А.Н. Кост, Р.С. Сагитуллин, А.П. Терентьев - Упражнения и задачи по органической химии (1125895), страница 39
Текст из файла (страница 39)
Cf/(CHOH).tA 0H+ It + 3NaOH _(6HOH)t+ 2Nal + 2H,D&\lOH2'20113 .21.CO'°13.37. BoceMb.13.38. a)I'-H(CHOH),ICH 313 .22.HH=F" HHeao:to"HnHHCH}OHHL-"pHTP03"CHO~HH~onD- SplI l'\103a13.23. ~ R~HORL -T))l:oJaHat13 .46.HITH°HCH 20R~.D·ranaJCTosa2 . 3.6-Tp HMeTUn rJlJOK038 II 2.3.4.
6-TeTpSMeTRllTJlJOK033.KaK npu rII)l,po.nll3e 118I<.1'05"OHOooA KIiCilOTbl 06pssyeTclI rJl JOKOI10S311 KHCnOT3 , r JllOK03H Al1hrn rn)J;pOKCHJi AO,lllKeH HaxoARTbCli a OCT3TKe rJllOK03b1 . De)l,OaaTeJIbHO. n aKT033 n pe)l,CTaBJI 5leT co6oH ra.rrSKT03H,Ilo-rJllOKo3Y · CE 2 0H14. AMilllbl9n1tMeplf3alllU! aCllMMeTplf 4Horo aTOMB y rJlepo.lla. coce.z1l1ero C Kap.6oHlfJlbHOll rpynn oll ( 'lepe3 eH OJlhH }'1O CPOPMY).BpW (a) . (0) 11 (r) 5Jl.IJllllOrCli 90JlMepal.ut,C061!b1 K B3alfMHOMy npeapa UlelllHo.13.32. nD- rnnaKT03n13 .47.
TaJ<13.31. 4aCTlf Qna5J13.35.HCH 20H HCH2 0 HHvHD- TpeDaaH:!:H "+ OH )HCH20HCHOH--L--oH~OKHOH'HIKHOH." . I.n apbl (a) 11 ( B). 110 He (r) cn o.II) ClI~=CH -CH . - NH 2e)CH:lCHzCH1-NH-CH(CHs),II) NH ~CH2CJ\.!~Il~NJ-l~Ii)l(CHa),N}OHp) (CZH6 )~ -NOHOH°-r-Hn,..H!r)H)('''NIJzIl~HNH3 CElsx)~-r-HeRaH;l0H.L-3PIfT posa14 _2. . r )13 .36. OISere T p03b1 ,l{aIOT o,zam 11C n OTepeA aCHMMeTpHlJllOCTH TOT }f(e 03B30R. TaR RDR oOpa30nall1le ero CS5J 3alloy yrJJepO~Horo 8TOMa. oOyc.nOBJIIfBaJOUlero pa3 Jl1I QUE' MelK,lty 9TH/11K ,l{BYMlI reTpo3BMH:cnoyH- N- NHC;;HGH*OH- -f-NHc,H,HonC't.!OllHORC~20H~H0-=t=H.OR,IIC~OHD-"PIfTPDaa:?O2D·rjle03aMeT I1 J1~''HJ13MIlIl; 4 _aMlIDo - 2 - MeTl4Jlren Tall; N -!>IefllJlaueT 8M 1J.n .05a arO\13 830TS SClIMMe-rpHIUlbi • nM~Ol'Te-rp3aAplI'leCKoe CTpDelllle (Sp3.[,lI6pH)l,H3aJ.l.
Ilf1 u p6UTaJleil). n03TOMY c.~yqa A IIH a.~OrH'IeB BIlJJ"HOH KBcnOTelK)K)14.5.14.7.CROH+N~14 .9.s)IJMeerC5J .nBS sHTH n o)l.a H Me30(~O p Ma. npOJlyKT peaKlllU1 AIIMeTlIJIaMlJlIOMeralJOJi npn H36b1TKe aMlllISOOpaTHM O Jt8eT (/1I~_(,IlIIMerIlJl3MH\JO)MeTllft. OTUOCSluUtiiC5J K KJl3CCY TaK B33b1BaeMblX C3MHII3neb (S3OTHCTble aHM ont aueT3Jletl) .
8) npl~ aQC.CTaHOBJIeUlfll DOJIY'IaeTCSI 2 - 8MIII100YT311. B aneTOIiOBOM pacTBope06PSTIIMO 06pa3yelCS1 KeT8MliU, KOTOPblfl It 8OCCT3U811J111S3eTCII l18JlblDe JJ,O 2·8) nCpllHQHblitIison po n lin 8MIlH06yT8HS •llneper pynnllpoBKa frnpM8a8 OTlIOCJ1lCll K rpynne ceKCTeTllbiX oeperpynll 14.12. (5)POBOK asoTBcTblX coe,D;IIlIetmli. 06 PlUYIOW,11 Aell n pll AeiicrBll1l r aJIOfeliOS N - f3 nOre1l3MI1,ll, B w,enO'lliOil cpt'Ae re plier 1-11131 c nucileAYlome fl neperpymllfpoBKoA. O POMe>Kyro'ltlOe06pa90B81111e3¢Up3H30UllaHoaoiiIHlCJlOT bl 06b1'lAO lieyJl,3elCfI KOFlCT3TJI pOBBTb BmlAY ero Jlefl(l)ro rtJ)l,pomna203i 5. A1onIUOKllCJ10'tbl14 . 15. npOMeiK YTO'l HO 06pallYloUJ,llIicllnOTepu 11 pOTOHa If o(5pa30A3UIUIKa p6KaTII0l1 MOlKel' cTa6HJlU30B8TbCIi 311 ClleTMOJIeKYJlLI OJIe<\lu1l3 .t5 .
1. r)(CHshCHCHP-\COOHI14.28. 4 10 a.NHtCI-IsNH~ + CH sCOOH14 .30. a)2CH 3 NH 2--.+ CH ,COC I~ CH;JCONHCH s14.31. 0 6pa60TJ(oil CMeCH UJ,enO'lblO14.33. ~H.NH2+ 4H6 502C IIt3) 1I00CCH~CHsCHCOOHI+ CH"NH, • HCInOCJleAYlO u\t!1l neperoHKoa C BOAllll biM napoM.NdOH---- C sH aS0 2NIIC,ll.+ C6H.SO!!CI(C2 HI)~NH rNH.1CHKJcH~COON~OH+ HCI--+ C 61-I.S02N(C~H5 h+ HCI14 . 35. nC p'8H'IHO o6pa3YIomeecli N - lIInpo30coeAlmeHlle T3yroMepHo Kpaiille lleYCTofi ·'11l11<lM )' a.ijKIIJlJlH a3OCoellllHe.tIllIO . KOTopoe pacn aJl3eTcli c rtlTCpOJInTfl'leCKHMpa3p bl BoM CB1I311. o6pa3YSl MOJIelly.ny a30'ra. 11011 rUApoKclIJla It COOT l1el C1 BYIO'Ul ull K3HIOJf.
nOC.ijcJlfmil cnoco6en JlJI60 n\lllcOe.llltHIl'T L ItO H rllApOKclma. 06·pa3yll CTTll pT C lIell9MelffibiM CKeJleTOM. .llJf60 TCpMb npoT(JIj (06pa30B8J11leOJle<\luHa) . JlUOO Il00Meplf30aaTbc ll c nepeMemeHllelrt CI~Sl311 y r Jle poA-yrJlepo.ll, .nOCJl e.!ll UIR npouecc MOlKeT npUBeCTl-1 I( Kap6KanlOHY It3OCTpoeUH lI . CTpyKTypa/ · 3¢<t'eK'Ta Tpex a,lKllnb·KOToporo llecKOJIbKO 6o.,1Jee cTz 6111l1l30Balla 3a C'IeTflblX rpynll.Ta Koi'! KanlOn.
npnCOE'lllmSlll ru.nPOKCI1JI (06paTIlMo) . n peapa·maeTCll 6 rpeTlt411b1H cn llpT .NH~11)NII~CH2CHsCH~CH2CH2COOH T) CH:{-\-lCONIICl-lCOOH I16.2. II) <1. Me'fIlJl.(l· aMlIlIon pOITIIOIIOS31l KIICJlo,. a;)1) 6pO\ll l1AP8T 3'111J10(loro 3t\Jupa 2· aMKIl0t-.laCJIsmoi\ KIICJ\OThI . a) CH3CI-l ~NCl-IuCHJ1NO14. 38 .( Cl I3)~CHNH COCI .14 .42. r)(CH.hCIINHCONHCH(Cf-1 3 )206pa 3l:BaHIJ~1130HIlTpltJl a (0 npncYTcTBHIt 1I1eJIO'lH Jl)111 CBH3blBaitHII HC l):lK) paCK pblTlte 3nOKCH.II,HOrO KOJlbUa C o6pa30BBIllleM a ~II-I IIOCl1 l1 pTa.H<JiilUlTe B YQe61lJlKe npaw lJlo KpacyccKo ro ;3) Bmllllllle Ka p60llllJlbHOR r pynnhl lIa cOn plliKeJlHYlO AI}OHIfYIO COll3b yrne·pOA-y r .lepoA peSKO nOJlllpu3yeT n OC1lE'AIlI010.
Hau6o.nee 3JIeJnpocpun bll bl MB T3KHX CIiCTeMaX CJKa3b1BaerCll ~· yrn epoAH b11i aTOM BKHlfJl bBoii rpynnbl.no 9TOMY MeeTY It npOIiCX OllUT n pJj coe Alfll(~lllle a, OMa a30Ta alItHll3 .14 .46. a) o6pa6 0'TaliTe lIeOO,lbWJIM KOJlH'lecTBOM YKCYCHOI'O llHrHllpl1 JUl: 3cjJll Pliblii pacTl30p no.nY'le.tfBoil CMeCH n poMOlne HecKonbKO pa3 pa 36asJlellJIoii conllHoilKHCJlOTOIi AU nOJlIIOrO y.o.anelll1 l1 1'PI!9TH.~ aMHlla; KIICJlbl1 pac-mop lIeiiTpSJlH '3yii're UJ,eJlo'lblo.
9KCTparnpyi-i'fe 3cjlHPOM, O1TOHlrre 3(PH p . a 33'Te!-1 T PII9T11JlaMIIH ; 6) o6pa6oTaihe comwoll KIICJlOTOii II HIiTpIiTOM 113rpl1 S1 . no,~ yqeHIIYIO CMCCb pacToopHTe B 3\f'npe. y~a.1HTe 1pn3TIIJl aMHI'I 3KcTpaKUllefipa36a aJlemiOil C01l1l1l011 KlICJl OTOil, HsrpeflTe IleiiTpaJlhHYIO <jlpaKUIlIO C co·1l1lllOii" l1cJlOToil . 4T0(5b1 rJ l)lpOJl ll30aaTb ,llB3TI1JIHltlp03aMII1I. K I1C.1b1ApaCTaop npoMoirre 3¢lHpOM II IlblAenHTC AllaTHJI3MHH H3 KHCJlOrO pacruopaueliTpamlJauJlI! /i Ii 3K CT paK UIl eA 9<jm poM;B) 06paOOTafiTe 6eH3OJl CyJlb¢oX JI OpH~OM . OT.II,eJlllTe paCTBOpl1l>lI"n B meno..,CHnCH2NHS02CG l-I ~ 01' ue pacTBopnMoro Il U~en0 411 (CH :,CH ¥hNSOjCcH6 II(CH iICH~)~N.
tllApoJIIl3yfiTe pscrBOPHMoe 8 Ule.'IO'UI npoH31lO1l.Hoe.14 .47.CH s NliC 2 H.14.48.3·8MlI.HOneIlTall.14.50.CH 3CH aCHNHCH 3ICH 8 204_C HaN(NO)~H.(l_a~HmOnpf)nlIOH01l0iiI\IICJlOThl (aMIIA a - aJl3I1ulla), 1 KIICJlOTbl II 3aMCHOCt 600MB 118 alrtl\1l0 p y nnye) aMIIJl16.6.
Bpo,UI pOBa llllCM aw.lllaK8.lleilCTlllleM CH.I "15.7 . II)C zH.-C-CNINH ,+14.36 . a) CH sCH~OHICH~Nti,15.9. 6) (C~1-l6hN -CHCl-I~COaHICHa ~_aMIlIIOKJICJlOTbIfJOMilMOn 060QHO o(ipa3yeTCJ1 COJIb. a 38TeM aMIlA; A) llT8Ka Hen oJl,enCHHOH naphl 31IeKTpOHOB aMHII3 113 3J1e.t(TjlOIlOJlet\>IUlIITllbI(1 yrnc ·~-pOJ{1Ib1A aTOM I(Cl'Orpyn IIbl co CMI!II\CHReM ABOilROIl call311. B pe1lYnbTaTe o6pa3yeTCSIAIIMeTHJlaMlUlOKPOTOHOBblli ':It\lllp.
15.14 . '8) N- nponHolllinrJlllUliH.'16. AJUlU \Jlll'-lECltllE yf .!IEBOIl0PO )1.bl n liX llJ>On3BO)1.UbIEll116.\.e)CHsI£ H/ I ~·)CH-C-C~ \ CH.\CH~t2H& CHi MCtllJlllTIlM"U"KJlO1fIlOm'JlMI!T:lII\6.2..a.)~/H / -\-/ :---;"-',HCH~ICH3)CH3-H(~-C~H~t tu,~CHCHw)H2CHJ'cHs~s't~H.C.J:.H-CH~051:1)CHaCH jI0)tLi,.nR ~IIC-1I30Mepa a, a.KOHlPopMeP sHeprerlfqeCKB HeBbiTOACIi 113-38 npOCTpaHCTDeHHOroB38HMOAeficTBHIl rpynn CHJj.C)CHH. t ' \ H.,JH 2CCH tIIH.G"c('CHOH. '-../~-:j~~,CHICH 3-C= CH 2CHaHH21C::J-ca,11 2C/'cH2H3C-CH-CH~H16 .4 .e) mpaNc - 3 ,H4 • .n1f3TJlJIUIfIUlOneRTeH;e,lJs) I, 2-UIIKJlOncm'HJlSTlMeU;HK) 1·t.teTJJ.lI-4 - HSOn pODJlJIJJ.lJ.eHUIU<JJOf eKCe.H (re.pnIltJOJle.H).HaIll, G,p)CfI3o ()ICHa'-../()'-../I -NeTU.II1\ BKJIO.1"eKC""AUcll·l .
3CHaHIeR3~2 - W~1'II.II1\IJKJIO .r~C3,l1,Jle H- J.S5· ....T I~n~lJKno.I'eKcn,l\Heu-J . 3(JO.IteT aCH ....eypU'lecKllllyr nepoi\ll)HCI1 3'-../0CHaI/~l)a-MeTlln4I1Kno_ 1-lIeTun!4U!<JJQ .1'e.KC:1.1llfeH - I •~/'eI(C8.1(1l""-1.4CH.CH2""3-W8TllneH_4 'NeTHJJefl !4HKno.0 0lUllCJlOr CH-16.9.fa-\HCit,):lJUI mpaHC·HSOMepa B l}lopMe xpecJla 8 01MO)l(IIbI $a KOHc!>opMepa; e .
t-KOHtj>opt.tep npel\nO<lTUTeru,llee., Ta K KaK 3aMeCl'JlTeJIII l:laXO.!l HTCIl J1an bwe J1p yr OTa,a16.18HJlPyra .e,l:BKOTOPblilKOI!)lCBcaUIUI KJlan3<'!ua J\aeT lUtKJlOneH TaJiQfI - 2 - Kap !Ia)lOnO)lBepmyn. KeTOImOMY pac luen nell!llO . a16.22.MaprallUeaoii KIICJIOTbI)06paTiITe BlIlIMalillC 118 003MO)l(IIOCTb paCWllpClIlI1l II CY)I(ellUIl UltKJla .pa60T8X 3K8j1 .