MepB .J.1cnon b3Ylhe, HanpJlMep , TO, 'ITO Y HenpeAeJlbllbiX COe.l\lUlellllU xap aKTep lIb1e lJaCTOThI J\1l0ii HO/! CBIl3H y rnepoll- yrJle poA 11MelOTcsr B H K.cneKTjle..OJleIHIOBasr ( IIJl II 3Jlall.lVfHoBBsr) KIICJlOTa10.23.
A)10.24.10.25.10.27 .B) H O C I-12 CH-CH 2CO OHIrJCI-l"3)II • IO-C{}-cHC!-I 2CH36) KpoTOlioBasr KIICnO'l'a ;B) CH~Cl-l2CHCH eClInooT'KanponaK'fOH~II .IB. a) HBTplleaall COJlb MO.1011HOil KnCJJOTbii6) n8TpHeoafl COJlb ex-3ToKclmponllolloBofi KllcnOTbl .11.20. CHS(Cl-l2)uCH(OH)COOH -+ CH3(CHt>uCI-IOHooOH+npn 6o.nee MHrKOM lIarpeBaHlIll no.nY'IaeTcsr JlaKTIU\.OKC.UKIICJJOTbJ nMYlJac.'TC!I CMeCb ~uc· II mpaNc - R90MepoBTlITeJI bHee m paNC -ll::IOMep B e ,e -KoHtPoPIIIBwm.06llta H ljJop Myna CIlH2n_20~.
npH 1l= 1 JlaKTOHY OTBeliaeT tjJopMYJl a CO~ . Co.·rneTCTBeHHO H O -COOH , T. e. yroJl bliBH KHCJlOTB - IIYJleBofr !{JIell pH.ll.aOKCHKJlCJ10T.HOC) KeN12 . t.B) IJOOCCHO 12 .2.B) ..,· I(eTOllanepH8110sall JOICJJo'fa, JlesYJlmlOS811 I<IlCJlOTa; e) Menl.llOBbJ il 3{I)IIp ~ - MeTOKCRKpOTC II 0 sdi KIICJJOTbI; K) 6pOMIIIYKoea S! KllenOTB (T. e. ex , ~ - J1.116pO!\l - ~ - ¢op~mJlaKp I IJl OB all ): II) :3 , 3. 4-TpItMeTI1J1 - 5-01(COr eKCBnonaH KItCnOT8.
6) IIMeeTCIl OBIlJlY 3THJlOBbl ii 9¢"p ex .MeT".1aueTO YKcYCHOli t<1fCJlOTbi.a) CH 3 COCOOHB) C H a(CH2)8C OCH~ COO H ill HOOCCH 2 CH i C HCOOII ~OCHa12 .3.I VI.r) CH 3 OCll=C(ooOCQH.)-+ H - C - CH(COOllh -+ 1/ 2H.O ..... CH 3-CH (OH)-CH 2 -CN - --+ CHs-CH (OH) - CHa-COOH c1-1+) -+ H -C-CH 2COOH ..... CO,C !-J uC H ~C(lOH .....
(CH 3CH 2COOhCa .....Ioor) 06pasyeTcli12.8.C~H~IC2HaCH;lC H ~COC t - -+ CH sCH~COCN _{HJ 11 ilL196"'R,O-+(H+)-+ CHaCH,COCOOH -.. CH 3 GI J ~CH (O H)COOHHeo6xoJ\IlMO yq , eTl> , 'ITO OTlltenn-ellne HHa I 1t,lleT npeADo411lrenhRo KBKmpaNc 3J1IlMlIIlllpODaJlHe .B) rpy nna 011 B IIJIbqlB - nOJJ.OlKeHIlIl 3aMelltaeTCfl ua 6POM;JI) aUE'TaJU.o.QerllJ.\ 1\ M}"paSbll1l3sr KllCJlOT8.II(~)-OC'"'..... CH aCH 2 C(OH) C OOH11.15.+ CHaCHO II ..... Cll aC H , COCH 2 C H s ..... CH 3C H 2C( OH)CN .....KCN onnllieCIU! ne,lleflTeJlbHolI(tle.nBSlTe.1bElblx) .
n peA/loq.11 .23. CH 3CI 12CH(OH)CO OH11.13 . a) CH . -CH=CH!! --+ CH~-CH (O I-l)-CH2C I _-+r) HanpJIMep,M:ICH aOCH 2CH 2COOHB) "( -OKCHMaCJllrHBsr KIICJlOTa;t') A11 3THJl OBbIH 3(~llP rJl IIKMeBOJi KllcnOTbI ;IK) MeTI1.ijOBblii 3qJJJP tl-aUeTOKCHnponJloHoBoij KHCJlOTbl; K) ,,(-OKCIfKPOToHoBasr KIlCJl OTa; JI) T- 6YTllponaK10H 8)Mil 5-3T11n,!.ypaIlH.llOH-2.l2.
AJThJJ,ErII,!I.Ortl1CJlOTbl Jl ICETOKHCJJOTbl. IiETO·EnO.lJbllAflTAYTO:\IEPUJI . CHUTE3bl C All,ETOYKCYCRbIM 3(l)IIPOMOHCH s1\ . 5 .,QJl!ITHJl r nlll(OJnlJl (nBKTlID,).\CHo-CH-COOHClA) CH sCH 2C(OH)COOH11 . 2I11 25. (CH a hC HC J-l (OH) CH ~COO l1II. OKCDKUCJJOTLIII. I.".17 . a) GH aCH 2CH - CO-OII e) B llteJl04 HWX YCJl OnflSlX HOll12.10 . H.l.leT 811YTPIIlIlOJleKYJlflpilBli UlIKJlII38lUI1ioII/'JHl)"cOOCHsAIIo6ps3yeTcSI9¢IIP AHCI (ras)CHaCOCH 2CH2CHO + 2C 2HDOH - - - +12 . 11.A) HaTP uAau.eroYKCYCHblll ~IIP MOlKllO aJIKlIJl HPOB8n.. RanpnMep 9<jlIlPOM ~·ra.JlOreHnpomWH080A KHCJlOTbI, a 38TeM "POsecTH KHCJlOTIlOe paClll.enJleHHe .MOlKMo nO,l\eliCTBODaTb 1I0110M lola H3TpHHalleroyucycRblil 9c1>IiP II npoBecTHT3Koe me pacUl.enJleRoe.NaOOI- CH3CO CHtCH.CH (O~H6)~ _ - +(H.O)C.II,ON"HCI12 .23.- HOOCCH sCH.Cl-l(OCaB6)z - - HOOCCHtCH.CHO(H.O)12.12.a)CHaCOCH~ooOC2Ha (CH.laCHI8) MeTflJl9TI1 Jl KeTOHCHuCOCI-lCOOC zl 16ICH a12.18 .,I\) CH sCOCH,CH2 COOH+ N H~NH?HtC_H.~C::.H.ONo~HCA., I_->CoH.()/'IaCH sCOCHCOOC2 Hr.
--~ C H "COCNaCOOCtll~ ICB) CeH,OOCCHOCoe,lUlHeJtHfl a), B), .1\) II e ).s) CH aooCBr zCOOC t H6 (KOHeQBhlIi npOA)'K'I'):H) CHs-C---CH?12 .15.12.17./Ib_ICH ~COCCOOC ~H~b12. 18. Am<OJ'OJlllT-8HHOH BYKJleOlfJHJJbHO 8TaKyeT aTOM yrJJE~p01l8 Kap63T OKc lirpyn n I.)'ITO nplfBOllHT (06p8THMo) K nepe3Tepn<jlnKa ll JlI1NnOH ·12. 19. 8) CH aCOCHCOOC zH6 - - + CH 3CH COONazI+ CH COONa + C H 0 l-l3213. YT JIEDOllblI/ OHC6I12.21. 6) JleByJl liHonal! KHCIIOTa , 8UeTOHflJlalleTOH.12.22. 8) CHaCOCH2C()()4H&CoB,ONa-- -+CoH.
I II) NsOHCH COCHCOOC 2 H&IC2H.HO-C-HJ-l-C-OHCH 3COC HNaCOOC~H& _.) HtS<>.CtH,CH 2 COOH-+Keror pynnyCH.1CoH.ONa --.- -+ CH~COCH COOC2HIHCXOAHoro ae ~eCTB8n 38TeM nposecTIICH nCOCHNaCOOCt H6 -+C.A.ON"-C HJCOCNaC~Hb-+ICHaICII ,,-CotCOOCtHo ICH s198IH C-OHHOIC-HH- t -OHNaOHH- C/ I(OHU,) (CHahCHCOOHOHICH"OHr JlIOKOH081U<.C) ICJlOTiI0H-1 0HI.IH-?- Ol lCH i -~ '4>pyltTO!I~13.4.IC H~-+HO-~:jlCH20HooOHCH3-1/°11r- tWYKl'OSaCH aCOCH1 COOC2 H6CH.IB-2I(KOII l\)Cl1nOllCH20 H13 .3 .CH 36)lI-tCI )a+H"'O)f{BO T3K'lKe BOCCTaH08l1'1brB)l.j) OJIIIB .H,O- _ CH:,COCH(Cl-i 8 he) ):IerlCTeBe flo,l\a us HaTpllfi au.eTOYKCYClII,j1l ~HP C IIOCJle.u.YIO UJ;nM MI.u.pOJIHTalJeCKHM paCw.eUJleHHeM;H) aueT oYKcycHblll 9¢lffj>OKHCb 9TIIJleBa C OOCJJe,l\YIOII.\ItM KeTOHHblN pac.w.enJleHHeM ."N/~O-CH 3CH 3C1I ,1C3ICHs IN(Hell6) CH sCOCH 2COOC 2 1lh --~ CH ~ICOCHNaCOO~H 5 ,,/12.14.H,O-+ CH ~.COCH~CH(CH3)'-CH(CHahd~\--+ Cll sCOCl-INaCOGCzl-l& H -t--OHII0IIHO-C-HH- CIIJ- C-OHICH,PHl·naKTOJle#0t-0H- t-OllHo- LHI0II-I- C-OIIH- tICH~OH6· JlJ!KTOH19913.8.CH "OH1CO13 .
II .¢PYKT038.13.2.CHO6-10H1HO-G-HH-~-OH +3NH!NHCe H& -+ C,H 6 NH, of NH~(CHOHh~H!Oll111-C-OHCH 20 H(GB,COO ),FeH/HI~ 1C= NNHCoH6HO-C-HI1...H-C-OH(CHOH)3~H10HIIH.O\--H,o CHOll - 1HeltHOll 1ICH~OHCH, OHCH 20li1;--c=oH-C-OI-i1H-C-OH1\UH-C-Ol-!hH 0 H03330H0301i\0Nd/HgIHOHClieOH- -CHOllt HOI-I-I 112- -CHCHOb1011dl-JOH\1-- \~1101i- - CHINOH//C-I-!a)aiOH CHOH11BO--C-II1CHOH--+ CHOH -CHOIla)CooHIHeN-1~!10HCN\ClIOHC=O1(tHOHh2C"HIS.3.CHO-+ 1tH 0H.. .C= NNHCftH, 13.9.(CHOHho1/H,O,--- IIi,O~O&01-1Br,I+ HtO +COOHCOOHCHOHbiOH\CH~OHICHPHCH.OHICHOHNH2 0 H-- ....K03l1 il IIMeeTICHOHC("HICH 2 0H!-iNO.ICHOHKOIIl( .CH 2 0li6)ICHOll1ICHOII--.-CI-I 2 0HOOpa30naHHe Tp HMeTOKCU fJrYT8poooA KlICJlOTbi nOKa3b1eaeT.CHOH#0CHOH13.18 1Na /H gdHOH1CJlOIlI.
CH20HnJCOOI-IdHO HdrroH~HOCH3)(CHOHh\1--cHIb·I~OHMt:'THJJroJlOKT03lQlB)410IfCXO)Ulbl~fJflOCTpOl!Alle . ~I IOCH .(CH. ), SO.-I NaOH)ICllOH0(CHOCHahI1__ cHHC!-(H,O)-tH,OCH Je OOHTPIIOI< C'_lI r ./l)'T af)OoaHKlfCiIOTSI~HOH_ 0\CHOCHs). l -dHCOOH liNO,--+(~HOCH8)s1COOl-!1CH 20CH 3n eJlTlrrl;i . IO.1. 5- OKIIClloeCH,OCOCI-I sTp".eTOKC:llrnyr3llOBfUItUiC.J]QT~ICH .COO-C- - - _vICH oCOO-?- H Ii-C-OCOCH JH-~-OCOCI-l36-'2- - 20010I°I"HCooNa13 .20 .
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