А.Н. Кост, Р.С. Сагитуллин, А.П. Терентьев - Упражнения и задачи по органической химии (1125895), страница 40
Текст из файла (страница 40)
B. A. Ka38!1CKOro C COTp. nOK838110, 'ITO npu K8TBnltnt ·'1CCKOM D.entApllpOO8ll1U1 napa(\nllloD C BbiCOKIlMIl 8LlX0ll.3MII oOpasylOTcll apo·16 .26MOTll4etKlle yrneBOJl.OpOllbi .1 - 9¢x1JeKT 8!lKIIJlhllbiX rpynnpOJl- yr.11epoJl. B )laJlhHeliweM\6.21. BHa/,6oHo 8b1ii '3lPu p .16.19. mpaHHCHJa) 811YTp llMOJIeltyJUlpK8R3aTeM BOCc-r3f10BJ)elllllO .C TepeoH30MepHble ,IlUOJlbl MO)/{1I0 nonY'IIITb pacKpblTHeM snOKllCl1 loOpa30a81Jlle- li30Mepa) li n !l npRMoH rII)lpa18llHell unKJIOr eKCeH8 DO BarHepy (npelfMYIUCCTBeIlHoe oOp 8'lOB8l1He I{UC-1I30Mepa 'Iepe3 M8)lIllO UIfl(JTlI'lecKliX ~lIpOB3.$ opMe B8HllhJ 8 TO aew.ecTBO 1I0J1)1(HO38Me.Cnl'l-eJ1ff ltOBOJJhUO 6nll3K" 0IlDOC r paHCTDe206tl~1e,er eHCeH - ,ceH- 'IIH'~3TO..Ha,e/l,e.!laTh 1<01l<!>0 P"lCpa.
e, rJJ,e16 .27.+cnocoocTByeTpa3pblBY cOCeJl.UeH CBllSII yrJle803MOlK1I1I. IlOlIe'lIlO . 1l30Meplls8uHII Depaoll8'laJlbilO oOpa3)T1OlUerocIl KeTOHa .a) WIKJIOnpOll811oaoe KOJIbUO 1I0npSIIKetlO HOTIIOCH"re..' lhHOneycToil'lllBo.ACHCTBITII GpOMa lJ,IIItJlonpona n oOpo3yeT I, 3-lIl16pOMOpon81l.16.28. G) Il-UJiMOJI.(1Pli2C1116.30.16.35 .8) OKTaHJlIlOH· 2._/"-~"--(- /-CH"t 7. APOMATlI'lECKUE Yl'JIEDOJl,OPOJl,hl H ax IlPOR3BOJl,llbIE,~PEAKnffiI 9JIEKTP00BJThBOrO SAMEm;ERB fl2». c6.H )l.eHTlIQIlhl Bee '1e1b1pe MO)lenn ea."c6.
I~ II dS. 5»: «6.17 .3.cO . 6,. cn. h II elL 2» .n _MeTUJlR30npODIIJl6eH 90J1 (n- UIIMon) ,17. 5. 6)r ) 1,3, 5. Tp HMeTllJl6eH30J1 (CWlM - Tp ItMeTHJlOeIl30J1 . llesHTHJleH,.G./- )CHS -_< A_~If"d J-!'"CH~-<)/ >0")I.~ 1, 2. 4 • 5_TeTpaMeTHn6eu30J1~o16 36.s)CH sIC1-13()11,0---+I I~HnC- C=CH,fl,O---+IH3C-C-CH,IOHa - TepnHHt."OJI16 . 87.16 38.16 . 89.OJ-!HaCI~o"/17 .6. 17. 7 .HaC-C-CH36HII~/UI~-9H3208(x~uCH'~ 1')34B) lt1IOPIlCTblil (\eH311J1It)l.eIi (OeH3aJ1bXJlOPH)I.):r ) 6e!i3OTPHXJlOPHJ1 ( 4Jel!HJl TPHlwopMeTall):)I.) 0 - 6p o~ITO.~ yOJl ; CH3C IJ2CH2CH2~CH3lK) n_ )l.lIXJ10pC)e1l30Jl .
H~ 2 . 4- AHilItTpOljlTOpOCH30J1 ; JI, q,cIlIlJllIllTpOMeTall (It' -mn pOTOJlYOJI)', p\ MeTHn oBbll\ 3cjmp II _ TOJIyo.~cYJlb¢oJ<HCJlOTbl; YCH3CHCH2CII 2CfI3tHs17.11.r)CII3 Cn,CRCH2CH3~~nep¢TOpIlHrpOC)eJl30Jl : )l;lIcjleHIIJlCYJlblj>OIl . ~,,- C\-l -~/ =_Cl -~_I'" __-CIe)~~~-SOP~ClaI..!!..»CHaT?,-/-CH:-CH,-<2-MeTJlJlneHTaH8 . PeaKIlHH npOTeKIlJeT no CJle,!{}'IOlI.lell17 . 10.~p) [ ,,/~V="1'~#- ~"OJs n)CHa-,,_67.5 2u)2CHaHIi r eKcaHa .()~(B p YTTO - cjJ0PMY./l8 e€ UlCCTB8 II ero npeepaU(eHlle 8 TOJl YOJl CBll.lleTe.'lhCTB}'lOT 0TOM.
'ITO 3T O t.leTHJlUH KJlOreKC8 JUten . OH cn oc06eH npHcoe,!tHlillTb MB..1efIHOBbiAaH ntltpllJl, 4TO Xap8J(TepHO ,!tJll! c onp m KeHHhl X JUteHOB . H3 H30MepHbIJ( Beu(CCTB TO.1bKO 5 -MeTHJlUHKJlOreI\Ca.u.Hen ~to}l(eT HMeTb OnTHlJectrylO aJ(TlIBIiOCTbcx eue:OJ,-CH- CH,- CHa I(~repn""~CH=CHII)A u eT8T Ooplle0Jl 3 rHJlp OJll!3YIOT II n OJlY4eHHblil OOpHeOJl OKHCJl RIOT 1!JI1f C noMOillb lO Ii H](e.~e80ro KaT8J1 lf3aTOpa ,!ter Hll p HpYIOT 8 K3M¢opy.i l ea KOJlhll816 .4 1.
12, 33)~/I,()l.YPOJl); M aJlJIliJl(\eH30J1; n) I - MeTHJlII8IjrraJlltn (a -MenlJlHacjrraJIHII); c) 1.2 . 3, 4-Te11>arl1J1pOnacjrraJlHll (ie-rpanIlH).lK) Me3BTIIJI; .1) Il _UUKJlOnp0D.llJlcjleHIIJI.,) CH'(~_CIl'~(mpem-neIlTHJI(5eH3OJ1): 2 _Menw - 3 - cjJeHHJI<5yT<lli)K----JI)~bsA~~O~N., C):)NO, NOt20917.14. 6) lllJl(JlOreKCHJl 6eH30Jl, JUlq,eHHJI .17.20. 6) 1,3 , 5 ' TP HMeTHJI -2 , 4, 6' TPH3TIj.1J (jeH30J1 .17.21. I<poTolloaall KOIi.lleHC allHII C noc.qeaYlOlqei1 apoManl3alllleil. BOJIee npena.pamCSH bMgX C n OCJle;l\YlolllHM I"IIJ1,POJlHSOM H apoAla TIIei!.O aeiicTaoa8Tb3allH BII17 .23.3HC==CH ..... 1II:III)JI)M)u)0)\8 .4.
a)6)C.H.r#)#)I I CH~=CH2 - _IAIC I,-j-~/I~ I6) 6pO\l HpOaaHHe , 3aMeHa6POMupoaaHHe .6poMB Hal(HaH,OMblJleHHe ADKIICJioTbl II CIlOB8lJ,py rue1i30Mepbl Aa'z{YT cpTaJleBYIO HJlU 1l3o<jlTa.17.44. 55 ,8 z.17.51. a) HUTpoaaHHe , 3areM XJI0P upoBaH ue;r) H A) XJl opHpoaaHHe , 3aTeM HIfTPoaaH»e;e) XJl opHpoaaHHe, 3aTeM IIwrpoBalifle. 06pa3YJoTClIO.I/IlTpo".1 0p 6eR30Jl IIn- HJUpoXJJop6eH30Jl. O pu .l\aJlbHeii w cM lillTpoBaHHIf O-HllTpoXJlop6eH30Jla no 1'1.53 .
Jl yqaCTC$l ! - XJI0p- 2 ,4-JUHlHTpo6eH30Jl n CMeCli C l- x.QoP - 2 ,6 '.I\HHH Tpo6eH30JlOM.f a npHHa)M e)K IIOCTb K apOMa TiftleCKOMY( n oco6HOCTb HllTpOBarbclI YK 33b1BaeT CPRAy . cOCTaB YKa3bl llaeT Ha rjl OPMY.ijY TOJlYOJla . 'ITO [JOATBeplKAaeTCII cn oco6 HOCTbJO OI\i!CJI fl TbCfI .1\0 6 ell30li ROii KI1CJIOTb/.17 . 55. 20 ~.17. 56.17.60.17.61.17.62.3) II 3aBHCflMOCTH OT YCJlOBllii ,,- flJlII ~-C}IJlbrpOKIiCJIOTa (o6paTIIMOCTb n pouee.ca CYJlbq,lIponaHJllI MOlKCT nplfficCTH K o6pa 30J3alilllo TepM OJ(UHaMIl qeCKlI GOJleeyCTOH ~IBOJi , XOTlI JI Me.llJleHHee o!5pa3YJOw.eilcll ~ - K I1CJlOTbl) .e)(npHRJlTO Ha3b1BaTb CT03HilXJIOPlIlU ) n OJly'caeTclI 113 TOJlyoJU.
Ii S02C1 2 'n -CH~C6HIS02CIB) lleiicTBlie PCI. Ha HarpHeaYlo CO,llb 6eH30JlcYJlb<jloKIICJlOTbJ (n OTJllI'IlIe OTKap6oHOBblX KIICJIOT c P Cl a peaKUIiR lie H.I\eT) .CYlIbcjJO XJl OpHpoaaclHe TOJlyona " Jl OPHCTblM CYJlbl/!YPHJlOM I npeapallleHHeBCYJlbcjJawl)t U o6pa6OTKa ff 36bITKOM xJl opa.18. Cl>EHO.lIW U APO&lATUlfECI<llE CllHPTJ»)OH18.1. Jl)O,N,,,,)/NO.I I"~/INO,21 0(M.U1tTPoQleUeTOJI).4 _MfTRJlpe3°PURU ;AIl¢eIlllJlOSblH 9I\Jllp (AH<\JeRHJ1 0KClI)t);~ .!»eHHJl9TilJlOSblli cmlpT;AMMeTIIJl<jleHHJlKap611110Jl;0 _oKCK6eIl3HlIOD blH cn upT (CaJIHfeHHlI);}J.B<jlemlJlKap6HHOJl «(')eH3f RAPM) .r llAPOJlH 3 lU\ Op(')eHSOJla;rn.eJlo'l1loii nn aB 6eH30Jlcy JlbtjJOKHCJlOThI;18 8 .
Il) CIIHo _B POMllHXJlOr eKC8H cp aBHIfTeJJbHO JlerKO OTlllenJllleT 6POMffCTblA nO)l.op OA .OpeHMYllle<:TBeHHO HlIeT aJIKJ,IJIHpOBaHHe B 1l8P8' IlOJlO)KeHHe C 06pa30aalll!eMnapa ·UHMoJla. 0 PH e:ro oKHC~leHiIllnoJl Y'lHTClIl epe<jlTaJlenallKHCJIOTaHOOCI--COOH.JleB ylO KHCot10TbI .OHIs) OKllCJleBUe KYMM a .17 . 31. r) npOn HJl6eH30J1, npOllHJll(HI(JlOrex ca H;e) TeTpan HH , AexaJlI!R (/fUC'H mpaHc-).17 . 36.-<-8) n-Kpe3OJli.II - 6pOM¢eHOJI ;9TUJlOBbilt 9\j>IIP .11, tUlTpo<jleHOJl3~(rr--CH,--CH,~iJ{~17 .
39.U ~3 I-IC=CH -~ CH2 =CH 2\8.2 .oj~C1-I-CH1-0HII)H.JPd#\17 .43.C1-I 8OHml ()?O~~/ISOaHC,I-hSOaN a -CeI-1ftS03H _<:.,H o01-l -OCHCeHae) CftHbOH CM C.B' _ CMeCb 0 - 11 n - NO~CeH40H pa3.1\eJleUlie 0 ...epoB oeperouKoi\ c aO.l\51HblM nap OM; BOCCTaHOBJleJiUe;+__NoOH+ NtCoH~SO,) - - .II- Nl-!tC6~S09Na + TI- N H 2C.H 50HnO C sH&OH (CN . ca»)llp yme11 n 'H 30 '/l .(H O )CeH ,N=NCsH,SOsNa -MeTOAbI: CbH&O H -> n.Hlnpo30<jleH O.'l . aOCCT8110BJ\emJe;C.H N0 -> Cel15NHOH -> /l.8 MIIHO<jleHOJI .26HwrpOB8HlIe ¢eROJJa (eM ce») Ii BoccraHOBJ\eHl1e nap8 -H30Mepa.2\8 .15. C H.+ OlITliAPU jI. IIHTapHOn KllCJJ011>[ (A1C13) -> CeH 6COCH:.CH COOH.
BOCCT a!:I0BJ\eHJIeAO C H&CH C1-I ! CH COOH, flllKJIll3aUHlI C 06pa 30BamleM a-TeTpa82zoJlOH a, )ler HApnpoBaH lle.'8.\ 7 . iJ{) caJJlIll.HJlOBa!l Kllc.TIOT8 fHaTplleBO!l CoJI.b)\8 .22. a) ajl.U0I1HOB851 KHc.TIOTa;6) 0 - 1\ n -HilTpOaHII30J1b1.18 .24 B) npli BBelleB1UJ ABylt II 60JJee HlIrporpy nn B apOMaTJ1I!ecKoe lIAPO CB!l3b aTOMa 6po~a C KOJIbUOM naCTOJlbKO OCJla(')eBaeT, qTO JlerKO liAeT saMena faJ10reBll:lIa fHApOKCJlJl .18 .26 .ca,1'')CH"QI ~OCH3(CH , ), CCI-->AlGI,~\~ /"OCHCH:IO~N"NNO~~~II I\C (CH:ih~AOCH\__.1C{CH:sb\8 .30. Kll c.TI01'apacTllOpl'leTCH B pacioope 61tKap60llaTa; !»eUOJI lIepaCTBopI1M 1.1 6HKap6oHa r e, HO pacTBOplleTclI II pacTBOpe rn.eJI0ql\; C.10iJ{!Il11n 9<jlnp HepaCTBOpJoIM 8BOJI,Il0ii UleJIOlJ.1I H8 XO.TIDAY ·\8 .3\. KaKy n .aMHHO<\>eB0JI8.
TaR II Y era AHalleT1!Jll.1I0fOnp01!3BO~1I0rOoplleHTllpyro·rn.ee BJ\1l!lflUe N_cOjl.epiKarn.eii rpynnbl ClIJlbHee, 'IeM B.'1I1I1HHer pynn bl . OAHaKO alleTIIJllfpOBaHlle B BOllllOM pacrnOpe 0PHBOjl.IlT K 06paaOBB'HHiO Tl _HOC H,NH COCHy KOTOPOro cao6olltllllR rliAPOKCIlJl KOHK)'pnpyer Il3epeaK1l.fUPt S8Mell.leHllllC 6o.nee c.TIa601'l aueTa~lIi1l0t1lynnol\. nO:nOMY 6pOMJfjlOHOIlH8BHlfe npHllO.I\lIT n peHwy rn.eCTBeHIIO K 2.0pOM-4-aueT8MIl o¢eY, KOTOpbIJ'QOCJle f HJij>OIlH33 npesparn.aerCII II 2_6pOM·4 -aMHlfo<jlenOJl.O-COAepiJ{all~el'2118.34.OH19.6.OHOHI YOCH.1:VOCHa~HOsS.1l)SOaB18.36.CH~O-<6H03S"()/OCII.QSO'H1>AOH(' Ii~ /"CN~/t 9 .8 . O) C eH u +C,1-I,COC\ 11J111 CoH, + CCI,I 9 _II _ 0) ECJlU BUa'l(!ne IlBeCTH rpynn)' CHO. saleM lCJlOPIlPOB8Tb , 'f0 S8Mem,elllienpeuMYlUCC-rneUIlO noflAe1 Ii MeTa . nOJIOlKelIUe. ECJlH >Ke cpasy nneC'Tll xnop.+ CH,O + H~ CH30--«-~-CH~ClCH~6CHaOH.1 ~H~)"OH--+~oN -OHII II(,O //~O"W.OI-l-....
H OWf[0flAPl1 C'TattOIlIlTCSI 3t-1a'lIlTeJlbIlOroIlcnOJIb90B3Tb XJlOPMeTltnl1poB31lHe " :> +ItboMeptioe Bew.ecrBo plI.l\oaoro CTPOeHl1 1f npaK11I l ieCKI1 He o6p a3yeTCH 113·3a CTeplJ<JeCKI1 X Q)8KTOPOB (BJlIHlIIlte coce.n.uHX MeroKCHJlbllbl X r pynn ).18.36. <DJJOpOrJlIOUHH npOH1JJl lleT cBolleTBa KaK ljJeHOJl a (apOMaTII'leCKOrO coe,ll,ll1Ielllllf) ,Ta l{ II KeTOl1a. n03TOMY JUr a30MeT31l .n.a eT n pocroii 9CPllP, a f1l.!1pOKCI1J1 aMIiI!_OKcnM (r ay-rOMepHaH tjxlpMa I1!np030c0e.n.KlleHIIH).~CH= CH-COOHOClIaU/',_---+ C l -<~NO;ON.()l-IOii llleJJO'l1>1O He pear lrp yeT. A!l.eTOYKCYCHbIJi 3rjll1P (ll el-IOJl bl-IOM cpopMe) .n.aeTQl,p aUlHl'atl He C FeC 1:;, 110 npaKlli l lecKII C BO.n.1I0H u.(eJlO'lbIO He pean-lp yeT _ <l>eHO.% 1 «B» H en B3aIlMo.n.e(ICTBYIOT C 06mlMH pea rE'IITaMII.r-- ..'18.41.