А.Н. Кост, Р.С. Сагитуллин, А.П. Терентьев - Упражнения и задачи по органической химии (1125895), страница 37
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J. 7; 2837)MeTlIJl-6mOp - Ciy-rHJlOllLl ii 3cjlllP ; 5-)1.ITMen IJl-4 , 4- )l.H3TUJlret(C aH .!UJOn- 2 ,:3;6. 10_ (CHBhC HCH ~CH~(CI'I~CH C H2CHn)~CH2C=CHC H 20HIICH l8.13.r)CMecbCH 3C( CH shCH:CH(OH)CH 2CH:l 6.14.4·MeTIfJIDenTel-l-l 11JI1I 4-MeTH.~neHTeH- 2 (B nO)106HOM ('.1I'YLJae o,nROBpeMeH HO llony qaeTCB if30MepHhIli 9T1lJ1 H30 npOllllJl K a p6HHo .'I) ,6_16 .It)188B).I1JllOOqpollIIJlK3p6miOlijICH20H0.4 1.r) CMecbCHOICHO2.4-AilMeTIIJlneHT3HOJI ·3.COOHICH 20HCOOHICHOCH;sCH =CCH lICIl 2CH sCH 3CH~C(CHshCH(OH) C J-I2C1i2Cl -l~ IIBOCCTa HOIlJIeHReMMeTlM3TIWxeTOH3.C On'TII 'leClm Jl,eHTe.1JbH bThl OCflOBaHlleM ( H3 11 pIIMep.
6pYl\ JJj lOM IW ll l\Il HXOHHHOM).pa3,D,eJUIIOT )l.1I3CTepeOMephl KPllCTM!1I1133IUlefi II '3areM J1I)1.po.1J1l3yKlT.A. E _ Ap6y30B nOK33 M . 'ITO MeT3 IIOn ot'ipaayeT 'l'pIIMe Tlm¢oc$a T. T. e.(CH 3 0 )aP . BYT3HOJI n p e.D.nO'ml TeJIb HO ,/IaeT <4HeCI.a) oJn a)1.eUIfJlOBbu'I cmlp T o6pat'i3ThlBalOT XJlOPIfCTbIM 'I'HOHHnOM 1\ lLlt'ibJTOK eroy ,nanHlOT ynapllBal!HeM B BaICYYMe. J\\OlKHO llcno..1h30BaTb PCI~ II o6paaylOlulmCJI POC l s TllI(lKe Y)l.2JI!lTh Q'r roHKo» B B3J<YYMe;0) COOT BeTCTB YlOlluni a~IHJlOll."rn cmi p-r BCTPRXIIB310T C KOIIUel-lTpHpOaalluoll CO'JlHHOH IOIC.ryOTO H a )l,eJ1llTeJlhHOil Bo pollKe. Bep xHlIH CJloii OT .D.eJl mOT, npVMh!B3lOT BO)l.oii.
CYlllar xnopliCTblM K8JlbUHeM II nepe rO ll SilOT;B) n e1lT 31l0.ij -2 oi5pa 6 aTblB 3loT PBrs;r ) rel(Clr.'lOllbrH cnnpr flarpen aloT C 1I0)l.HCTOBO,llOPO)l.HOil KHcn OloiL6. 39. CHO2, 3 - 3noKClIOY T8H •nOJl)"IIITbMOlKHOJIJIlI p a3)1.e.nemI H paueM3Ta er o n epeBO)lllT B 1<FICJlbIl1 cynb¢aT. nWlY4alOT COJlb6.34 .I2) H,O6.26. PaueMHLJeCKHH c nllp-rCHoOCH 36 .2.CH aCH 2MgI - - -. CH sCH zCH 2 0 H-CH 3COORI.npH CH3CH ~C=CH CH~CH8IICHs6.42.IICOOHCHs6) (CI 13 bC=CHCH zCH(CH 3 hB) (Cl-q:\C=CHCH2C!-{20H r) CH3C ll~COOH+ O= C(CHsh(BHa1.JaJleJl,erll.D.p3TIlUII'H11.0CH;jCH 2 CH = C(CH s)t)1896.46. (CH;I)2CHCHzMgBr8)I) (CH,),CO---+2) H,Or)- u.O~ (CH3hCHCH ~C(CH 3hOH - - +k fit(CH 3 ).
CHCH=C(Cllah6) CH ~CH 1CH CH~ -+ CH uCH 2COCH n -+ bHC[I.C\lJ CH.MgB~ CHJCH2C(O!-! )CH~CH~CHg 2)H,O6.63. (CHahCHOCH.ClI,I) (CH. ltCO- - --+ (CH~)tCCH2 CH 2C H2CH :l2) 11,0I6. 64. CHaCHOllCH=CHCHs_6.65. 0. 107 c.OH- H.O6.66. 7 .64%.H, / KaT-+ ( CH3)2 CH CH~CH2C H2CH3(CHa)2C=CHCH2CH2CHaCH 3 CH 2 CHO1) (CH. ) ,Cl.\gCl ~ (CHal3CCHCH2CH:12) H,O IV. AJIb,llEr nJU"l H RETOBLI_7 . 1.p)CICH zCH 2CHOe)(CH ~ )2CFI CHCHOIOHHSr-+(CH 3laCC HBrCH zCH aMg ---+(3¢IlP)CHJ(CH3 )aCCHCH zCH 3 ~IJI)7.2.J\lgBrH,O -+s)r);11.)e)+ CH 0CH J CH COOCH a + 2CH;,Cl-I:MgICH aCH2CH211\gBr + OKHCb 9T1lJIenaCH 3 CH zMgCl + OC(CH 3 )2 • .uern.upaTa UIlIi(CH a)2CHMgBr + OKHCb 3Tl1.leB a _(CH3h CHMgBr(CH3)2CHCH2CHzMgBr1>1)Na6.53.
CaH,OCuH7-+7.11. }K)COH7 Na (CIllIliIl)190CtH~OCaH? -- CzHalrH.upu poDaHlle ·+ C3H70Na+ CsH,1 + c.,HaOH + CSH70HCH 3CHOHCHO. CH SCOCJ-l 20H.CHaCOCllO,CH 3 COCOOli •7. 12 .26.54. 06pa3yercli XJ10pIlJl AIiMeTIW OKconrUL B lKecTKIIX YC.1JOBHlllt MO}KeT nOOll30nTIIpa'3pblo CBll3 11 yme poA - KIlCJlOPOA (06pa30oaHue X.l0pllCToro MeTIIJla)6.55 . 6)CH3CH-CHCOCH~CH~CH :.CHsCOCOOH " lip.+ CH 0 • .ll.c fHilp aTaUlI lI+ CHaCH!.1COOCH l • .uerHIIPa-ra UIlIi.CH2=CHC H~M gBr + 0C(CH3)~' ,ll,erl1,n.paT3UIlIl.CHsCOCH,COCHR) MaJIOHOBbIli 8JIb.D.e rH,DJ 11 . ,,' . .Illl.ltJ10paueTOII; 1.3-AIIXJIOpnpOnsBoH.2; C;l OKCHM nponHoHoBoro aJ1 bJlerH.IlS;y 83UH UUKJ10neHTB Houa; U JlHldeT/lJlfJIIIOKCI1M; H llH3THJ1KeT8J1b UlIKJIOneJtTaHOHa; I .1-1U19TOKCI1UIiKJI OnellT3noH. -+ 2) Mg ( 9q.
lp) 2CH 3CH 2CH t MgBre)11)I) HBr-CHaCOCHO2·8.11b; 2(CH3hCHCH 2CH ~OHH)7.3. r) TpUMelHJ1YKcYCHbifl (nIfB8J1 HHOBblii) BJlbJl,entll. 2,2'AlrMeTHnnponaH8J1b;}K) ~ -MeTlL/IKpoTOHOBblii (llson POD nmtJl,eayKcycs bll') aJlb,n.ern.ll . 3- ..eTHJl6yreH. 2-Jl)nepBblACH 2 = CHCHO.D.) CH aCOCH=CH 2u)(CH ah CCHzCH 2CH3 6. 50 . npli ,Ilefll.npaTa UJIIl . C noc.'1e.llYIOll.\HM OKItCJleHlleM Xp O~IOBOH KIICJIOTOH,n.1I0Jl .ll.aeT Ce- AItKeToR. a DTOpOrl C.- D,llKHCJ10TY_6_51. a)+ CHaCH(OH)CH,CH.6.61. (CHB)!lCHCH(OH)CHa!:H~ CH3CH2CH 2CH 2 MgClr)-+ C,Hol6. 60.
CH aCHOHCH 2CH"CH J1)--,>.+ HI6. 56 . npoMbl.BaHUeM cepHoii KIlCJlO'roil (9 Jl,e.nllTeJlhHOA BOpoDKe).6. 69. PesKluHI C MeT3JI Jl UqeCK.IIM HSTpnf},l YK3sblBaeT H3 8MIUIOllhlil crurpT. Vis TJlexOfl TH'IecKll AellTeJlbH bIlI &l>IHJlOBbiX cnHpTo8 'I'OJIbKO oeIlTauo.rr·2 UpH OKUCJleIlHH&laeT KeTCH HOPM8JlhHOro CTpoellllll.oD)CI-I SCI-ICI-I 2CI-I Sr) (CHahCCHOHCH,CHs}K) CHaCHOHCH,CH(CHah7.13 . 8) naJlepllaHOBOii.7. 14. r) CH aCH t COCH,CH 3 • (Clls)2CHCOCH(CHs)II'7.
15. 11.) 0i8COCH~CH, CH'2COCH(CH.h7. 16 . 8) (CHsJ'tCA~l,CHO7.18. 8) K30npOnUJlH90BMHnSUeTllJIeH IlJllI 4HH300ynlJl3uernJlen.7. 20 .ECJ\ H SBllQane npOH3011JleT OTw,ennellHe rffApOKCIIJla aT c.~. TO ll BPllAY C 2. 3)I,IIMeTltJl'neuTSlI,HeHoM-1 3 (a TSKlKe 2. 3-AHMeTIiJrneHTa./lfieBOM- 1.4 II 2-nH.IIClyrBltHeHOM-I,3) MOryT 06pa3088TbCIi ~1IJI~mpem-ClYTfl.'1KeTOB H Menmompem8MKJ1KeTOH. ECJlII STlS'Is.1e OTm;ellITTCIi rI1APOKCHJI Of Ca. TO lfap"AY C TeNB}Ke yrJleeoAOpoA8MI! CJle.uyer O>Kll'ABn. 06paSOB3HII1I TOJIbKO Me'rllJl-mpemBMIlJ1KelOHa . TaM f(8K oOe rpynlW CH a • KOTopble MOryr MllrpnpoBSTI.. pasuoueHHbI .1917.22.{Hi.CHJCH~CHII(;HIOHa) CH"CH 2CH 1CHO _- H,O---.CH8CHeCH=CH~7 .5S._CHsGH,COCI-I;o~CH~CH:CH2Br~~__(1:1.0.,_CH9CH2~HeOH0_(H.O)7.29.7.31.7.32.>B) nepBbll1 cnoco6:fifio-CHaCIIIMgBr - - _~)CH~CH,CH20HCH sCH 2CH 2Br ___ CHaCHtCH\}MgBr _1'1.0CH 3CII,CH llCH zOHBTOpoii i.:ooc06:CH nCH 2 MgBr+ CH2-C H~_b'41-1 aCH 2 CH sOM gBr7.39.7.40.-4 11s CH'lCHPHe) R3 nponllonosopo 8JIbJ\erRAa .
a) CMeCb CHaCOOI-l , CH 3CH 2COOH n COt e) CMeCb CH~CH2CH2COOH , (CH 3 hCCOOH n CHsCHaCOOH ,OKIlCmlTMbHoe pacrueOJleHI1f> mpem·6YTliJl blloii rpynn hl naCT CO 2 ff OTQa CTHCH.'ICOOH.Ka p60KclI.1bHa.R rp yn na KRCJTOThI C HaHOOIIee AJIllHlloA QenblO ,ll,OJIlKH8 co,D.ep ·)K8Tb aTOM yrJle po1l8, KOTOP bl H IIXO.lU11 B COCTaB l(eTOrpynDbi. TaK KaK OKHCJ1I1TeJlbHa H Jl.eCTpYKU1UI MorJla n pOltOlll1'n. KaK DO OAR Y, T8K 8 no llPyrylOCTOpOay !lTOH Ka p60HlLITbHoJi rpynnhl TO 8 CMeCI1 J\OJllKlia 6b1Tb B K.1IC.~(}'T8CO,lleplKaruaR H3 OAHH 8TOM yrJl ep0Jl.8 MeHbwe. I,(XlTBeT'CTBeHHO, B HameNCJlYliae 91'0 1130sanepH8HOaal! H H30MaCJlS1lIaSl KIlCo/l OTbl .
OTCIOJ].a <pparMeHT Ke·STOHa6!!I~ --C';I:: II0)r)1927. 67,CH aCOCH 2CH 2CHO7.71.CH 3 CH 1CH(CI1 3 )CH(Oll)CH 3C1"i ~ CCI2CH ;;CHuCOCH;B.1. II)lJlB.2, e)a;)C H~CH(C I )CH(C I) COOH.CllaCH zCl I~CH~CH~CH(CH3)C H(CI-I 3 )COOHCHaCHcCH2COOCH2CH(CH3)2CH 3COOCH=CH 2+ C~H bONa+ HN(c.,II~)\:_llH3T11Jll\eTaJib aue'rolla;K)(CF aCO)20n)I1CONHCH3 (CHahCCO .,1)0(C HulaCCO n1lB8J11 11l01lall KHCJIOTa, r pHMeTHJlYKcycIl811 KHCJl0T8, 2, 2-11flfdeTtt Jln po£la ·nOBan KlICJlO1'8;iK ) Jl3()KanpO Hosali KIlCJIOTa, 4 ' MeTlIJlneIlTaHOBaSI KlICJlOTB, l· ..
elliJI~JIepHa·1I0ilaH KIlCJlOTa; M) ll30npOn I1JlcjlopMH8T; 11) 3T1tJleHrJIltKOJlbllHn 8J1bMHiar, c) N 3THJI<!JopMa~\II11; y) 6YTIlPOlll1TPIIJl, npOOlIJlIl1l8HlIA. mnpHJI M8CJIRIIOii KHCJIOTbI, <!J) 8MHAHII 1130MaCJI II Ho({ KlICJIOTbi .
B.6. r) YKcycHa H0 npO.llHOHOB8R, H30M8CJI SIlta II , Ji30BaJlepH8lio8an .8.S. LMecb KIICJlOT 06pa3)'eTc Sl Dpl' OKlICJlelllU! BTOPH'lllOI'O (HJlIl 'fpenl'lHOrO) CDllP'Ta 'lepe3 npuMelKYTo'lHoe OOpa30BaHIle KerOHa no cxellle:S.3 .Jl.)+ e m_ lCOm'lC/lCH(O H )C m \.. Cn_ 1COOH + CmCOOH ,71 -n COOHell<'1Ba1e.lbHO JVISl petlleHI1Sl 06paT!Ioii 38J!.8'l1t HBJl.O HsiiTll B o.!eCII KlIcnory C nail''1f:c.1oM yrnepo,D.ffbU aTOMOB. l1cKoMblil KeTOfl ,ll.OJIlKe!1 IIMeTb Ij>oPI4YJ1Y({CLoR' . T8KWd 06P83014, Ilhl6 paIl KIlCJJOTY IKOOH, MbI CBO)lHM 33Ad'ly K DOJl60pypa)lm a.13 R' . n.nn "lora nOACTaaJUIlOT nOOqepeAHO p8IlItKaJlhl KItCJIOT H8'iHH8R Cc a~toru BbiCUlero, IIMelo ruerocli 8 CMl!ClJ.a) AaH H} 10 CMea.
KHcnor (llSPIIAY c yrcJlblwil) MOryl JJ,IITb TPI! coeJlHUellllll:6oJibl1JHMCH:CH(CH 3h (pS3pbIB no JI IIHIIII «8~ 118eT H30BaJlepH811OBYIQ,a no JlIlH11fI c6. - 1f30MaCJIRHYI0 KflCJIOTY). Al18J10r1l1{]10 BropylO aapy KHCJlOTCOCT81Vl1l10T n ponnoHoaaSl II YI{cycHa H IWCJlOThI. G.!leAOBaTeJI bffO , KeTOH Hili eerCTpOeHlle CHIIC II ~COCl-J ~CH(CH ab .7.53.(CH3)lCHCH(OH)CH3H.OMg1) CH.O2)7 .66 ._(aq)llp )-B)8. O)J;HOOCHOBHbIE HAChIll{EIlIfbIE (lJPE):{EJThHbLE) KHCJIOTLIH nx llPOll3BOnHhlER3 8T1iX coe,n;nHe RHII, 1'8RKaK l'OJlbKO Oil 06pa3yeT YCTOWmB!iA npOAYKT npncoe)J.IiSeHILII C 8O)J.oA.
58'cym,<!JnTHaSl peaK UflSl 1l03BOJIlieT YCTal:loBHTb CJle,llyloIDIIi\ noplI.,llOKI 8lleTaJlb)J.e. rnA > aueTORAII3TUJlKeTOH. B) tITo6b1 lie 3aTpoHYTb ABOfmylo CBR3b J1 y'l~ IlCDOJlb9Oll81"b RSOnpOn8Jl3'r a.1llOMIIHHR (BocCTaHOI?JleElHe lTO Mee pBeiiHY - nOB.H1l0p<!Jy) , B) CH~ HeC(OH)(CH ~)COOH B JKeCTKIIX YCJrOBHRX MOlKeT npollsoilru 4e.
r l1.!lpa'iaUllll C 06p830BaHHeM :%, ~. )lIlMeTn.n.aKpIlJI0soft KIICJIOTbl. B) HCXOlllloe aerueCTBO - ltll3THJlKeTOH , I) CH.OICHlICOCH2CH~NHC,H6 H (CHaCOCH,CH,hNC,H.7 .62.CH3CH ~CHO7.N . 87 z.7.25. 0,509 .It3 •7.26. X.1opaJlb HBJUleTeS1 8aHOOJlee pe8KI\.ROHBDCnoc0(5XblN7.27.CHlC H ~CH~C H !COL..NH-oB) CH aCH...CH 2 _a, oHnepRllOff . T. e.H,O___ CH;lCHtCHOHCH" _(H+l-r)CHa CH3- CH-Cll,-C H~hH!CI-L-C -CHt- CH IICJ1 JCH.-CH2-~-CH,-CH~0116uB.9 . BJ CTea plfltOB8n KltCJI018 n rnltuepliU.Al eanepll.aHOnSI! KHCJIOTa 8 llMPdllaK (B 60JJee MJlfKHX yCJIOBHRX - aaJlCpaMlilIlH+_,D.lf91'ltJlHsonpO[l}{JlUlleHSMIIlIk , 227-8896) CH olCH 2Cl-t 1COCH,CH:CH s 11 CH,CH 2CH,CHO1938.23. Mon, 8f'C 60, CHsCOOH8.35 , 69% .
8,38. nOOOQHO o6pa3Y'OTCIJ nponllJleH II .l\Jlnpon llolloBblil 3!JJllp. 8.39. 6) CH 3CCi sC~H60Na - CH:,C(OC~ Hr,h ++CTpoell He KIICJlO11il yCTaa8BJUfll8eTCSI CJleJl,YIOu.-I{M•,CHa),CHCHCH,CHa - _=8.51. 665 e.8.52. (CH s),CHCO NH z8.62. (CH3)eCHCONl:I~ + Br2MaR a)+ 4J(OH-+ (CHS)2CHNH,(neperpynnnpoBKaTa lIaTpIH!.
BblTIDKKY nO.!lKIICJl I-lTb, n p09KCTparllpOB3Th 9(I)}fpO~l,cymHTb 11 OTOTJla Th paCTBOpIlTeJlb .8.69 . XJlOpHpOBaH He (B ITpHCYTCTBHH 1I011a) 8) l1aeT MOHOxnopn pOH3BO.!lHoe: 6) .!laeT .l\HXlIopnpOH3BOJlHoe; ,,) OCTlleTCll lJeliSMelllloA, Pa3JlB'laIOTCll TaKlKe CI<OpOCTbJO ~lTeplI¢HKaUHIlCHsC OOH8.76 .8.78.S.8S.8. 92.8.93.+ NH:;CI18CH i·..oNH~8 .95.9 • .JlBYXOcnOBHhlE HACblDl,EHBbrE (llPE.P;EJILHLIE) lU[GJIOTblD llX n:pOHSBO~bIECnH eCH,CH (COOHh)NH,x) disCH.CONHNH.,9.2 .
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