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- [CoCHjOySO^, [Co(H20)JCl3, [Al(H20)JCl3; 6a(W36(8)3ab 3nc;>33'3c:j3ao6) -
[Cu(NH3)JS04, [Zn(NH3)JCl2, [Co(NH3)JCl3; 3;g^3^6 aGoo-
63ao6) - KjjBeFJ, K^[Fe(CN)J, Na3[Co(N02)J; 3ocoAp)Jbn3c»)35c;>3jb3ab (c:>oa66co3ao Jcnofoco^ojmob 3^*3-
^3^06) - K3[Al(OH)J,K2[Sn(OH)J,Na2[Zn(OH)J.
3036 bggrtnb 3^b|8>nb dnbgi^gno) .>(^83336: — [Cu(NH3)JS0^, [Ag(NH3)2]Cl,
[Co(H20)JCl3; iGonS-ain - Na2[Zn(CN)J, K^pFeCCNy, K3[Co(N02)J jo^ G3o5(^ic:?'3<o - [Pt(NH3)2Cl2],
[Ni(CO)J, [Cr(C,H,)2] 3"3^C-0^>a!^l>.
663<<}(no)d a^rtggoticjn jcn^dbnbdigSn Soj^uongGgaob dnbgcggnofi .if^BgggG: 3co33co3^-2(Si Gojiggab - H2[SiFJ,
H[AuCIJ, H[BrF^]; g-adggib - [Ag(NH3)2]OH, [Cu(NH3)2(OH2)2](OH)2, [Co(en)3](OH)3 co6
3co33jio35b'36 3^(^ocn3aij - Na2[Zn(0H)J, K3[Fe(CN)J, [Cr(H20)JCl3.
(33G^Co.iC;»*g6o 6^(»>3ob (groG^cjjg^^^eoGoG^SGgcnob) Gocooogii gcoSicog^b-geoo G^gfoooob \iih^^m{:o^6So
bfoga^ CJoaiGcogiob '933j:o33. iGooG-gf^o cjoa^Giogaob bi^bgj^jiynjogaib gciggcjwgob ^jgb "o"- co,ia(»)g]0{»>3a,i.
3iia'iC?oo>iico: jcjnfoo (Cl~), ocofioro (I~), 3oj:D<^(»)jbco(OH~), qo^Gco (ON"), Go^tno^o (N02~), g^acoGiij^ro
(COj^") coo> .!».3. G30(8)<^,>c;>'3(^ C:joa.iGc03ab ijgb Gogooogfogiob •gogcjgsjljo Gn3363C:j.>5"3<o'3jrno b6bgc:;i^cnc»3a.>
(coo6'bn(5 - N2, gcnocjgG - C2H^ po^ 6.3), Isroaogfoojo a'i3coG63e;>obob6 (6^36 - H2O, 63oG - NH3,
g^eoinGocj - CG.Go^'^t^'bocjj - NOpoi 6.3.). 365ocoG'3(<io ^o3c°oa
Go^eocncno-gSo - N02^,Go^foto'boc:jcy23o —NO"^,Joj:!o6co — £06 6.3. c:;joa6Gj:ogaob 863r>o)3cj6 bio3a6 6Ga6G'3(^o
a)663o3cD33iwaoa).
Cooa6G£03aob (^inQbgob 6c:>b6Go3G636so oggGgbgG igiodG-gco ^foggojbgab: 3oGoco3G^6(8)'3foo C!>oa66co3aob
333o>'b33363o —jjoo- , , ^3(8)<^6- {©6 6.3., b(*)c;>n bo- j©.i ^j;[noco3G^6g)'3(©o c©oa6Gco3aob 333a)b33363o —
iob- ,^(oob-, ^3(5)<^«>3t>b-,33G^63ob- j;d6 6.3. 636bo)6G,3b ^^^g^ojbgbo c©oa6Gco3aob 6Ga6G'3(oo o)663o3cD336naoo)
jo6b6b3c;)3aob6b 3b3co33c©(*)a63o 6<o 3oo£;>3a6.
33^6pcoob ^Gggob b6(^ob'bo 6t:;>oGo363a6 eoco36'2c©o Qo^t^oo), i^co33c©o0 g68l5oc©3a3o, 33^6c©ob
^aSjoga. 636b(n6G, 6Go{*)G'3(o 3c»)33p:;>3^3a3o 33(8)6ci>b 6b6b3c©3a36 c©6o)oG'geoo ^^dS\i^<^cxQ(^Qomy
b-ggojbo "•33"-ob "65"-oo) 33(33ci>ob 36(8)Om6'3<o 3t*)3^c:;>3jb3a3o 30 — 3«^(^a)*3c:;jo
^(^6Gb3<ooo3Qooa>, 33b6a63ob6co, b6b3c;>(»)ao(» £06 G6o)3b6'gA a<o'2G363o.
^agScoo) 3n336Gof[©o6 "bnaog^^ooo anG-icog^-g^o G63(^a)ob «g(»)fo3'3c©6 £06 b6'b3c:o'^(*)co3a.>.
K,[Fe(CN)J a6c©o"23ob 33jb6(306Gco<g3(©6^o(II)
Na2[Co(SCN)J G6(5)<oo'ju3ob (^3(8)(#)ia)onQ06G6^(*iat»)a6jin^6^o(II)
[Cr(en)3]Cl3 ^<oob3a)oco36£oo63o6j(©r)3(lll)-ob jj;:©coioo£oo
[Co(NH3),Cl2]Cl (8^3^(^663oG£oo^£:©n(nnaDa6p::;>{8)(IlI)-ob jQ[©ro(no£oo
[Co(NH3)3(H20)](N03)3 - 33G^663o66jg6ac»>a6c:;>(^(in)-ob Go^<©6^o
[Pt{NH,)A] JDO63oGfi0ojj*©C*)(^t*)3c©6(8^oG6(n)
[Cd(enUCN)J aob3(noco3Gcoo63o6£ooQ06G(*>a6£o3o'33o(II)

24
 3(^636c:;»gj}(^D363iol! ^m-^mo ao'bg'bo 8^0 o'bnSQfoQio'b s^\i^fKn^66. .>8 S6if>cn^'Bo
o'br)836ooli 8(»)3c:)36i a.rffioe^oiQi'gcjo^: 6) c^joa^BtoQiob a^61jlS3633i'3c:oo 6c;>6.>3t»)ioa)6 poA jonf^oG^Qooo); i)
^036 3Of*)t^)ioo6i0O'3cno Lg3(^)(»>lj aiGljb3i335«gc:jo JipijeA^naoo); 3) Gi^oco^jQiob 3.i61>li3i33&'3c;>o 36G6^o(«>gioo)
3(*)83cngj\>'3(^ o'b{»>836ool> 8cX<ioo>6coo "bilSQQicw: ljcoc;>3.i5'2(tf)o
(^opoi^j^^-gcoo), 0006-3(^0,33n83^f^o'3c:jo po6 (o3(8)03'g(^o.
Cno3^pogi(n^6 po63633o(ogaoo) 3(»)83cjg^Gi3<nor)ga^o 33li3PD3ai S3ob (3.>Gol)6'bc;>3<ogaA 3(^0)0 po,i 08^33
jrno36GjPo'b 3«i6'b'b3.i3gi'gc:?o 3c»>co<^pooG60ooa>) po6 bAjgo)<«)03 c?oa^®'C?'*^ o^mSgt^ogio. i8o'b o'b<n8ge^oob
3(*)i6Ci>^(III)-ob Go^i^n- poti Go^(^(*>'b(*)3(*>83cn3jb3&o: ICj[Co(N02)g] po«i K2[Co(ONO)g]. 8ao)^
C^o36Gjoob (NOj") 3(n(n(^pooG60(W bne^jQogcopoQi^ 6%co(8)ob 6G ^G3a.ipoob A5n83^K3li b^^-gAcng^Kxx). 6G6cnf*>a«'3^'^»
(wooQoiGi^-ocoGo (SCN") 3n83j«)gJb^6<f>8<»)8^63c:»b ^godcjgi^ po6'g3A33o<oio3b 6%co(8)ob (otooqo^G^^co-N-
3(o83cng^o) 3D30<^poob (o>cKnQO,s66(8)(»)-S-3Co8ico3^o) ^^dGoo). 3r)n(opooG6QO'gcno o*bn8g6o6 33lS3Pooi.i
G^gf^cngi^o, (^)e78c;>oioQ 3gpo3gi^ Jf^SaEjjg^-geoo ^GocoGobi poA 3(»>83c::»gjb"g<no 365oD6ob636G, <on8gcno)i Bn^ob
Cno3^pogiob 36G6lpopj;)giA 3«^b363gi'gc;;)o,i:
[Co(NH3)J[Cr(CN)J [Cr(NH3)J[Co(CN)J
fntn-gc^jo 3gpo3gGoc>maob p[no36Gpogio,8i36cnoo>6po,.i8o6n8g63gio,o)3oa)coG 33b3jwgij> bfeg^i^bbgi obooGgfogiob
biboo), <o(n8gc^OT.i 3nco6pooG.i0O6 3r)83c:ogJb9^8n8J8Ggcno>^G o^gggb g<^>ooG6ofoo 3gpo3gGoc::)oaob^ jo^
3^b363gi'gc>o (wgobgig&ob 3co33ff;>g^66g(^«wgiob (big-gcnfoog cjo3^ioob obn8geoo6).
btncjgA^^jrto (3oi5<«>d^^e?o) o%n8o(«»od 3^3o<^)cobgi'gc:jo6 3^bbGgc:job 8cocjg3'gps:»giob 3^6bb363gi'35ioo
3J»Gi^ocngaoa> 3(o83cngJb«gf#)o G^gfoOTob 8036 poi 36(03 b«gg(^(ogib 3(o(oob. 3opo(o6(8)-gcoo o'bco8g(ooob gco^bog-gfoo
86362^00)06 j(o(o8(III)-ob Jc:j(o(^>opoob o*bro8g(^)«gps:)0 Jopo66(8)gao: oob«gg(^)o ^ggg^ocncoiob 3gJb66^6j(oD8(III)-
ob - [Cr(H20)JCl3,8fO0obg(^{o-8^36Gg 3g«gg(ooco(oaob igG(8)66536^to(ocoj(o<o8(III)-ob jc;>{oe#>opoob
8toGto3ojo66(8)0 - [Cr(H20)5Cl]Cl2*H20 P06 8'3jjo 8^3683 33^3(^>020(o&ob (8)35(^>66j36poojc:;»(o(0(oj(oco8(ni)-ob
^P[j>co6opoob pOo3opo(06^0 —[Cr(H20)4Cl2]Cl •2H2O.
ob(o3g(«io6 '3363'3o(^)po3a6 po68^b(8)-gcoo c:oo36Gpo3aob 36Gbb3633b'gc;> ^c>B6^o^^6'\i gcoa^pjjgjb-gfoo
G63(oo)ob 8036 jDA 36(^)3 bggt^fogib 3co<oob. 86362000)6*0, 53(8)(tf)668oGpoo^2?f^<^d"^C?6(^'^)""^ Go5<o6(8)ob
- [Co(NH3)4Cl2]N03 o(oG'g(oo 0^(083(006 (8)3^(o668oGGo(8)(o65coj2:;j(»'<^f^3Cob620(8)(III)-ob -
[Co(NH3)4C1N03]C1. ocoG'g(^o obco83(ooob 86362000)06,63(^30)33,(8)3(8)(^668o6pooj2:?"<^"'^c::j«i6'^(^)""^ b(oco8oj;oo
- [Pt(NH3)^Cl2]Br2 po6 (8)3^6668oGj:ooi(^)(o3co3206(8)oG(IV)-ob j2:a"<^opoo - [Pt(NH3)4Br2]Cl2.
ao«^9o6<^«t)C?" obio3g<<)06 368(o^33'g2::»o6 jroa^cogjb-gtoo G636o)ob 8036 b«g3(o(ogo 2?oa'^0^^
36Gbb36g3ig2oo •g(^)or)03(^o>36G20633ioo). 68 obnagt^oob 6'gQ0203i32oo 30(0(0^66 8036 3(O(o6pooG60O'g2:? b^ggt^Ko'Bo
6(06863203^ (o(oo 36Gbb3633i'g2?o 2:?t>a'^C?"^ 6(ob3acob6, 686bo)6G,6b30)o 2:?o36Gpo3aob (ooQbgob b(opo6bo)6G 3(oo)6po
obco83(^)3aob (o6copo3G(oi60 865'g2o<oib. 33ro8g(8)(oo'g2:;jo 0^(083(006, do(ooo)6po6io, 8gjo63Gpo3a6 (oj(8)6gpo(^'g2:?o,
56(8)33200 3g6*o66(8)ob6 po6 336pD66(^'gjroo 5o668opoob 6poG63(o5ob aijcoGg 3(o852og^b'g6 663(00)35^0. ^338(00)
8(0336802006 pooJopo6(o^b(03(o5620(8)(III)-o(oGob (b-g^. 3.2)
Qob-^66Gb 0*5(0836350.
H,N

b^6. 3,1. J5063o6poojjcoro6(o3c?^(§>o6(ll)-ob Qnb-^666b 0*5(0336350

b6oG(8)363b(o6,6(o8 pooj20(o6(oj5o68oG3206(8)oG(II)-ob 62080^6-3200 0*500836350 360)86830)056368 36855363*0356
666 866^(0 <30*503-360 *o6 ;jo8o-g6o <0305353500), 66683*0 50*020(030-360 6^(8)03(0500)6(3. (305-0*5*08365 366B806
86(0206*0 368*056^-3200 boSbogGob 56^0866*08*033*0 *030535350, (^6685- 0*5*08365 30 —666.
NH.

NH. H-,N NH.

OH HoN bg6.3.2,
fi>g^>6668oGi5n3o*56(ojjbf03io56i»o*S(lll)-o(oGob
OH Qob-jgjrtiBb obcoSgrtgbo
25
 n'bmSgrtod *br)gog(^<j)0 ^coS^cngjli-gfoo B^gfncnob ^^bg&co&cogb
biS^iiBISDSoEiingio^G bogC^QQ^o ^jgOTiigbgi^joo, n^o g^oco8.i6gcr)ob b6(^g'3c:oo g68nb.ife'2C^J33ob b.ibocr). o'boo8gfnoob
gb biibg agbgcogAi obgo) jfoS^cog^JbgiBo, <nr)3gc:ocD,iQ .i(n ^jgcn bo8g(8)(^oob boiin^gg. JggSfocn (b^fo. 3.3)
giScnb-ib-gcnOiJ M(A,B>C,D) (8)0 3ob 3f^93c^gjbgiob D^^og-gtoo o'bm0g<^g2>o.

B , B

b-grt. 3.3. r>3^nj"3rtn M(A,BjC,D) (^o3ob

(8)g(8)rt6giofn'3c? gn33cjajjb9n

3.3. dOBO'otnO aaoaob &\D6oao 6^0fn0)0a30

giiC^gB^-gfoo iSgiob Sgmncoo ogn jg^ib^-geo-Sgj^Bog-gAo ajgnf^ogioj^^iG ^ofiggc^o, f^c^Sgc^oQ a>i9(^yg6g3'gc;^

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^»i^o^c^^6nblib 3Bo9g6gc;;>cog^5 ^^ncJlb obA-gcngib cofo6cofn'gc;>-.i(jQg3^n(^'gc;no •gCncnog^icogSgiDgi.i C?ng.i6cogib6
(fonSnfogio) £o»i gr)83cogjb^.i<o8cn3j86gc;nb (^^g3^co(^n) *9n(nob, .icnGo'SB'gcoo Sgj.iGo'bSocr) gng'iC^gb^'gCno i8giob
^6(o8nj86ocn liobbSgio. c;^og.:>6j:ogiob 3g.>Q(n.iC° g'^Sbi'bcog^'gcoo bngf^Qocoo giiGcn^ggiii
oCnggc^og is8 i3giob d^'JC^'bg 8.>c^^.iCoo 8^og^^.i£;Q(^&i coob(n(joiQoob6co8o.
'3^Cn'^ ^cjoGo'SGcnb, <oco3 cot^6c^^o•gc:o-.i^g3(^n('^•gc:no -gt^cnogfocojSgj^giji bnC^Qogjioj^gi.i jiCni
gro83cog|jb^.>63n8j3Ggc:nob go>fog gc:^g(j^(^f^6-gc:«o 9(oob (nj>gob'g<g<ic:no S-, p-{W6 d-cn(nio^.iCngiob 'b>i62^'bg,6<'io>8g£D
0^0^306^(3'9C?'^ (^cnc^oigoibo Joi^ojo-gp^o c»)(^(!>o(^.iCogiob 'biif^j^'bgjfnoScogioQ gojBb^i'bi^gfo'gc^o 8o8o>Acn*gc:;)gioa)6.>
ooe^og6(^o6gi-gc^o bogt^Qg^o. 8<igj)c;noa).!>£o, Cll^^ onGob 3d-jggcon6ob nfnio(8).3C^gi'bg (3,icf) ^oo<oob
gfocno a>^'g^ggo!^;igigc;»o) gc::jgj(^(^n6o.i, bcocoD agnmbg oGgf^2,g(8)og-gc;oo pocnGob S-, obg p-^^jgj^coGob
rof^io^o>c;;5gio coojgob-goj.icooci. congosGpogicn^G (3.igOpc:>ocno>pw, ,i8oigob Sooc^gg-gC^ogimtiG) •gf^cnogtncojSgpogiobtib 4s-,
4p^-, 4py- 4p^-nt^io(^iC;|igio g.i6oQCoob Sp^-doifoopooliiiQOib po.i Sopngi-gcno Joic^opo-gp^n n£^in^t>c;;>gio
(^(^og6(^oinpogi.i (8)g^<^«^gc°t^ob ^ggiocogiob 3o9.i(^cn*gC2^gio(7) (b-gf'i. 3.4).

yz ZX

b'grt. 3.4.Cu^'^-nnBob gcrgjJ{8»^nroB'gc2jo joi bogl^^OOTO ^cjBi^roSA

.i8oo>gob 9{^c;jgg'gc;j'i'9o ^i^bn^ob .!.(^co9ob 3'ic^gb(^'g<^o cot^bo^.>C^>gio, ^3(^gf"gg, sp^-Job6opo(>'b.i(^oob

8pogc^3.i(^gr>iii'9oi!> ncnbo r)fnio^iip:^opo66 g^ocy)-g(ncn*bg 8coa)6gbgi'gp[;;iOi> o^gob'gtg^ppon QCjgj^^f^b'gc;;;)o
^3302:00. o.8o6gob cocobo Smcjigg'gpiljiob oi'b(»)(^ob L!>(^n8giob cocnbo sp^-^obfnopo-gp^o cr).igob'g^,32;oo
^3305^0^00) giipoiooj^f^giii Cu^^ocoGob cnLigob"g<g.iC;?o Sp^-Joi^oto-gppno c^65o^.ippagioa),.ipo6o9G'g{:j)0
bcig^mco bj^gi^i pOtV 8g.sApogi.i cooobo N- Cu^"^ bS^ (b-gCn. 3.5).
 h\n^'

3.5. N- aSg&ob 66(f)8fn^d66 [Cu(NH3)^I^^ jro83c?od^t)'** o"63o

[Cu(NH3)J^'^ J"9^SC?0d^'3<^ ck*)63o Cu^^-ckoBo 63o6^ob 3coc:;>aj-3c::»j)&o>.i6 iBgib .b3«^6j)ili Sp^-3oi(^>oco-2jn)o

ro(tf)6o(8)6c«oioof). 3e)bj»c:;>c»)so63c?o ogco, <oro3, 33a>^6ob 3coj«»aa'3Cjob 6Gic:;»roao-a(^).ijo, a"93c:»3jb3o c^jo^-iBcogao
6o6'^W^"3C?" 3o3A<oor)'3c:;)3ioo>. Cu^'^-oroB^o ^bginiob
cjo^^Bj^aiob 5o(8)<oo3toe^)-3c;>o a«^c?^ao^i 5<#>.iBb^n63o<ocoai6 ifo(8)aoc? 33'^'^'^6"3c?'^ ^•^)-
NH,

H3
ML.
[Cu(NH3)J 2+
b^(«). 3.6. jmoaABcogaob &(<><Jagc?o J3iCo<^A6X3C?o a^GcjAaga^
•3^6r) a«^3^O0C?3^'3C?"^ ^6 6"^"^ 3"93co3jb3io. ^bQOD aciBicngJUgib ^^(^BnjSBob (6aoBob,ac«>i.icj5ob
'boaoafoOTo hh^6 3a(8)^cjob onBa^o. 36a-isc?oo)oij^3ob aaagodcjoi BnaoagiBcoo) [CoCNH,)^''" an33c:iad^*3(^)o
ooBo. Co^'^-oDBob 3d-j3ajo(»)6ob n65o56c;)ab*ba ajgbo (36o> 3co(6ob 4 aK?ad6<^f^^"'^»
3ar>a)ba aBat^aa^og-gcjo conBob S- C06 p-jaacofoBob co£6bo(8)6cnabo a).i30b'3<gic?0'i. i9oJ>3a)6B •3foo)oat6of)j3acoa^b.ib
Co^^-oroBo ->c>a*'^6ai'3c? BtogcoBit^ani^ao. ^3 co(6cob d-jaaj^nBob a'^a^83"c?o^oc?" oc?od6<^"^a^"
^t)3oc>{oab^, n6o d-co<6bo(8)^c!o cD63ob"3<gcnj3»0^'> 1?-^ d^sp^-Jobtnojoo'b^Qo^. ^^(nSD^BBoc^o ad3^"30
3oi(6ojo-3c:>o o(#>io5^crjo o<6ojjB(8)0<6aa'3C:»o^ (»>j(8)^3iDi6ob ^aa^^f^O^obiga^. b^n<6aco ^3 n<6bo(8)6cna^o<" 0d3^"
conBtnfn-acoo ^3o6aob 3coj^)a3'3C?^ ^6<63cooJ3Ba<i<^ a<*>93c;jad^'3^^ gti^onBo (b-gt^. 3.7).

H3N

lCo(NH3)gl MU

b*g(^. 3.7. cjf>a^GlSO^''^

coJ(8)i3J5(^)-aCoo a(»)B<goa'3f66Qcw ^Si>?>So6 fogoBob^ joi obacn 3ro(#)030(^oB-3c:)

27
 3.4. jn83C?0db0a0b dO^b^-^O^bB^'OfnO
3n8onb65'bo

6.i3<oa)olj 8fiDa(^)ifi0«iolj a661j6'bE03<i>ol>^3ol» 3.i63ol5oc:jcoo> ^3 jcoS^gjliol^

M + nL ML„ n

[ML.]
^•" [MHLL
B^oo 3ol>o 36o^3G3c?coi6, 3oor> S^jn^cncKS S^c^6\i^co6'^ 6^<^)333o j(»>93cjgJb'g(^o G^Qfowolj
3o5QQ6(8)<#i^Q(W, ^<3 3oo) •a^gfor) Sjoa^itDo^ a^'boc^'gcjo ^coS^cugJlo. 6^310^ 3^co3cooG6(^)3, ^3 Ijofoojogb
j(n83(mg;jbob dcogf^^i^tn&nb gmGbig^^bfg^db
OT-g 3D33cng^^A(o3n^36ob fog6^oob 363O3(^).i£0 3663oboc:j>630) 3o33c:j3jb6i3(^o)ob cDobnQO-iQoob 3<^K^0gbb,
3iM ^gbtii^Sobo 3^3og6b bo»bgcn^ncog36 ojGgii a"93c:i>3^ob •a3cD3f^^(»)5ob gnGb^^G^^.

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060666-3500 (p=const) 360(3363606 5060b a6<g66o)036ob 8-386066 W= -pAV (5.2.), 66506(3 AV -
606(8)3806 8o03joo6ob 03500503666. -36630^000 Go36Go 80-3000)366 08663,608 60503660 606(8)386 8-386066
5663 86503606 9^'^jN^oa 9o6o 80665660 3^3^a^ 800650366.
ff>^ 56(366003606 3-3860606 60 8608363500666 B6363680 (5.1.) 566(8)05036680 50.i 6636(8)66360 866(^03
566506^6366,803050360:
Q =AE +pAV =(Ej +pV^) - (E, +pV,) (5.3.), 665060 Q^ 060666-3500 66003606 600606,06503^360
1 2 30 3680666636,836666806650, 66003606 669306 506 66605000 8503086630666. 605005036 (E +pV),
60835000 966806503366 606(8)3806 8^3086630606 g-3650O66,6C2^"^"^3O^ ^ 66000 5o.i •39<*'C03J!>3B 3606506066
663 60060838033500666 (63686. "en" —80 , "thalpos —60060):
H = E + pV (5.4.)
60o6 3603650069063600 (5.3.) 366(^050366 663 B60936366:
Qp=H2-H = AH (5.5.)
6860365V, 060610806 8553086630606 ^-36(10066, 6085006 0350050366 o6oa66'35o 36o0gb3o 606^3806
8036 8o?g5'3(oo 600606 ^05006.
6556660866306, 6o8 6360680360 60653806 3606506006 666050-35-360 8608363500606 3666665:23^'^
83-38503635006,606 36800 0368050066803-36 368003503680 03363636 3606506006 035?o5O3666 (AH),608350660
65030500 6^6 60653806 3600 8503086630605066 8306380 3650663500666.
0-3 60653806 850308663066 00350366 8-3508030 800-3500606 606063680 (060^06-3500 6600360), 66-3
AV = 0, (5.2.) 36650503605066 803050360,608 36«g66oo36o6 8-386066 W= 0 506 036805006680306 60633500
3660606 3680866633500 (5.1.) 3665co5s:?0^-^ -^1*0 B60936366:
Q^=AE (5.6.)
3.0.80663660 3636306 85sa<*»8^<*»0"^"^ 9"^" 03C?"C?oi^ 060806:350 66003680 6o6,8>38o6
8036 8o?36:35]oo 600606 (8)05006.
60653806 360650.^06 38653660-360 ^666835606 506 60300363606 660503606663,
53863665-36666 506 9633663. 680508, 3606506006 036?o5O3666 66365066636 66003606 50606 6665:23^'^33®
656650^65-350 606063680 (60300363606 6605036066 - 1 80500; 9B336 - 101325 66; 50^'^0^'^68^'^ ~
K). 66360050,656650665-gjo 606063680 a-i'6to8o5o 333506 0368050066803-36 <3-3680066 65060866336 8366668060
6086050000,608350660 63506 0650386650 3936366 0.86365000650,63680006 656650665-350 8050-36 3606506066
36806666336 AH°^-oo,8o6o 3666080503666 32^/80500.

37
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ijjogocio ijg'b 'bol»(8>g8o'b g(^a»o 8co3n8ii(^>g(*)ioj:o66 8g(*)<^g3o ^ijo^'bgcjjolji'b.
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3^^8030 SGggob 8^198030 8m(3ge?n8ob 3n(«tn&3&8n 8n8£^A6d(«i3 l^gddong&nb 360)^(^306 oB-j) boo)8;3(«)o
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'bg8<»)0) Sogg^Bocjo b5g8ob 80)53(0300), bob(8)g8ob Iw^gobo 8(03co86(ogco8o(o66 b^incooxo 8io3P)86(og(»)868o
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AH,
bi^golio <^36336(8)330 AH, <^36^000!) 3(<)r)(5-gj(^3io
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B AH4

1) g(oo)b(8)6(oo66o 36(*)0gboo), (n(*)8coob g6o)6codo66 AH^.

2) (»)(o1j(8)6ioo66o ^(^roQgboo), ^"g^cjjgcio'j'jt^o A 8(030)86^300606 3632:000), <00082006 (362n3g'3(::oo 6^6(003606
350)652^303606, ^366668066(0, AHj (06 AHj-
3) 6686^6(oo6Go 6(000(33600), ^6203(o'3(^o B (o6 C 8(030086(^30063606 3632000), (oooBgnob (362:u33'3CUo
6^6(003606 360)6520603606,3366668066(0, AHj, AH^ (06 AHj.
63606 36600606 o)666686(o:
AH - AH, + AH^ = AH3 + AH^ + AHj (5.7)
0>3<o8ooJo3o63o COO(DO 36800336366 6^6 6(^6 *3^652000(0 63606 3660066, 6668350 806366 368008(006663
^3(0^366. 606335200 ^3(03306 or)666l586(:o,636^(3oo6 36006520606 636^0006 66oo(o"3^^36o6 ^66800^606 3600620603606
5^68066 (06 66^3060 636336^3606 ^66800^8606 36006520603606 65203366*35200 5^6806 663600606 (8)0052006.
60660066, *36(06 3630003652006^060000,6008 600*35200 603000363606 ^66800^8606 6(8)66(066^*35200 360O6520606 866^030
60300036363605066 6(8)665066^*3520 60600636^0 1 8005200 60 603000363606 Ip668ooj36o6 636^0006 360065206006 (^0052006,
60052000 866(^030 60300036363606 ^^66800^8606 6^665066^*35200 3600652060360 6*352006 ^00520650 6606 80663*35200.
J3606 36600606 *6380065060^6*35200 ^350330 66365066636 603000363606 ^66800^8606 36006520603606 ^680033636000
866365200 636^006 (0600 '800606 063000 6000^080*360 636^003606,60083520006 86(8)66366 in vitro ^g'38{ic!jo^oc?o>!»)
3G006520603606 56666*6503606 66'3*365203666 08520336. 8656520000650,56800300365200000 36666805006 606003*606 636^006
36006520606,6008352000 0065660*68^0 6806305066 506 666^06665006 50000^0500(066 600600352050366:
2NH3(6) + CO3 (6) = (83) + H,0 (6)
AH*>p=[AH*>((NH,),CO(83)) + AH*'(Hp(6))] - [2AH*'(NH3 (6)) + AH*»(CO, (6))] =
= [(—333 —242) —(— 2 • 46 —394)J 32c/*3co52oo = —89 33^/8005200, 6650^0 -333 32^/8005200, -242 32&/8<*>52oo,
-46 32s/3ro52;>o 506 -394 32s/9r'>C|?f>, ^36666806650,36666805006, ^352006,68063066 506 666^06665006 50000^05006
^66800^8606 6(8)665066^*35200 36006520603606.
63606 36600605066 56800850066630066 83C063 ^31:03500, 600852006 0066668650, 6065066060 636^0006
36006520606 350606 ^3^336500 636^0006 3600652^6066 ^366*^36*25200 60B6000.

5.3.0)0(o8nc?n6^80J0b 800(^0 306n60

00368005006680306 606335200 36600GO 68366366 66005036006603 00666*3665000666 606^3806 ^066566 3G365066,

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8068650600, 6oo8 333(2o«i ^080*260 636^006 600600352050366 86005200050 08 ^380063336^0, 600503660 606^386
3665636 36365066,66*2 66000360 356oooo3632c:oo6. 68368650 06006052006 866365200 365doooo368*252;jo *30*603*260
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47
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do(^)oo).ii3®o 3i68.ilil53633b3C!jo Go^.i6o^.
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0C!J0dd)^"3CI?^ (3000-3500®C):
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^36co56(:o0>66:
6Li + ^ 2Li3N + 2C (CN)^
3Mg + Nj -> Mg3N2 3Si + 2N2 -> SijN^
6*5(0^0 ^ 'g(6o)03(6o)j83j:o351) 3(030(6100)66 jo6 36co{033635o>66.
(nbg3^coo ^%(«)5o (i'bn^o o)'bg3.HO(og&6 -196°C-'bg) goBobi (oi c?c«)<#i^t«)3.)6o j6<61jo1j co<)i36co{)igioli (333^a^aio,bicjgio,3,)3ocjn93io)
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4NH3 + 30, -> 2N, + 6H,0 4NH, + 50^-> 4N0 + 6H,0
(0650366 6806305 8(05033-250630 65(0(^5 6^5 -28006350 2j'5633o5 566o55o (-3),2j»56336-6c;)50336o(n 636^0035^0
NHj 6350365 85C050C050 650850336 0030535355:
3CuO + 2NH3 -> 3Cu + N2 + 3H2O 2NH3 + 3CI2 ^ Nj + 6HC1
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48
 o>goTjo&oio. a-j^GaAggiOTiG -afoOTogCGOTdagcogioljilj NO ^gcngGlj ^jo3coao6 (ngoligigili. aig^cjooDijo,
o^^a3iA,l5r)C>r) (^)gAaoeGgio\iAl> ^s(hdcoiSSo\i 6o5fon*boc:>fcn<ooj:ol>:
2N0 + 0\ 2NO2 2N0 + Clj ^ 2N0C1
agnogfo .ic>ajoag6gio>66 6g6ao(^>3iob6l> i*br)5ob afoGnjbofioo igcjgGb a-j^gig (ngobg&gib:
2N0+ 2H2-)'N2 +2H2O
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Go^t^o^gib ^6(^a(»>j36ob:
N2O3 +H^O -> 2HNO2 N2O3 +2NaOH -> 2NaN02 +H^O
(o6jog6G.iQ Go^fno^gi'ao .i%n(8)b ^jgb ^itCjgfio'a^" t)^830^ b.it^)obbo (+3),a60f) "agodcogii g^aco.igcno6nG
(ncognt^Q ^Gjogj^o, obg a^6Gg.igo ogobgigio.
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NO3- + 2H^ + 2e NO3- + Hfi
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HHb(Fe^O + NOj- + 2H^ ^ ao<nHHb(Fe^O + NO + H^O
HHb + NO ^ HHbNO
aQOT^ganacj^^^Bb iw>> Bo(8)<^'bco33anacj'^^Bb {j^Babi^^^
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(Gjjoa^ aaojJoacnac^cnboG^o JobDjboob a^an agodcjabA nAa^Bobago a'><^o>-3c;ab3bo a^o^gonb.
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"S'SO^'*' boo)bob (NjO^) ^6^Bco^dSocn'.
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g>i£?<i^gXJC?f>^ 9i(^3£gGog, 140®C-*bg go —a^t^QbGog.
i'br>5(IV)-ob njbofioo ac;>og(^o G^-iGgigo^. Gib^o Gt^ig^cjo Gogo)og<og86 o^gob:
2NO2 + 2C ->N2 + 2CO2 NO2 + SO2 -> SO3 + NO
g^bbGob^b NOj ^^Gn^aGob ^bro^G^g^b.^ ^bn^cog^GG^igib, bncon ^-g^gg^^
•gfoOTogfnwJGgcogiobtib —Go^ioi^gibib j:o6 Go(8)(^o^gib:
2NO2 + HjO -> HNO3 +HNO2 2NO2 + 2K0H KNO3 +KNOj + H^O
ib(^5(V)-ob ojbocoo •3<gg<oco, g6ajgoi^)giC:;ja gfoob^icn-^eoo GogoDogiogi^^. ogo fo-i ooo^bob
(8)ga3g<^6(8)'3eo.ibg(3 go ^jogoco^co o^cijgii ^^GgftijiDob g^Gngn^oo):
2N2O5 -» 4NO2 + Oj
.>3ob g^an ac:nog<oo a^.!kGg.igo.i fioA Gt^^g^cno cofngiG-gcjo Gigt^ooo GiboD^G ^gbgiob^b .i.!»c>s:ooi->' 9gA<o
35ogro3,i<^gr>8c>'Go ogo Go^(on6o'3Gob Go^(^6^ob (NO^^NOj") biboo) ^6bg8nbb.
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N2O5 + H^O -> 2HNO3 NjOj + 2NaOH ^ 2NaN03 +H^O
ibco^ogiGG^igi b'gb(»)0, iioiGcogeo^joo Gg^g^i, f^JOjGgcooo ^fobginib Ggnogf^ S-^Bb^ggi-acj bb66<^>g8^o $56
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ai^bgcirgioWlj
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joi 6c:>-3ao6o>iG, fo^iog^G G^o) bgco63o<^)bg ^^t^jGojGGob Qog groGQgG^^of^ga-aco Gg^gi^o -gbbGico ojboj«-3<#)
^bgb. 63o5c«>G gcoG(3gG(8)(^)o(^g&'gc:jo ^bco^Gg^g^b g^joi^^Gi ^godj^jgi^ ^G Gg^^cogiobig^ so^ab^gi-acjo
9g56c:>gio)^G f#>g6gof^>g8ob6b 6bD(8)G-jigi ^cjcoggii bbg^jo^bbgi 3f#)coco^^5gb6Gcog h'Bo(h6fo ibo(8)ob
GtoGr)- to6 (oonjbojo^g). ^ifoGco^Gocj d(^)coco-3^(a>a)i 3gEoggGocjnb.b fo^Grogocogi-acooi Gg^^c^job i-gGgiibg,
49
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80IS3C0300), 6{:ojD3g6ol5 3(^50*3^(8)0 3308203^6 o^nliNO^ ,N0, NjO, N2j:!06 NH3.
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S + 6HNO3 (30)60) -> HjSO^ + 6NO2 + 2H2O
3P+ 5HN03(366'b) + 2Up -> SHjPO, + 5N0
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0301)^060 oo63ol)*3g65o 85030866303690 ^668o^6o1) 6681036083 6500(8)6030*350 l)6lS3l)l536o36l)i 003006,
^000350 J06 963 <gol)<go61). 0030060 ^ol)go6o 0305001)8633660 603000363366,608500!) 36ol)(8)650'36o 831)360
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03060 ^o3go6o3 3^3663 660336 ^080*360 36363003 3o6605oo3 363630650 366506^8663 *336390610336.
go3<go6o ^080*36650 850036 6j5o'36o 666335«i52jo<i' 650056080*3500 3o5oo<go360o33o3 ^0*360 6j5"3f^^'^
860936350036650 3663336350336 36086630036366. 86365000650, 03060 <go3<go6o 8636*33 665050336 60°C-*33,
^003500 - 270°C-*b3,30500 9630 3636005? 0B363 66503303 *36663. 333SI?«> ^0^or)^303*^^'' «go3^o6o3
^3o363 80050336 <go3<go6(V)-o3 oJ3o5oo (^663365003 6635033o3o363 66 63500 ^330363 <go3<go6(in)-o3
0^0500 ^66800^86336):
4P + 5O2 -> 2P2O5 4P + 3O2 -> 2P2O3
363*36330363 go3<go6o 83565033066 636306333 ^o3<go5033o3,30500 666835«HS?0^«'>'^6 —go3go6(III)-
o36 50.^ «go3«go6(V)-o3 663603303 ^6680^600:
3Ca + 2P-^Ca3P2 AI + P-^AIP 2P + SClj ^ 2PCI3
2P + SClj -> 2PCI5 2P + 3Br2 -> 2PBr3 2P + 3S P2S3
<go3«go6(ni)-o3 0^30500 0og ^365090 o336336 ^o3<go6og66836363 ^6680j36oo, 30500 03350 ^365090
8085006663033 5oo386o8o60oo3 ^66336-65050336000 636^006;
P2O3 + 3H2O ^ 2H3PO3 2P2O3 + 6H2O PH3 + 3H3PO,
<303^0603668^636 *3^360, ^365090 36636503366500 83660 60300363366. 030 06^*380660 836366.
^663oj86o3 369*36500 («go3<go533o: Na2HP03, CaHPOj io<i ^^3-) c?*^ ^^36 (8oco6o<go3<go53io: NaHjPOj,
Ca(H2P03)2 106 333.) 866050333.
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60835000 ^3650066 50*3500500363 66 6o.)303633o363 o6oogo3<go6836366D (363,633"3sc?0^"3' ?3t*>3o3o6836363
*3^0503336) 3661060^86336. 33 *33^663363500 80050336, 6363033, P2O5-03 500500 66050360300 03350 ^36co9o
3633600:
P2O5 + H2O -)• 2HPO3 HPO3 + H2O H3PO, P2O5 + 3Kp -> 2H3PO,
go3<go68g636 03060 36o35'>6so*36o ^365090 36636503366500 60300363366. 030 368^*380660 836366 50
^668oj36o3 368o ^o3o3 866050333: <go3<g6(^333,8o5o6ogo3^6^3336 50.) 500805060^03^6^333,
PO^^ 0063303 66080363606 Ag^ 006330:
Ag^ + PO,'--^ Ag,PO,i
(go3g6(8)-oo6o3 33666^3 336035003 6o^66^o3 80^83503300 368030^0500 5006 33003500 66503J0 —
AgjPO^, 603060 3336IJ6 o5n3<g6^o, 8500360 836363 sD686^g3o363 0336336.
<go3<go68g6363 200°C ^388366^*3663503 3603350330363 ^668oo(]36336 8o6o<go3^o68^636
(6oogo3<go68^636):
2H3P0,^ H,Pp, + Hfi
33 8^636 oo3<g'38o66o6, 863668 ^663o^o3 86605006 06 6033 - 066666035033*3503 50.^
0036666035033*2503.
Rn8Bbn1>, *33S<^3lo*3CJo 3g8irf>A6g6olj6 C9.> 6-3^1030533^306011 l>(5)<'>"g56"3'^'3C? 30360636^3611
^.><^3c-)»(og361i. 33CJ01J 811030^^0 do(oo<n.){o.ico ~ ^^10(^^4)6(^^)2^ .Xwli ia36'jjioo, '33C<^3CS*3C?o 8386^6360 —
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6oc»>o<g<»)lngo(8>36oli 860^631:^103^60 ^*36800^ (0^3^601)990 3i53o3a<^3o61i 363(^130011 .)3*33*3coo<^o6ili6 co.) 3a'^''>3'^a'3C?"C?'>6
36ioo3rt3*j)lo (^13^8003^^ 3oli 3.)Go.)^6.)9o.

60
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3Fe + 2O2 FCjO, 2Mg + 2MgO 4A1 + 30^ ^ 2AI2O3
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51
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36!S'3(o3^!)6b •33^o)(0346 333c:j6 03(8)6cnb 330)oco^4o(«)-3(^)o 03(8)6j»o34o!) (00j(^)(o, 4co6(8)o66 (o6 !)b3.) 36(^6 (06
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Fe -I- S FeS 2A1 + 3S -> AljS, Hg S HgS
S+SFj-^SF, C + 2S-^CS2 S+Clj^SCIj
33(o0!i(5oo!)^365:;;)o 3(^0)6(03(^0)0 03^6c:];)O6, (^00035000 30030(^(00)66 (^3630(^)34!) ooo)6lJo!) ^3043(o6^-3(^6*b30. 60
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S + 2H2SO, ^ 3SO2 + 2H2O S + 6HNO3 HjSO, + 6NO2 + 2H2O
3S + 6K0H -» KjSO, + 2K2S + 3Hfi
36050(536(^0 3oo3o(^^ ^36co46(oo!) 36^6(^3400) 005034-3500 30030(^(0^365546(004 b!)66(o!) 03636 (^36^0^6
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2SO2 + O2 ^ 2SO3
SOj 60350636344 (^00300(^0 "1*0 9tl-^a'^3 «h:?9(5336o4 (00055^0
33335506346:
SO2 + Br2+ 2H20->2HBr + HjSO, 2H2S +SO2 -> 38 + 2H2O
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53
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NaN02+ 2KMnO, + 2NaOH -> NaN03 + K2MnO, + Na2MnO, + Hp
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54
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2. bgb^o Q'gdg jod 3obo jd^otnGo. 9i>g.3c;>oa>6co, i'3<30^'3C!?f> bob^gSi — NHj/NH^"*"—
•^dot^jobi) (»<> ^ScoGo-gSob jjjjcofnocoob bb6»i(^3o (9oi^33co3iob pH 8,2-10,2);
3. 3^63^(OA bAB-jjicnjm SdJ'iocjo iGcn^oo $^^3^ ^GonGgfto. 9A^Ac;>oa>Ai:o, 3Afobn6A(^'3c;;>o
bob(8)39A —COj^'/HCOj" —6A^<oo"g9ob jjA(^in6A^obA (oa Jo(o<o(*)3A(oi(o6A(9)ob bb6A<n3o (9(»>^3j:og6o'b A<ogAc;oo
pH 9,3-11,3); gcobgA^-gt^o <^'3'go^"3C;jf> bob^39A — HP0^^"/H2P0^~ — 6A(8)(^o'29ob Joj^t^ngobgA^obA
(OA (ooJofio^nojob^gA^ob bbGAfoBo (9fnj9g(ogbob a^^qajjoo pH 6,2-8,2). 9a^o(;oo)A gb bob^g9gio ^godc;»giA
9o3Ag'2a)3Br)(n i'3«g3<^'3C!?<> bob^g9giob ^ot^gggo ^o3b, 9AgAcooa>A(o, gcobigA^-gfo bob(8)g9A^o
H2PO4- b-gb^o 9gA3AA.
4. A3Q(nc!no^3&nb nnGgbn aG 3r>(»o3j-gc^gio. 9A(n 9ogg*gtngGgiA A9oGr)9gAg'g<oo (oa QOcongAGo b'gggtG'gci^o
bob(8)g8gio. o*brog{rogj^fo"gc;) ^gfo^ogo^o (A9o6fo9^A3Aa)A 9rocog3'g{|nrjgio, do<noo>A(oA(o, o9gfo«ggiA io ^njioAfo-gcoo
onGgiob bAboo)) AdoGnd^ggbobA (oa Qojjijgiob bbGA(ngio a6aa b*g<gg6*gc!J"- <"'3 Abg<n bbGA^b (OAgdA^giA
GgAgAb aG ^•g(5)ob gAt^ggg^gcoo foAco(og6cobA, a9 ^gdoobgggA^o Qogogbob GA^ogoo gAjoAfioob "(3ocoA-9gAgA"-b a6
o3co(^9a3o (OA ^A(^9cooj8GgbA b*g<gg(o'gcoo bob^gdgbo: a) b-gb^o "QojioA-dgAgA" joa a9 dgAgAb
9a(oocoo; i) bgb^o "Qoj^oA-^-gdg" joa a9 ^"gdob dAfoogoo.
R-CHCNH3)C00 - + H» R-CHCNH,)COOH
R-CHCNH,)COO- + OH- R-CH(NHj)COO- + HjO
bA(OA(3 R 0OC;>ob dAg(0(*)d(*)(logg-g(»oob Ga^odoa.
dgAg'g^^)0 (^o3ob,dAgAcoo(nA(o,A0g(8)A^'gfoo b'g<gg<^"3C:;jo bob^gdobAcngob bbGAfoSoH"^ ocoGgiob gco6(3g6(^foAQoob
gAdooDgcoA ^godc^gbA ddAiodgAgAb (oobooQOAQOob gAGjSjcoj^ogbojoAG:
CH3COOH ^ CH3COO- + (9.6)
_ [Hn[CH3C00-]
[CH3COOH]

rxT., T. [CH3COOH]
a8 gAG(8)(ocogbo(DAG In J —1\ [01.13000"] ^
b-gcggfo-gj'oo bob(^gdob dgnfog gndbnGj^^ob, GA^foo'gdob <>(33(5)"^^^^ oAGAcobobAb, (ocndgoob (oobroQOAQoob
btocoQgbo ^g-gjoggAjooA, (9.6) gAG^nj^ijgboa) gAdcobAb"gc;jo ^(oGAb^nfG(obA g^^oGAQg{s;>gib dAfoQbGog. AjgjoAG
gA9rod(ooGA(og, ddAtodgAgAb AfoAcoobcoQot^gb-gCoo dcocijgg'gc^gbob g<^bQgG^<oA0OA bJ^A^^og'gcoAjo Ad d^AgAb
gnGQgG^foAQOob (8)(*)cooa, bfopioco AQg^A^-onGgbob gnGQgG(8)(oAQOA —dAfoogoob jroG^gG^foAQOob. ^gbAbAdobAjo,
(9.7) gA6(^ncogbA Abgo) bAbgb doo(ogbb:

[H*] = K (9.8)
®[dAf^ocoo]

(9.8) gAb^ncogbob gAc;o(ogA<noo)dgboa) (da -l~*bg gAdtoAgj^ogboo) doojogbA 3gG(og(*ibmG-3Abg(jjbAbob

gAG^mcogftAl

pH = pK
• [3a^3'^]
bngAjoAjo g3gC!J«> ^o3ob b*ggg(o*g(i2;jo bob^gdgbobAogob JgGjog(obcoG-3AbgcobAbob gAG(^(»)jiogbA Abg
fiAo^gfogbAl

„ .^1 Pa'3g;g;oi^-3g;"
• [33^3'»]
dAgAdjooOTAjo, ojrobgA(8)'g(oo b-gojgfoobAoogob Ad gAG^cojjogbAb Abga>o bAbg A^gb:

pH= pK(H,PO,-) +

JgGjiogt^jbcoG-jAbgj^nbAbob gAG^njjogbob (OAbdAfogbooo BgodgogbA gAdnOTgfiooc;;) o^Ab:

73
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^•g^ob $o69.>^35obi>b •3b.i*b$o36o .>6 .i6ob. ^9 •36660b 66o$!036o56o3o $D6b6bo6o>35ob6a)3ob ^390^6602006
^•3gO<^"3E?o (8)336coo5ob 06356.
dcong6o 8^6g6b 66 033«3^C?0^&0^"'' 66oco36o56b, 60832000 ^6(io6 GD6386Sob 1 e? 5'353o6g2o
bb666b 8obopH-ob 36010 g6o)g:3co'>oi 3o^^G3C?OC?^t?> &^)g3<*»X3C?'> 5)03^C?'^i^ 36020356.
603'^^^'^ 93636b 66 (8)'3(8)ob 9ob3$o3oo> (90200/20) 366ob6*b$o36356 939C0330 «go69'32035oor):

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c(l/z^) 9363ob6 $56 ^'3^ob 3330362036^35ob 9020*360 306036^6600350, bo2oo IApHl - (^"g^ob 66
93636b jo696^35oo 3<i9o^33'32oo pH-ob 03$!5OC5O^(>1^ 8o$o"32oo.
93b6569ob6$o bb666ob 5'3<g36*32oo ^33«>$oo56 ob6$o356 9obo 3o95o636^35ob
306036^6600606 9o96^35ob6b. 696bo66633, 336£036bo6-36b32o56bob 366^o2035ob o666b96$o, 6o$o3b60 pH
= pK^ <g66$oo56 [^3'3$5$is;j35*3joo ^*383] : [93636]=1. 306036^6600606 6833660 O6660366$oo5ob6b bb666ob
pH •3«g6o 66320356(0 00320356, 30(:d63 bb36 839ob333358o, $o6, 6^31066 369o9$oo6663, 5*3g36"32oo (8)336$oo56
96jbo9620"36o6 5*30336'32oo bob^39ob 30850636^06 o666566o 3o6036^660O35ob6b $56 69 860836320050(066
36(06b66bo66 360620 90o6$o356.
5*3g36'32oo bob^3935ob 9oJ93$o35ob 83^660*580 3663obo2ooo 603^6^*360 5*3^3605 86362000*53,6o92oob
9oj93$o35ob b6o}*39332ob ^66806(03365 o3'393-9^63'36o ^o66b^o6o56:
CH3COOH CH3COO- +
603^6(8)-Oo6o6 9o6o06(00 ^36606 8200360 3203^^60200^0,66^60*3805 603^6^01
CUfOONa CH3COO- + Na^
8200360 9^365 (o696^35ob6b 83*3(02035*3200 <3*383 50^635 00635b (06 5*35(8) 83636(0 366(060^86356:
CH3COO- + ^ CH3COOH
603^6^-006350b 3o6036^660oob 838006356 *5*35^6(0 308536506(0356 886683636b 8o2033*3206a>6
3o6036(8)660oob 36*56(000,60b 83(0336(060 6(006086356 80063 03C?"C50^'^ ^363056 (06 8obo 8660200b
306036^6600606 o666g66(Do568o (06,83b6568ob6(o, pH *38608363200(0 00320356.
^*3^ob (o686^35ob6b 886683630b 560^06350 368oo63ob*3<g2;o(0356 (06 6630(8)6620355 (0686^35*3200
(8)*3(8)ob 006355,366(o6(j85ob 66 860 ^ycoob 802033*320356(0:
CH3COOH + OH- ^ CH3COO- + H2O
68 838053336800 b(0356 80063 8363056 $306 8obo 8660200b 306036^6600606
o666^66(oo568o, 83b6568ob6(o pH *38608363200(0 O032og56. 886683636b 306036(8)660005 03Cooc;?O^*^ *5*3b^6(o
308536506(0356 603(^6^-oo635ob 3o6036(8)660oob ^6*56(000.
666200^0*3606 5536 5'3<g36*32oo bob(8)3835ob 80^83(03505 83^6605800. 86^620006(0,00200366 5*3^36*320
bob(^3868o 8200360 83636b (O686^35ob6b 560(8)06350 o5o^356 0O2oob 86602003660 ^06800. 68 (o6ob
38*^3*^1* 660(036056 *38608363200(0 056(0356, bo2oo 86602003660 go686 3330362036^*366(0 8006(0356,
68o(8)o8 pH 866(]^03*32O6(o 8*3(08030 66356.
(8)*3^ob (O686(8)35ob6b "00206-836365" 568*36203500 b(0356 OH" 006350b 8350^36. 68 (o6ob 00200b
86602003660 <30686 *38608363200(0 056(0356, bo2oo "00206-836365" 660(036056 3330362036^*366(0 8006(0356,
680^08pH 566(]^o3*3206(d 66 00320356.

74
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8"2jo9o3P)iob 336i><^B"3GgiA — ^•383-8363^60 3p)83nb^6%o. 6c^8o66ob n6366n%8b 366^606 pH-ob6 {o6 ioncjngou^ boo)li33i'3o
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08336(00 6633408 8^630660408 8'3£o8o3o4o8 336668^63468 '3C®oco38o 8803363(50046 6J38,66(0366,5^36 3600 H'*' 006340 86636(500
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668306836368 ^668058600,6083(5100 (5080006(5346 ^36(5546(5- £06 4o(56o3664o66(8)-oo6346(5;
COj + HjO ^ HjCOj ;j± HCGj" +
36006000(8)3430 (5636030(550 HCOj~ 0063408 66^0(550 306036(8)660008 366(5036(^08 66834o4o8 3.180 36(56(508 4(5568863o
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75
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<gn63"gc:;)oli 3g3ni6'36gio'b.>'b 18O°-O0) ^cjicjcoolj ljoi<o530''^0» ^a3"C?" fn-infiogGcoiolj
g^iijD^oE^gio'b.ilj ggcj<i3 l».i^gol>o Gigt^oolj 3^)cogj0o.> 3ooj*)g&.i.
r)3^og-gf^o o*br)3g(ooolj 6cT3c^RgGotD.>G iAi ^gscij'JJo 836" g6G3igc:or)56'3o gGiG^onSgfogiolj g^OTijogt^o)
g6G3^'ljbg6ggigcn a)goljgiij:o 6Bg&nco6 "boGiOTjiijoli 3r7E:j6(^o*bi0oo'b Ijoitn^goL ljbgijo<il>l53«i 3o36(^a)'3C;>gioa)
^^"3^3"^ n)G6<no. 36<Ga).>cooi, g.ilj.iggio gibcoti ob «g<>j(®)0, (nn3 boGiXngnob 3cnc;>d('io'bi0oob bobfo^gob bt^-gGgi
Co.igj>g'9o<^gb'3C?o ogo Snejgg'gcjjob g(»)G^oa'3<ni30.ibo).^G,3ia(^,b8 ^ibcocj-g^'a^^o gcoGogog'gt'^iQoob CoijoggGi coojon
bGob g^G3i^gc:;jt*)i.i^o gg(o Stnbgfnbco^.
ibbpicn^^gr^o jm6^03'g(*>i(30ob,g. o. QgG^t^oDiG C°<>J<>3^o(ngb'25[;oo RiiSGiiQgc^gbg^gbob bogt^Qooo
g^Gc;i6ggiob, g.sGbo>"bcig66 ^SbidcjigbgEoo g^bcoi SbncjjDCo (^gG^ggGcob^fo-gJ^Sj-gt^j-gfroo .^Gi^c^obob SgoDncoob
gis3coggGgioa>. boinggcno Gdgt^cno, (np)3j;[;;>obo)gob.>0 1951 ^gc;jb Co-^JoggGog^o o^Gd 6bbtnc;>'g^'3<oo gt^G<gogiD(^6Q06,
ogcn (+) —(ngoGn3g6gi.
6ibr>c;>'3^'3<^o gcoGgog-gt^iiQoob g,>Gb6*bcjg(ni d^cobg 3(^o3^^gg6coo 36n0gboA, G^g^iG womng'gcjjo
Go>g<ooDob,>o)gob .>3ob giggo)gb,i «^'30oc?3^3S2?"" ^ib ^g3cogg, 6.^0 QGnbocoo g.ibjo^ <o63cogGo3g G^genoob
.>bbnco'3(®>'3'^o Jc^bgog-gin^QOi, goRGjo^ j:;o^G.i(nRgGo Gigfocngiob co,ibiboia)gbob ^gbidcjjgbjjjjni.^ G^tno
g(nGgog'j3(^.i0ogiob g^<^ff;jcoG'g<o Gig(^0)<n6 libbcogjj'gj^'gfo gnGgog"g(^)60ogia)6G ^gioifogbob gboo). iSfoog^,
^gbii3c;>gbgc;oo gibpoii ^df^c^cnbnoin jfnBQog\3(*>60oob gi>Gbi'bj:;>g(^ii.
b(8)iGcD6<o^ob bi^ot^ngi^, <^c»)3gc:>a)6G.i0 ^god5i;;>gbc)co,i G.ig6o)ob gnG^og'2(^i0Oob 3g{»<><^gb«>, ^,>63r)o3g6
jwojoo bGoo) .>io<ng, goco(^g (^gG^ggGnb^^-g^^-g^-gcijo .iG.icjJo'bob dgoinjooo) co^cogoGcogbofo^ ibbc^c^-g^-gt^o
gr)G<gog'g(^60O6. 3. focob-iGcogob 'iyoGAco>>C»gboo) (1906^.) 3tiG«gog'3<ni0O'gc;» b^.iGjo6(^(8)ijo ^(ncnhomifo 3ocigb^c;;>
ojGii gcjoQg(*iAc?IS0^"I9'*»^"8cjob 3i<^0bGog- 3i<o2^gGog3b(^'j]G.ig gG^G^ocoGgiogib 3o6^g(^gb gtsGbAbcogf^-gjnjjo
gnG<gog*g<^ii0Oii c°<i i^jGo^Ggb, 3gbiibi3obij3o, D- £OiN L- bo3bp)c;>{*)gioo) (b-g^. 12.6).
CHO CHO

H- OH ^H HO- H
fcH,OH HOH,

OH CH2OH j^Q CHjOH

D-(+)-gc?o0g<oAcjc?g3o(oo L-(-)- gc?O0g<^».>c?cogdocoo

bg('i. 12.6.gcjo0g(<>»c?c?O^'^5"^ 06d6(8>o(n9g(«igfto

Ggbob3og(66co Go^gt^ocjo gcoG<gog"2(6.>0o.i 3g3cogn33o g5b3g6o3gG(8)-j>]j!niTij;oiQ

Coi8(^go0to.i 8iG liiboj^n-g^-gf^o g(»>G<gog'g<6ii0Oob d^c^i Boocjjco, D jo^ L ibcogbo go bigjgrtgmjjoSogl'io
6n3g6jc?i^grtob bo9inj![;;>ngb.ijo o^A.
D-b^gt^gnJoSo-gfo t6ogb dogg-gcngGgbii D-gc;>O0g(66cocog3ocDob 3oG.iO)gb6gg G6g(6o)gbo jo6^c;;>'3(6o 0gG^(6ob
obgwo gtnG<gog'g<6.i0ooo),<6(O06 ^'3Gj0o-g6o J^g^gggbo (-0H,-NHj,-Hal) <go^g(6ob 3<ongj0o.b^o g'^Gcn.iggb-gcijn.i
33^i?)og<>C!J'3<^o biibob di^jjgGog, bncjon L-<oog3o — 3i(60bGog.
bt^-gGgob Go^.iGo •3^*3<ic^c*)io c>(n 6(6ob co-ig-^g^of^gb-gcjo gnG<gog'3<6.i0o.ibo).iG. cn<h 6.ig<6a)b ^godc:;;>gb.i
d^Gjogb g(6o)G6o(6o gcoG«gog'g(6.>0O6,36g(663 bii3oAob3o6co b(6'gGgob Go^i^Go. '3«g6r) 3g^O0, g(6o)b6 jwi o3.igg
G6g(6o)b g-iGbbgiiggb-ggp bo^nbgb^o (bbg^icoibbgi g.i3bbGgc]7o,^g33g66(8j-jrj<6.i) ^godgngbi g-iGbbg^^ggb-ggoo Go^Gob
bt^-gGdob g-gwbg g^iifiGcogb.
3o-gbgjo.ig.ijTo o3ob.i, t6co3 D, L-bob(S)g3ii b^io^jo g63cooggGgb6, g.iGb.ig-ga)(6gboa) i3oGr>3g6ggbob6 jo.i
6.ib?o<6^gcngbob Jo3o.i3o, ogo ft-if^ggg'gcij -gbgj^b-gconb^b ^Gob obgoDO G.ig(6a)gbob giGbojiogobib, (6r)3geoo)ii0
6(6 g66RGo6CD b^(6-gj^-g(6"gcoo 3bg6gbgb6 gcoo0g(o6coj3og3ojoa)6G. 1966 ^gcjb (6. g^Gob, g. oGJnjjojoob^ jo6
3. b(6gcongob 3og(6 '9g3p)0f)6g6bgb'gj»o o^Gi c»)3^og-g(6 obnGgt^oo^ gcoG<gog'g(660oob g^Gb^bjogt^ob "SgjoiJogboo)
bcngijoo Sgonjoo (6g(8)C0(6gb36 36b 3n8(|ogg(6(«>bnb Bgbo "g^cnjogb), (6n3g5^>o0 jo68g6(6gb-gc;oo6 3ncogg-gc;>ob
bo3(60O(no 3c»)jog5tTi)ob •3^"36{*op) g6Gbojiog6bg ^o(66j!o-g(6 6(^co3o)6G C06g6g^o(6gb-gcoo R63G60g5[ogbj::ngbob
*g<g(6r)bnbob g6(ng6Eoob^oGgbo(n. 68(6og6jo,b^g(6ge)^o3o-g(6 Gn3gGgc;)6(8j-g(66^ D, L-bnb^gdd ^3O036co6 6b6j;[oo
R, S-bob^gdno).
3o3jogg(6cnbob tpgboof) bo(6ggco (oog^o b6bj:og(66ggG ^(66co'g(6 0gG^<6oD6G lo6g6g^o(6gb-gc;>o R63G60gc;)gbc>gbob
-g<g(6nbnb6b ^g3joggo g(6o^g(6o-g3gbo(n:
1. cn(6o B63G60gcogbc:oojo6G ob66 •g«g(6nbo, (6n3gcoo0 ^go06gb Jo(66c;;)-g(6 0gG^(6o>6G •g^6coc)j:o
102
 0C!J39gG(^oli 8icj.ij^>o 6r)8(noa>. 86^ic;joa).>co,
I>Br>Cl>SH>F>OH>NH2>CH3>H
2. OT-g C?'^J'^3^^0^"3CI?o r><oo .>6 83(8)0 6^(*)8o g(^o)6io<^o6, 8^^o6
B^3G6(33cj>3ic!^o'lj •g<g(nr)btni.> ^iGo\j6'bj:j3(^35i "DdSO SioooiiG {o^j'ig^of^gi'gcn (83co<o3 aG ^38(0^0180 ^(ooIj)
i(^n8oD.i <00^0000 Gr)8(ooa). 86^6c;>oo)6j«»
CH2SH>CH20H>CH2NH2>CH2CH3>CH3
CH2CH2SH>CH2CH20H>CH2CH2NH2>CH2CH2CH3>CH2CH3
3. (D-g 8gnfog (o»G 338coggo) "Sfnoli 3<^<"8.>o6oi, 8^3^068 iljgo) 6^n8o)6 (oo^bgo ft^G'bbgiggi'gcjoJ*,
d^^oG oli 5^g*g<goi •g«g(^n'bo, (^co8gc;)OQ 83(^ G.iSGiQgcngigci^'b •g«g<^c») G^jn^coo ^^n8^foo GnGfooo).
8i>^^C>oa>ij:o, CHCl2>'CH2Cl.
4. (o<*)c°3li<>(3 jo(^.3C;;>'g<o 03G(8)6a)^G 8co^6<^o .^(^nGgio iBgioor) "gj-ig^ofocogiii tibgii
6(8)n3351j, 8i3oG ^3 'gg^GibjGgcjtni t^joQbgo cot^ggQcogii ((068^^" '939o'^333«^^o) (lj688.i^o
iSob '3g8a)b3336^o). 8j»aicof»t"'^C5»C?*^ giioicoGocoob ^iG^i^coob i(8)r)8'g(^o Gn8(^3io.i,
^gboi^Gob^co, 8 joi 16. •>^gc®«iG j^iiSnSpooG^fng, C00H>CN>'CH0>CH20H.
8.>b ^381033,(^^0 (^-^c^aoGjogi^ Bi3G^o3C?0^0C?^'^ •gg(^)(obna6, Gncogg-ggoob Gnjogcob "ga-geGgigG aSOCJ'^'^O
•g8o(^cobo B63G.iO3C?0^'^^ b.i3o(oob3o(n£n 8b(oojo6G. co-g i8 ^gSmbgggi^o jo6(o8gGocoo b.i8o G.i86j>03C:?3i3S2?o
Coj^GjgologgacoobiggG 8o8.i(«ia)-gco (8)g566gco(^ob g-gdgbg •g<g(o(»>br)aob ^gGoot^gJob Gobgjogoo)
bi^ooob ob(oob 3(nd(oj>nanb 8o8j.(«Sa>'gc::>gaoo), 8.i^oG Gig(^o)ob ^(ojico-g(tf>o 3<^£>'3f>a'3^"^G"'^^ j^joGo^G^ggG
R 6bcna)0 (rectUS - b^col^o), bcopon tn-g oboGo bo>60)ob ob(oob Gndfo^nbob bi^oG.>ijo3cogan
8o8.i(oor)'gj:;ogioa) —S ,>bcoa)o (co^o). sinister —6(^d^i^cn(ho).
3(oo^g(^o'g8gaob Sobgcogoo) (odg8^.>3.i3o jol^iigo'g(o 03^^)'^°''^^ C?*^3'^3^"'^0^c)C? ^'^SG.iogcogagjnrjoDtj
'gojt^fobcoi.s ^bgoo (n-jGdoSjoggfocoioo) 8oo(oioga,>:
0H>C00H>CH3>H.
330C?'^' ^0 '38o(^t^bo Bi3G.>o3S?0^0C?'^'^ .i^ndo. m-g 8obo b^idotoobdolop) 8b(oojo.iG ^ggbgco^igo)
D-(^dg3^636b 8n5;;og3>g{;i^ob bo3(^o''®'' 8(*>jogj*nb, (jotoiigo'gCoo G.>b3o(^a.ij;oob 6^0080 o^Ggi.> R ~ 3(*)Go3oa"g(o<>Ooob,
bncoco L-(od38g63.>b ?g8a)b3336*3o - S-3toGgoa'g(^<>0"^^ (b*3(^- 12.7).
COOH COOH COOH COOH

OH

CH3 HX

L-(+)-AdgS^iigi (S—o'bn3g<^o) D-(-)-<odg8^3.> (R—obnagtno)

(2S)-2-3oco(^nJbo3t^<o3.i68^.i3.i (2R)-2-3ojo<^>c»>^o 3(^»n3.iG8g.i3.s

12.7.<<idg8-jd36b gGdS^omSgi'igan

^gd-g^^iaga-gcoo^,6^(^30)33,b3(^b3ao .>(06 8r)c:ja3-gc»3aob,.>(o.>83Eo (go^gi^iob 3(^cogjo"0^"^ bgc^b.^g'^gcoo

a«>8(nggGgaob.ia)3ob. lidobiitngob ijoGoSG-gco aincngjo^g^^ nbg (^f^8 -gdotonbo 8>i86do3S2?3^3C?''
(Bag-gcogaioog, ^giCoa.>loob .>(^(080) (jgggoo) anm^igbcogb, ^gSjog^ 30 b6bjn3(#>6ggG B^SG.^oaCJO^OC?®''^ •g«g(onbco6ob
8o8iog3<oni.>b. go^gloob <gn(^8^cogaob brX^O^OCJCoO^-^ G^b^ot^biicoob ^ofoi^co-gi^ .i(8)n8a>.iG
(TOiig^a^oCoga'gcoo 8t>8G603CJ3<^C[J3^t^b "^diboDtiG, (nna<*>(^0 "bgdcoo) ^(ooGo^Ga, .>8
(ooobgo co-g^o -gGcoi ogcob. 8.ia"^C?"'"'^C?' D-ac::jo03(^^Cj{O33ojogo .^^.^(^dngigG 3o(o3gcn a"^C?'^'^t?a"C?0^'^^
^g^iEnbiCoob .>(8)co8ob.i {o^i Joco(#)r)jbo8ga)oc:o-g<#)o sca-ggg^ob .ijo^ocogaob ^gogcjoo), 8gco(og a'^C?'^'=»C?a"C?0^"^
joiocob 30 *3032!?"'^^ iocD(^)co^ocoob6 £».> Joj:ot^>nJbo83a)oco'g(^ ^O^C^Ob ^'^'i^C?3^'^30^
GiiSG^ogcjgbgcjO'i •g<g(^(obr)iob Bg3oo(^3aob doSil^oo-gcoga^b. i8 ^gdobgggi^o oao gdcnbaggti bib.>(nob obloob
dcodfo^oiob 8o8.i(oa)*g{»oga6b:
CHO CHO CHO

H- OH HOHjC; OH HO CHjOH

CHjOH H H

ioJ^ggCjo a"^'^>^£5b"C?o2>-> 3gn<(>g a'H?'»'>C5a<^C?0^'^

(2R)-2-Joco(()r)jbo 3<^3.iG3g.>3.>

103
 a6o^3Ggcor)36G GAg6of)0)6 anpngg-gsnogiolj •386i3cjgW6 <oi8cogGo3g 03^6^^
^30(363^. 8ia)a)3olj G^gfognolSnagt^Oiolj (^io0b3olj 3680003513^ bjogii 2" (gcot^S^coooo.bito^Q n aocngg-gco^go
jo(^>6cn^6o ooG^^ogiob <o6oj:ogGcoi6. -38506 6cooGo3Go1j, <^>o8 ^03 gg8oob3g36^ ^gb6dc:oco b(8)g<#)goo*bco836oo6
(^O0b3o 68 bocoocogbg G63co3bo6.

12.3.2.2. aor)80<&<n0t)c?o o'bnaoi^ioa

a-joo6b5g(^gco8gfogbob 36<o£o6 6(^'b3iobb 7t-i506b^grtQin3o<«)oSo (b(8)g(^>gcoo'boo8g<^gbo, <no8cogbo0 ^oo0631j

7C-b86'b). j:D06'b53<o3n3g(ooob gb 5o.^9ib6bo6oogigc:oo6 6eo3gGgbob6 506 86000 G6^6(^8giob6oo3ob (86b b^66jo
(3ob-(8)(«)66b obro3g(^o6b60 •3^<*)CO0^0^)-
7l-5oo6b5g<ogo8g<og5b 366BG06 6(8)co3oo6 3co<oob bSgiob g(#»ooG6o(^o oo668o8cog3(«oroi6,8635068 B63G6(335Eogigcno>6
36Gbb363gb-3coo bogiooocoo 3^85063346, 60b 36800 oboGo b5g<^Ocoobo8g(og4o 65oo6G. 8go(^g Gbt^og, 36oo
9"C:?a8"3C?0^^ bo8g5<ooob bo4<^5ag (805033-350340 6jo66so«3(^o6) jo^ 680^08 7t-£oo6b53<ogo83<o34ob6oo3ob
368o(oo0b35oo6 3G6G^oo83(^34ob 6(^b34o46.
(^O06 0508630 4834000 36008683000068 506363^0634-350 86b^646co6(8)o834oo68 bb36co6bb36 6^080 68
6(8)o8oo6 3ia*3«go«^ 8686035034-3500, 03383436 6{oGo^36ob E, Z —bob539«Nb. 7C-(oo6b5o63o836o, 609350^00
-3<g6obo 8688603503450340 (86886035034350006 -3«g6obo46 368ob6b{036346 o8 35C:jo9o55f>b 6030000 60086000,
6o)8cj)ob 6^(^800 -3^36500055 3363^0655346 006863 486boo68 855366 86b*9o646556^oo8b) 0068630 48ob bo46^3ob
360) 8b663b 85534663004b, 655080^8346 Z —bo84<o5oooooo (3368. zusammen —3600655), bb36556bb36 8b663b
855346630040b ^39oob33363o 30 —E-bo84oo5oooooo (3368. entgegen - b6^o8665595533oo). 863650000655,1-46008-!-
83oofojbo-2-^oo63oo36^o 4063350 86b^o646556(8)0o9oo68 3<g6oobo 8686603503435006 46oo8o, boo50fo 83oo63boo68
—J500060. b^oo6355 86000 360003600855346630046 368b6*b5n3663b o'boo936ob b6b3b:

^ci
c= c c= c
CH3O CH3O ^ ^C1
Z —o'boo3g6o E —0*8008360

0060 7t-5506b^363oo836o5568,83335034603,83(8)0 003680055086803360 85536655004000 E-o'boo936o 36800068336,

6655368 86b^o 8oo035ooo4oooo 8688603503450340 bo3603^ 3<i3<^ro 556^0063435006 36oo8683ooob6366.
7i-55o6b^363oo83634b, 60030060 ^gbo, 368bb3633435oo <30*80336-^080360 0030834340 3668806. 863650000655,
43^385508^6368 (ob. XIX 00630) 0060 0*80083605568 865030883636 (tppm. 131®C) 36b3634ob6b ^66800^808
00350-36 68305560558,36^8,6oo06 3386683636 287®C), 686500030-^ 4o6oo4343o,666300066 035150(03468
66 36800550b.
75-55068(^3630083606 338355346 8663650 4005003836 863600^0. 863650000655, 63(8)06005008 (30(8)68060
A) 9005033-2506 ^300638 6685538083 006863 486b 556, 68680068, 33352^6 86003680068 868860350345034b ^6688-
85530086630046 336306:
up H CH, H CH,
^CH, I I 3 , ,3
CH,OH
cr"

0*800836008 68 ^o4b 0050.(8)6668 0*800836068 (08350. all —333506) 3^00553436.

438346^0 30J600 b'ao6655 E — 0*8008363406 36360350343500, 003806 5oo4o5534ob 3355338o5ooo46'3o
a3b355346 33^360 0808003680 9^63g4o (ob. 26.1.1.), 6008350006 8005033-25034^0 3335:56 006863 486boo68 36008606
868660350345034b (1^365046556(^008348) 008-85530086630046 336306.
H H H H H H H H
<___>=< >=< COOH
H3C ^ch; ^ch,\h,''
666(105500833636

104
 o'bnSgf^oo'b gl> ^o3o rnnj-Qob olroSgrtoob biibgjn»^nj3ogio0)i.i QScTiojioo. Si^coiicnoi, Z-o*b(*)3g(^o
a)g<o3cocDoGi3og'g<o^Co G.»jcj>g56co66 bgc:;)b6g(^gcoo, 86a<^is8 a^iggiob 68 g(»>(^8oa) 6(^bgioi6 bgcjb •g^gcnib
C;>o3oj:ogi3o (306,3gb6i63ob6jo» "ajS^^OCoob 8g8b<o666^ G^b^e^^giEji^co-g^o (^^fioog^cjgbob Ggcofog-ggj
b56-g^5'g(^>6b.
(3ob-(8)(^6Gb obn8g(^o6 ha^cn^o,
00^08650 i8ob ^Gicofogogfo^fo, 68^b(^'g^gib w^gob-gg^cj iio^gGgib, <oob 56800(3 B«i38603c:jgic:!?O^
g6Gc;;>6g£ogb Qojgoob bob(^^gob g(^o> (Qob-obcoSg^^o) 6G bbg6co6bbg6 (^<^6Gb-o'bco8g(^o) 8b6(^gb.

12.3.3.3b390<«)0 nfnd:>6;3C? 650<o0)0)b 8nc?33^c?0b0b ;>Q663nb5b6

850) bonc?(n8ot)<i^ 5d(§>03nb5b an<«iOb

(hnyn6(^ "3^33 6150G0W6, QSiG^ooast^KJii (goTjoj-jjA-joSogtSio mgolioiQio Blja-^gljcw, 8^3(^68 -aecoji jAgcxngAcjolj^ciSncr), ogoliO"
68336^0 <Ho36g>g6r)io 3flC>>J3G(O0^6 in vitro rtgijooQiSo, 8i'9o6 (00(36 invivo qIj 663(^0)3^0 oBg61j I)(8)3(o3oli5g(3o«go3-3(<)oi6lj.
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2-dc>oo(^-2-3go)02ob"g56Bob (og3o(o(ncoj2!J'*^^f^^0^^^ 8g^66ob8o!

117
 CH, Ggcij
CH,
I U
CHj-C-CHj-CH, CHj-C-CH^-CHg+Ci-
ci-

CH3 CH3
II H0-+CH3-C^CH-CH3 CH,-C=-CH-CH,+Hp
H

Sn8p)imo3t)C?\D<*'" (E2) 3oJi6o'b8oo) aoScooGifognil Q^[ooBo£o(h^oh ^g^^Qogio 3o<o3gc:;>.ijoo Cbcoaj^gen

agcn^g-gcno) 3ij:^r)agG.>c:og66giolj ^6 li3o6(8)giolj 8n6o^oc>gnioo>. ^8 (^g.>j(306o>i ljoBjA<ng jo^angojogi-gcu^oi G-gj-
Cngcn«goc><3<no <ng^aaS6<^^ jnBQgG^tn^OOd'bg. .^GiljODiG, lj(8)icooi*bg G-ggcngnojoc^o •3^^cr)og(<^a)j8g^:ogil>
P-G^b^ofni^joolj ^gj>c?i6£06(8)n8o)6G. E2 GgJiGolsaoa) GoGcooGit'ignili, 8j.3^cnoo).ifo» gof)oc:oi(n(n3ocoocoj>G gwojcijgGolj
lioGtng'bo'b 'l>3o<^^b'bG^<^o'lj o^GAniob^l):
HO-+ H-^CH^-^C H^^Br [HO ^•H-.-CH, .CH,-..Br®"] •H20+CH2=CH2+Br
(nn^cn^Q bgano) o>cjoGo3Gj>, gcno8oGo6giolj co<> ^-gjcjgngocn'at^o GiG^Qgs^jgioli (^giJoogio ^fhrn-
8iGgo)b "O^OS^* 1963 ^gcjb <o. 3o6bcoGob 8og<o ^gGncn.ig^'bgb'gc^io bnt>(8)0 <<ibocno 8^03-
Oiobo coi ^^dQgbob 3(finGon3n (ob. IX a)J>go) JfoGg-gt^gG^-gc]!! (^gi^Qogi^o (^g^ggG^giob bgcog^Qo-gfGniob
OTigobgi-g^o "Bggibgiob b^^-g^cijgiib odcogg.>. .i8 36oG0o3ob m^G-ibGico, bob(8)0 G^^ggio •gggoD gcon(^cooGo6cogb^
bob^ ig-gdggiOTJkG, bcojsjjtn (^iogoo 8^J>gg<!io —(hho^ <g'3dgg3(nj>G. i8foogo>c°» <^O'i^0oob 3(^co0gb3o ^b^jjoo iGgbob
^it^GnjGGob •jgG^t^o c°'^9t*>gocogb"2c;;>o6 big2»b(8)(^.i^ob6 '^g-iagG^ob <gi(oj3oniooD bobob^gbii bo^niojj^gbg
(Obt^. 15.1).
ybt^ocjo 15.1. bob^o coi(^jbocjo G^dggbn (gd Qigdggin

bob(8)0 6iocjo bob^o Aiocjo

H^O. HQ- -SH, RSR, RSH H^ Na^ Ag\ Cu^
ROM, RQ- H-, r. CN- Mg^\ Ca^\ Hg^"
NH3, m{ R2C=CRj AP^ AlCL L
RNHj, RNH-
ROR, RCOQ- y-v
c'-' F- °o°
^"3-^c?gco'3<<io
Br-, CgHsNHj Cu2^ Fe2^ Zn2^ R,C^ CgH^

eocogn(o(3 Gngg^Gocoo 0b(nnc:ooco.>G B^Gb, bob^ '3"3'^00^I* ^.i(^3n.iCoggGb G^o^g bcoGob, .i6.>3r)-
COiX^obgitifoo .>(8)n8gbo .iG orjGgio, bnjjjto 6boc]o 8^.>ggibi j2o.i '3"3<l00^b —'3gj:o.>t^>gioo> joocoo bnGob 6{ogoj::n.>cD
3n5[o.>(no*bgbiicoo .i^coGgio .iG onGgio. G.>a'^C!?"'"'^Cs» 2-i(^cnG3^n36Gob Grmogg'jg{n>^'9o b^ifng^jyon 0gG(8)(^o6:
G^ib^ot^iicoob gE^;Jgj^^^c^^oc:n'3(^o 6(8^0080 co«> Gndto^go ^gcoi,yjo.i^n3o (CH-G^.ig'jjt^o
QgG^too). 3(»>^gcoo <^g«ia0^d>^^ (8)o3ob 3obgcogo(X) ^godj^jgi^ ^6<oo36fGoD(»)b G'jggcogogo-
CH,-CH-CH, CJIj-gtoo B.iGi0gci>giob ,iG gc:;)o3oGo(ngbob gcoGg-gi^gG^-gcijo ^ogi^QOi. 'bg3r)0f) 3c)gg.>Gocjo
♦ f Qb(^05;;;>o£o.iG B.3Gb, (^oG 3t^n^(*)Go Gogg'jjjogGgiA bob(^ ^^J'^gg^b, bcocjjn G.>b^<ob.^coob
Br®- H
2-4(^n33<w36Go
C0«>C®gboa).ii:o C0.i3^b(8)'gc;>o .>(8^080 — ^<^5S;jgco'3<^, ^g£o.i(^gboa) (niocij
g.iGr)GcooG.i<ng,<niog;]oo G'j]jcj>g(n«gocjob ^g^gg.>
i.>j:?ob gc;>gj(8)<^co<goc«*2(^ 6(8)(nG'bg,G.>3o6 (^coqa bob(8)0 G'j»)js:j>gn«goj:i;oo (d5j;>og<oo •g'gdg)
^OXD^ggb 3<onj§nGb. ^Go^nG, 2-i(^nG3(^>t»>3.>Ga)6G Gi^^o^gGob gojopjjjii^ob g(oa)og<^o)^3gcogbob6b (CjH^O" bob^o
3<n(»>^r)Gob (bob^o G^.>g.>) Go^ggg^.i co6 fog^jyoi ^6g6 gcooGoGoiogbob gbocn:
CH3-CHBr- CH3+ C^HjONa CH3-CH=CH2+C2H50H+NaBr

118
 6,>^6o"38o1> go)oc;)0)0(»)c;j«>^o^ Sco^gjogiolwtj go)oc;>o>or)cj.i^-ot*)6o, (^coSgcijOQ ^ho^a ^'g^gij'Sg'g^Sjgglj Bib-
Sofniijoob OC:J9^(5)<^t*>o30cn*g(^ 6^o8b 2-i<nr)83<^r>^6ob Sncugg-gt^^^, (^ob ^(]Cog5«>Co«^(3 8nbcogi.i it^(*)8oso-o(»>Gob
ga)0{:;;)0)on5:[;;>6(^-ocnGoo):

CHj-CHBr-CHj+C^HjSNa CHg-CH-SCjHs+NaBr
CH3

a) tjd6a3i-dc;io3Q6oinf> (*>gAjj(3ogbo. .>c;>6o'36'g5:^o <og6^ogio <QC>^cncnfo^i, g.igt'iQgcijgb'gcijo o^Qb^co (n6^66o'b8^

to^ ^gb.>i.i8obo o3gfo8g6^giob.> to.^ oiB^roiobib 8o8coo6^<ognib, gb <og<>j(3ogio i<o.>g(oa)bgcj;)
oJBgi^ ^O^fiog^ oiggi^o.

119
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{06 ^a^crji^b aiioK) bna^ c„h„. &>b^^a^c?^xooi^ co^ajfx" ^ ssa's^-*?
- (c^ 2^^530^) 0W3^ G^bM^a^CJ^Oioco. ^aoc;. 3j;a"3g'^ ^J^Goio, .>c:;.jaPa^,
^a^oGgSo JD^ ^ao6gio,bncor) 3gn(^)gb - QOjcon^a^oio .i<^)na>(8)^o G^b^^a^coi^aio (.vt^gpgio).

16.1.5C?J660&0

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(o.>3o>5gaoa). '^SE^d'i^giob jr)3r)c;>toao-3<^o fooaob 3o(^ggcjo ^ggtno SgOTiiGoj*, .i3 (^ogb b^o(<iJ>£o 3go)j>Gob
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C,H, gtn^Go C^H,, 3gG(8)iGo CgH,, C^^H^ •3Bc?gg^6o
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HHH HHHHH
III I I I I I
H-C-C-C-H H-C-C-C-C-C-H
III I I I I I
HHH HHHHH

CH3- CHj - CH, CH3- CHj - CH^-CH^ - CH3

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sp'-doit^ocoo'b.iQoob a'^9(o aSOK?*^ 66b3o<oi.icoc>^co3ob gc^gj^t^c^G-gcoo gcoG«goa'3<OiiQ06 — ls^2(sp^)^-3g(n.>Gob
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66b^o<^iico6(^(o3a).3 a^'^dgpino j^ii^go boa'b.ia^^O^'a'^ «gco(^3,ib oingbb.
^gogiiGgiob 3co3mcomao"3^^ tooa^o •icoa^'SCJf* "^d3^ o'b(o3g(ooob gfoco-gfom b.Nbgb — JC-i^gob o'bco3g<oo6b.
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.>36ba>.^G, G^b^o^oi^coob .i^co3cn.> (^o^bgob bt^coobcn^G gi^oD^co 3i^cnn c^oQbgo 3.i^"j]c;;;»cobb. Gia'^CJom^jo,
3gG(8)iBb a'^<^GGo6 3 obcoGgi^o, 3gJb.jGb —5,3g3(8)66b —9,cogg6Gb —75, bcocijco gogcob^Gb —366319. Jg^^Go
9go3cogi,> tifobgicoifiogb ^g9£ogao obmGgfogbob b.>booD:
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CH3 CH3
i) CHa-CH-CHj-CHrCHj g) CHj-CHrCH-CHrCHj
CH3
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CH,-C-CH,-CH, g) CH,-CH-CH-CH,
CH, CHj CHj
120
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121
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R- + CH2::CH2 ••R:CH2:CH2-
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nCH2=C-H —CH2—CH —
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R-C = CH+H,0 ^ R-C = CH, -^R-CO-CH,

I
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R-C=CH + NaNH2-> R-C=CNa + NH3
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132
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0C:jad6'^"^'3C:? bo333<#>o3gb,<oob a-^Sf^G 0^ •33'^^'^^a^OC?" 6(^o365'3e> io(^a>39o,a^6b63"3o>(^>gioo) go
0(^0)0- £06 36^6- 3£0a<*>36<0gcoa69o, (^69£ogG6£o3g 3QO(O£0gi6:

6jgio6G a^9t^9t?oG66g,gc>gj5(^co«goc:)"36o G6^ocn6gob 93^336 93£06<#)3ioo) a'>963c::>£03i6, btocjo B6G6Q3c:»3i6

a6Gbo(o0O3c;>£O3i6 II (ooaob B636603co3icoob 3o36(^cy) 335'i-9t®a"®'^^0'^^'^^""
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369o6 6oq6 3356-jcjo(oGo5(^tni3G'bcoc:oob 3ob6£ogi6£o b6^o(or)6 Go5<^>oi3Gbcojoob (Go^fooj^a^'S" <^oaob
B6366(33c:;>3igc;>o6) jc:;>co(^o<G3i6.
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6<#»6b£o6r)b 66 b6"3C0j0Qi6 6bbojo"35"366£0. •33663c:>3b 636^00606 36o£0"3^53b9o g6or>io6r)"3c:o6£o aS^SC^O^"^
o6o)(*)-, 335"^" 3666-o'br>3363ao.

137
 XVII 01)30. a6n3363c;n3)6n anon-
3nc;nQ36dBn3An G33Aoi3in

17.1. 65ba0(n6d6C?55C?0&0b 30C?(nndb06560(naObO

6,ib^o(o^a65::>i6togiolj Scoc^og-gcijoi^o 3(^00 .^6 <ni8jog5o0g ^(8)n8ob JoiD^njbocootj %^'jQom

RiG^Qgcngaobilj 8oocjgb.> 6ib^o(^^a.>Coij>Ioo)«^ Joco6n^o6.i^.>(<i8gio. b3o(o^gio - 6j>g(ocngboo>,
(^n8gc:>oD.i 3oco(ocojbo{2;)ob ^g-aG^Qo-^i^o o>cog.i6ob, o^jci^joGob, o>c;>go6ob,
Qojcon^CogiGob, o>(^g6ob (333'^^°"°^ ^8ob Sobgcogoo) -^<^^030^
•>C?o<g6(8)-gi^) (B^2^;3(o, •33^3<n), ^c:?"0'^3C?'3'^ 6<nr>8^^-3C? b^ofo^gbb. cn-g JojofBnjbodjob
bg6*bnd?ob iot^oogb 'a3'^3^"^E?0^'^' 8o>^o6 ^bgo) Big^ooDgbb «ggGc»)c:jgbo g^c^jogb^. Joioi^t^jbodjob jca'a'gg^^ob
<^,inj:og6{»)b6 8nd?03"3C!J'^^o bboto^giob^ co-^ <3g6ncjgbob ^^r)8o6Bcob.ib ^^Btibtx^nigbb. .><0^3336 g^no)-, n6-, b.i8-
Co<> bbo^B^gbbii fo*^ ^Obr^Cljgbb,

17.1.1. b30(iiǤ>0a0

bbofnj^gbob 8cocn03'3C!!JO^^o Joco^nnjbodjob sp'-Jobfoocoobgi-ad? 3j:o^(*)8663ni.>9o

BcnSgBjcj^St)^^ C?^ ob(n3grtnd. (^«>co"3"^C!?'3'^"^'3^dG""3^" Gn83G3dJ«>(5)"3^^®' bbofo^giob biibgcn^ncoo^*'^

^6fo8coj:o3g2>'i 33bib.i8obo (^.ico'^3"^Sl]?0^ob jW'^b^bgdjgbob.i^iB.
CH3-CHOH-CH3 CH2=CH-CH20H C,H,-CH,OH
o*br)3(^m3odJob bbotnj^o .>dJ0dJf)b bbnfo^o bgBbodJob b3o(^^o
Bi>B<>Q3djgbn(no 601836320 b3o(o(8)gbob bibgco^ciCOQ^'^ o^i(hScn^i> ^3b.>i.38obo BibSoio^g^cob^coob
b<>b32o^cnjD02><^'b3 b"a^oJbob —ngoo io6(ncn^ocn. .>86b(n.>5, 8oi63.>(oo 2£>i53f>b co*^^^93'^>^ bjogb-i 08 bnconcO'^S,
6n83cooi»i6j>0 'a'S^f^ 6b5:ot*)b.3ii Jocot^cijbogoob j^a'a'go co"^ 8o30)0(n3b.i o>8 'aj-^^'^bgBgcoob
8co3b^(^3ob6.

CH3-CH=CH-CH20H CgHj-CH^-CHjOH CH^OH-CH^-CHOH-CH^OH

2-b-a^gB-l-ndjo ^"^ggBofogoiiiGncoo l,2,4-b'a(5)<i6^<6ocid)o
CH,

CH3- CH- CH,OH CH," CH-CH, CH,- C- CH,

I I I
CH, OH OH

2-8301020-1-3<ocib^6ci2]!Jf> 2-3(or)3.>6n2!;jo 2-830i02:i-2-3(on3.iGoi2oo

(o'boib'g^o2oob bbofo^o) (8301(0-3foc*)3o2oob bbofo^o) (83bi8-b"g^o2;iob b3o(^^o)

boi^ b3o(o(8)b 33801(^6360200 otjgb (8)(^o3o(>2:i'a(oo b6b32:i^oij:o3b(>, 8.i3^2]:>oor).>co» 83(ni6oi2:ib bob bbo(^^b
"a^cocogbgB, gcn^Boicob —joSf^^'^b b^o(o^b, boi2:ioi l,2,3»-b(6oib66^(^ooi2ob 30 — •
oi(^ii^oi3o66o b3o(o^3bob — co""C?3^"b 3C;^<ibo<go360o^b -ibcigBgB Joj:o(^o^o2oob 2d3"a^3^ob
•a(6oio3(^oi8co3b.i(o3oibob 8ob3£03ooi. oboBo 33od203bA 'a3i33o(^co0^^c?^0^ 9o'boib32o 66b3o(6b6d'i^oi83bb (303-
joooi2ogbo) ^6 3(ooi8,>53oiob63i6 •a«g(^f^ "33^06 (Ij^-joooidigbo, l,4-cooci203bo .>.3.). oi'a80i,
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d^3^33o(^3b"adjo (a38-coo(od>3bo).
bbo(^(^3bob Joi8co2ooiao'a(^ (^o^ob ^33(o3bob.ioigob jO'^^'^b.iboiioigbggoo.i 6.ib3o(ob.id'3C?" 3i"^^3obii fo*^
3oj:o(6(ojbo2oob j^a'a'Qob .16 2ig(^«iio" b8ob 3cogbi(o3oibob 0*60183(^0^:
CH,- CH,-CH,- CH,OH CH,- CH - CH,OH
^ I ^
CH,

138
 CH,-CHj-CHjOH CHj-CHOH-CH,
CHj = CH - CHj - CHjOH CH, - CH = CH - CH,OH
o*bc)82(^o6, bcoc;;»c*>
^g8(33gcn b^ot^^gbb — o'br)8g(oo.i
?JobnjX3<«io (ngobgbgbo. C, - C„ b3o<o(8)gio boo>bggio.i, bocijco 3tn3t»>c|Tto30"3(^o fon^ob 8^c>^c::to
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bbG-ijoni^ SGo^gGgc^cigGij:© G^o^fogii. bbo(n(8)gbob •gGt^.^ggigbcibob.xngob coo>86bAbo.io>gbgE;>o6 3^(030 bbGctconbi
Dfo3iG"3c:i 3.i8bbGgc^gi'3o. 'Bgb.ibiGob 6ob^o(<i^gAc::>b6Cogba).iG 3gcBj><<igboo> 8^010 jcocjdiob^ jd,> Eo-gjrjos^job
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^8 "jjgiG^bgGgcicnJk (^o^bgo 3nc;>onc;igb'9o -3^(^01 8g(8)OA, bciscio8g(:«>'3S[:;jo (8)o3ob ibciQo.i5giob ^i<i8oij8Gib
{06,.ijg{06G 3^8co8cooG.i(ng, ^8 G^gi^wgiob bobc:>6G(8)ob6 fo'acjocnob (8)g83g(^^(8)'3(^ob bfojo^b 3iG6bo(^>dbgbb:
•^OCH^CH.O^ "'^'.OCH^CH^O^|^^.OCH,CH,Os,^..
jjo8og«>ft (ngobobo&o- bbo(o(8)gaob ScicjOdtJCJO^^" ^go8c:>gbi 3^801330101 ^38(0330 b^^g^joooi ogB^f^gio:
OH-8363'3(no (3gG(8)(#>o,<i<i8gcj>o(3 0-H b8ob S^i^jicio boicji^nbob 3^801 3.iG^3o<ioibgbb 3<^ci(«)0iGob 8oi^33g(8)ob
ggb^dcogicicibob; G-33c»gci«goci^(^o foi n-g-gdoig^Go (3gG(8)(oo - 3^-3G6^oc:ogbgc:io oc:>od(8)f^£n6-3c>o ^ggos^job 8^oiGg
-j^G3bi{oob ^50180; ocjoj6<^n<goco'3(^>o ogG(8)<io - a-Gib^6ii{oi(8)oi8o,<noi8gc::>bgO 0C?0d6^"^"3C?" boSggt^iogob
joggoQo^o 368t^^3g-3c:>oi 8gboibgc:io Jojo^^oi^ociob jCb'S'S"^ -I-0<30d6"'"» p-CH-8-]A3-36o ygG^^^o,<00183511^00
C--H i8ob 3coco6<oob^0o6 3^Gbo6oib3a'3c:io.>, 63<o3o)33, 3oco<^)oijboc::>ob 5sa'3"3"^ OC2?ad6^"^'^dOO'^6^^"3C?f'
^^gCogGoo).

GgjCjgcngoej^f^o 5* n-ggdmgiGo QgG^i'io

R—CH-^CHj-^O^-H

OH-8^A3g<^o

^833i<oo 6ciG.i3oiaob 3^801 bbo<^53bob oigobgigio d-bcibg 8<o636c:i<g3(^oi36Go.i.

b3ort^,g&oU a-)d3^rto (SO ^bot^i^gbo b-gb^o OH-8g033boo ^(^igGb^gcoob Boh^^^ocn joo
bob^o a^oggbo 3o<^>b(oGob 8ob3(03oo). 08050180-H a8ob 30^3335^ boi^Qogcojsgbo oj^o-ge^o ^ocnnS^oh (Na,
K,Mg,Al) 8(1^83(03600). <^)3idoo^ o63(^ao-3(si^(o 8o3(ooG6<#)3oibb. ^8 fo^cnh 3^800301036 ^gocob^coo (06 80051366
6C13030CI650:
2R - OH + 2Na -)• 2R - ONa +

aoiigb-acio 6CS30J0C165360 (6(2i3ojbo(036o) '^(ggtio,836(^)0 Go3o)o3<i3636o6,(^)o8ci36o0 ^gccjob 80^83(03600)

•^(53oc^6(o 3o(o<io(iio'b(0366:
RONa + HjO ->ROH +NaOH
6c>3odoci6536ob ^6<#)8oj3G6 800) •3«g<^o 6(0305:16(0 b(O366,(^60 -gge^o d^oQio ogobgbgbb 63(03Gb
b6o<i5o (ob. XIV 0)630).
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3Cio3ociob <#.36^006 G65(#,o-38o6G 3o<#>33(rio OH-3i3-)gob 8oG6^o50?ar)6oo 6(030(06(0 ao8(ooG6(^3o6b, 863<#>68
6656o-38ob ^38(03080 80^)83(0366, 6GooG'3<#)o 0oG5<^ob 3(03j5<GoG(ooGo<^)«3(oo 3635o:>3Gob 3680,'3«g<#)o bob^
30(^0636^0 60(^003(0(0366:

HOCH,CH,OH
2 2
+Na • HOCH^CHjONa _H^
NaOCH^CHjONa

3O0-(ooo{oi)<^>o o}<?>6383G5ob ^38033(00 305000(0360 bbocigGdob 3o(o(tf)o^o(oo6G ^6(#)8oj8Gob co-^^%o

<g3<iob j3(o65"3(^ gt^adcjjgjbgbb:

139
 2-
CH20H
2\ + Cu(0H)2 + 2NaOH 2Na^ + 4H2O
CHjOH CHp OCH2J

gl) <ogJ>j0O6 a^SnoggBgii .icijGo^G-gcno 3(»>c?oncjgiol> ^cjSn'bj.BgBico.

3^63^0)66 ^gio^t^gioo) ^{53oc:>ico •gfioogfnojagcogJtj Bbncjcoco Bo^osgcoicoo b3o6(8)gio.
fog^^Qoob 3(^c*)co'3j(8)gio gogt^gioi!
(yc
CH3CH2OH + H^SO^ CH3CH2OSO3H + H3O
8gn(«>g"3c^o 3gb63g'3c;)o b^<^(8)gbo'b 3n3o6£o3gi3^bo)66 ^.^Qbgcngbobib 8o3coo6,i(ng(nib coo^ocot^^^Sj^yoob
3(^nQgbo co6 <>5C;J30^0^ ^ii<n8no^3Gg6i (ob. gc;>o3o6o^^gbob <og->j(3ogio)..
3jn>oQg(or)c;>ob 6o(^(no(ogioo) 3ooc;>gi.> 3obo ^<oo6o^(n6^o:
CHjOH CH2O--NO2
CHOH
1
+ 3HN0j "'Tun
""^"2^
°'^> CHO—NOj
I
CH2OH CHjO—NO^
3ocogii»jj;™> ^c^cojo-g^^b, <^co3gc;)biQ, b^ofo^fo, 6o^(^(n3c;»oQg(^o6b "g^c^fiooboG, 3'i9nogg6gi.i
{oo663o(8)ob co^b.i3'b.ijoobc;j«it®. •^9'^30 3o'b6giob.>o)3ob ob3.i(^gii QoocugGgcoogcof^ob cooBojSjfo^^o. gc^oQgtnncijob
^(^o6o^(^.>(^ob l%-oi6o b3o(^^bb6ii<oo 3«^9tno3gBgi^ bobbc^d^(^E;j30^f>^ 3.ib.i<g,i(^a)r)gbgcj> bi>^.i5:2;>gi,>Eo 3^3'^30
b^gGngtif^Coo-gfj^o '9g^g3gbf>b6b. biSggi^Giic^co 3<og3ii<o.i(8)gio bgbj^iigo 60^(000630 Go^Sjfooogj^joQgtooGob
ifooocoooGgof^gbgjIoo (bi>63<^3{:;;;)030 GcojBgcogbob) Sog^ocog.^ojbgfj^'g^oo <gco(^3gio6, (ooo3ji[;;>g<!>b.iQ oggGgbgG ^'ggoob
o'3g3og<^o jo<><>3«>£oobob b(8)gGco3.>(oj:DO"gc];>o 33^033bob ooiigofoiG «>b.>Qoc;>gij;;;|>j»co.
^.i(oio 3o(oggc;>.>j:oo b3o(o^ob Jt'^60g6(^(^o(ogi'gc:o ^ro^ofocoBgig^booiG ^-^Qbg^ogbobib ^.i(o3cooj36gii 3i(o^ogo
ga)g(oo:
H SO ITOT
CU,{CH^)fiH + UO{CH,\CH, CH3(CH3)30(CH3)3CH3
3gro(ogg5Tno co<> 3gb.i9ggcj|io b3o(o(8^gbo ^3 3o(ocoigi^ •^C!J309ob«>t® 3.i<^co.ioj36gi6.
36(oico63g^3gio)iG, ^0oc:;>3.iC;>co3gGoi:ogior)6G £oi giXoicoGBg^g^ooi iGJoj:o(oocogi(n,bG gfoooogfoooJBgcogiobib bjogi^
b3o(o(^giob ^0oc;>o(ogi.i (^a)"gc[no gcng(ogiob ^6fo3coJ3Goo):

C,H,OH + + H,0

CHjOH + -* + CHjCOOH

3ro6o6ocjO"^"<» SoScooB^yiO (<>OA;j0ogbo. b3o(o^giob BcoG^^ocogcoioof)

3o3coo6^(og 3(o6gj>cno (og.ij0OJ> bco(o0ogcocogi.i B-ggcogoogocoob 3og(o a-Gj>b3o<^i6co6^co3ob (gc::>g;]5<^<''"goC?"3^^o
Og^6^o) 3o(8)03oa>. '9oc?oa^co bjogi^ C-Ob8ob 3^^330(8)^ joi 3oco(ocojboc:oob 3ca'g<3ob B^G^Qgcngi^.
b3o(<S(8)0^o -gt^ooog^ojagcogib J^coco^gG^g^cniiCogiooiG ^6 B^o) groG^gG^foo^^gi-gco ^30>c:;>bbG.>6gia)6G:
R-OH + HX ^ R-X + H3O (X=I,Br,Cl)
•^CjGoBG-gcjj fog^j0o.>3o gggcijibg Bg^ ij^ogooij^b ^Bgcj^gGgbb j»c:?oC>"3<^o (WJ* bg6bocj"g(oo ^o^ob b3o(o(8)gio,
igfogooag, Bgb^Bg-gc^jjo bioto^gio. i3^bo)o>G, (O6coogj>coob bogt^iBob bfocoiboo.^G g(ocno>co b3o(o(8)giob ij^ognic.
0O09'>-
<^•^0 ^OObo2>>!» «5^c:oco3gG^g6E;>ij.(ooib, B^ooo 6go»j0oobgGi(ooiGcobi (003^0 HCl<HBr<HI 3o>(8)^c;ocoib, (0^0
Bg^a^b bodc;>og(oob.i G"ggc:;>gco«goc];>'g(ocobob bt^fio^b "gg^ia^otocogb^.
jcnco(o^g.>Cjjio>co3g6g.> cooo^bob (8)o3ig<o.i^g(o^bg J>co30c;)6c? (og-^ao^ogib Bboocorojo Bgb^Bg-gc;) b3o(^5gio)J>G,
3gco(^>g'gc:,o joj* 3o(oggc;>JEoo b3o(o(8)giob ^gBoobgga^^o go b,i^o(oco.> gi(8)J>Eoo*b6^oo(^ob (m-goooob jcocofooj^o)
3^3n3g6gi.i ,iG b6(og.>j0ooo 6j>foggob 3<>2i3(og5^ Jgocoto^giCniiiCooa).

140
 g<<io)i^n3o.i6o "biot^^gioli .iG.ijinn^o'gtn.iCo, Joj:o(^r)^ocooli ^00352?*^ J^cnnggGo'U
^^o8g6oo) l5o(^QogE;>cogi6 o8.>3g ^og-iggB^giocn, ^.^b-gt^gioli 3ot^r)ig63o:

H0(CH2)30H + HBr(i) H0(CH2)jBr Br(CHj),Br

HOCHjCHjOH + HCl(i) .„o > HGCHjCHjCI _„q' > ClCHjCHjCI

gcno3oGo(«)gaol> («>gijJoogio. 8n6g<oj>c?'3(^o .iG 9g'^30i^>^ or).>66coiol>6b lj3o<o(8)3&o'b a«>0bgc::>gaoa)
^03^8nc:;>g3'3C:;>'g(no cogiojofo^^j^QOoli (P-gc:;>o8oGo(^giolj) ^gfiog^^co 8oocogi6. Ggnt^g-gcoo ^6 8g'b.i8g'35::;>o
"b^ofo^giolj 3g8a)b3g30>^o ^gc^ob 3^8r)gn^o> bjogij* bv>oQ33olj ^gbocn: 3^^(»)(8)c^6nb 8nbc;o3B6 bn^Qogc^JoO^'^'
dotooa)6co,ijio, g3gc;?«ib3 S^jc^giico JocofonggGobgi'gsjijo P-Gib^ofoi-Sfioob .>^(*)8oioiG. bbg.^ boj^gggioo,
0(^8^30 i8^ ^6(^800jSGgii g30C?*^*'^0 ^'^^•^O3C?0^'3S2? Gi>b'9ofoi.ic°>>^<*>9f>«^6:
H OH

CHjCHjCH—CHCH, ' CH3CHjCH=CHCHj + HjO

joAgjjcjjijjoo b3ort(8)jjiolj bcn^QOgcjloQiii liijSjcH® bolj(8j 3o(oniQi3o (170-200 C, jwGq.

H,SO,):
CH3CH2OH » CH2=CH2 + HjO
.i8.ibo)>i6, ^.ifG8nojSGgiii, •^a<^0C"30» o)«^6^'2(^o dfonfo-g^j^gio.
8gco(og'2cno b3o(^^giob 8o8j!oo6iit'Sgr)ib 100-150®C ^g83g<o^^iD<oi'bg, G^gcjogiifw gnGQgG-
^fnofngi-gcoo 8^.i3gioor):

Qfa)»H,SO..I30°C 0 ^
joro'vj -yg(^o ticogocjj^ Bojoob SgbiSg'jjcjo b3oA(5)J)bob (;og2oco(^.ij^6QOi (80-100 C, HjSO^);
CH3 CH,
CH3—C—CH2CH3
I
H2S0^90°C^ (CH3)2C=CHCH3 + CH2=C—CHjCHj
-HjU
OH
dDc^oDcogiob {ogJocof^i^^QOobib, dot^nigiob^ joi 3oco<or);jboc>ob jea-g^goiob •g(no)og<na)3iGc;>63gaob
3obgj53oa), bb3^C06bb3i 3(onco"3^(8)gbo 8oocogi6. goQoG^c^-a^o sooncjgiob ai0bgc:;>gboa), 3iGb.>3gi-3SC;>o 83i3gbob
.iG cn-jjoooob jco(*)(^ocoob <n.i6^nbob.ib, 3.>(nicnGocj>'3(^o G.ig(^cr)gbo 8oocogb6 ((ngiijyoob ^"3«iCi;jgi®"3<^o ^^nnjo-g^^gio
g6coc;)gio^):
ZnCl.j f *1
CH,OH "CH^OH [CH^- CHOH] -CH3-CHO
gtijl^o-^Gob iob'j]c;ooj.i(8)a)ii6 ^^b-jutogiobib bjogi^ aJSJOQg^njsijob c50'^"Cs^'^(S)'^O'^'^ ^.i<o8r>o^86gi^ 9330'^^"»
•i<'>Ab6bo^8o36r> b-gGob 8^Gg "gj^gt^o .ic;>cog3o{oo —^gt^cojsjgoGo, <^r)8gcoo(3 ^tnoboi^Ggib a)3.>c|7ob.i co6 b-ib-gGojo
gbgiob confo^ngiiG ^^(obgib:
t®
CH^OH - CHOH -CH2OH [cH2=C=CHOH] CH^^CH-CHO

-j^Gag^, 8^66363giob (KMnO^, KjCr^O^) 8r)j8giogaoa) biot^^gbo o^^Gagb^, 3o(^33c:>icoo - ic:>cog3otogi^co,

8gn<og-3C:oo 30 - gg^oGgb^co:
<^0
SCHa-CHjOH + KjCrjO; + 4H,S0, + K2SO4 + CrjCSO^), + THjO
H

3CH3-CHOH-CH3 + 2KMn04 —^aCHj-CO-CH, +2Mn02 +2K0H +2H2O

141
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coo>o^o>6aQi^.
agli^Sg^Coo lj^o(^(8)Qao 8co3fo6Eoo.i doS^^m fos (8)'35g ^<^>3^0,(^00)6(3 ^gli^tJscjgigcTjoA
860)o 3680)66336 30633CJ6C00 C06 agn^g^jci^o l)3o6(8)3aol»6366. 8^636 663^0 83tj683'3c::>o l>3o6(8)o a66o(3cool)
(03Joco66^6(306l) 60^33601) ^663coj86ooD, 6n83c;)0(j BgacognS^o o36633i6 C-C iaob 3g5r^5oli6
C06 366io)683636l> ^668c)j35oo).
3a663636(« 33o8c:>3a6 3680)303360)0) 363663663i-3c?o li^ocogGdoli 8630)-3c:no(3,6o)83c:;jo(3 jo6<g66'3c:oo6 "3630
o^ojooli <33600). o)'3 6\J30) 8630)'3c;)1j 663-333360) b6o6(8)3o, b^ocjgGdol) Bcn^omj>^n ^3^3636 6c>(D3366, bo)jioo)
"6606(^0 3661:060^36366 6c:ojo33oj:o6co:

R-CHiOH +CuO R-C?2 +Cu +H2O

n

366330b 36o)co-3j536ob 8010366 ^3081^)366 63630)33 6203660)003601) £03301:06063600). 106^(386(336-3200

36562oo%65o)6ob (Cu, Pt, Pd) *b3io63o6'b3 lj3o6(8)36ob o)6o)(]2ool) 36^663601)6!) 200-300''C 53863665-360!)
6060)636^0 bco366 860)o C03J0C0606366;

R-CHjOH ^
R-CHOH-R' ^r_c_r.+h
II ^
o
63 830)o)i:oob -3606650^^^^'^ 3680)3363600) 366bo)6(3032036-32o 830)0)10360)66 ^31:0663600) o86'3o
81:030)86630)61), 6o)8 66 bi:o366 620(03Jo}:o36ob 3381:030)80 <06366336 36660)6836336610.
6o)2ooo)2036ob co<^3-i533ob ^6680)0^86366 636j0oob 66o)io-3^5o>'^ ^66330. 86362000)610,
30)0203632oo30)2oob I5«i3«i6336 6*60)5836360)0 66 ^o)8 (Ill)-ob o)Jboiooo) 6b3 80810066630)61):
CHO COOH COOH

CHjOH CHjOH CHO

CH,OH ac?""d^"c;3a-»3-»
I
CHjOH
CHO COOH COOH
I — I
CHO CHO COOH
ac><w->dl>oc?o 8(2jonjlocj9(|636 33.>363a636

30Q06620-360 I)6o65g6o 03663366, 63630)33, 00)10836360)0. 63 i:o6o)b bio366 C-C 680b ^>>^3335'^
3666(06020-360 6636o)36ob 66 3666o)683636b ^6680)J356:

+HIO,
CHjOH-CH^OH 2HCHO + H2O

-I-2HI0,
CHjOH-CHOH-CHjOH 2HCHO + HCOOH + H^O

G^dJO'GCoo 66680)861533620360. 830)660)200 6063320610 801036-320 0J66 bob "8^66200 368o)biooo)"

-3J6360 bo36033o), b6o(o6660 ^66800^866 8obo b6b32o^o)io366 - bob b3o65o. 3680)0336366
b6^3636io, 368bb632o6(o (5?'^d"b6io36636ob ^6680036630. 8ob366 0103636 <go)6862oio33oiob, 93b6668ob 30)3636b,
b633-36662oo) 663a666536b 156 bbg. 830)60)200 820036 6030)0363666. 5-10 3-ob 660)15360)600)
8oio36ob6b 615680660 6686315366, bo)2oo) 30 3 - b6boj3i502oo)6.
6203660)253601566 a332o«>'b3 (50150 366^5"8"3C5" -^^3^ 30)66o)2ob. 86b, 60)30)60 b6-3330)3bo)
368bb632ob, 03363636 ^080-360 l^668o)36ob bb36i56bb36 15663^0, b683-36662oo) 663a666536ob I56b63'b6i536206i5,
666550-383606^0. 30)6Go)2ob 0(03636 bob 336j6ob 6o(56o)2oo'bob ^gjog^-^io !y663o)J36o2oo aC5'33<o*bob
(5-31502000) (Joi56o)2oo'b-36o b6o65o). 5od^8"3'^ (8066633360b ^3803320) 30)66o)2ob b6^3636(5 b866o)636,
o)(oo)6i5 ^o66blp66 *363336 666b6bo68o)36o) b36ob 8^0)63 33<g36o2o 1566686536b. 6b30) b6o65b io3665'3665b

142
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("bociaob gbgB0ogio'*),{J3,i68g6g6b £06 8<oig,>c:j bbgi Bogmogeogi^b. go).>6oc:j)ob b.ioj-gdggco'bg iBISiiogigB 86.i36c;>o
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(QboBgio) b,iboof). g^gcijn aCJOQgfoncjjo Biijnjbg 3og<^r)bgco3ogc;;>Oii (J-ig^oco^B '3o)^Bo>Jj>gb 40%-8cog
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Bt^g^ggcijobib^ jo^ ^g-^Sob ^it^Bngi^^o. Bobo (oofoo <o,>nEogBr)b.i ob.><02^gbi
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nor)b6(8)CoBo6B b3o('S(8^gib gfoooX^o^gib 9'^o>o g(^cr)-g<oo)o
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I ggg(^(*),^g65;j>^o bbBifioo g(oob{9).icog^o Bo3a»og<ngi5^,<^p)Bgc;ob.>(3 ^bi^bo^ogib ligngoBr)-
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b^B^^^Bcjjogoi.

17.1.2. ?30Bnc?0aO

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Bobgcogocn >><^Rg3gB gf^o-, cn(h- co^ B<oig,3C!Ji(8)r)Bo.>G ggBncogbb.
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OH

(ggBmcon rf)-g(«ig'bmc:jn a-Bogomcoo P-Bdcgoancjo

(^ocofnmjboigG'bncjo) {2-8goDocjo3gBr)cjo) (l-^oiofnmjJboBiXgcndCJoBo) (2-3ncD<'irojJbo6d03cni>cnnBo)

>H

O Q D
3n<'wojO(0)ggn5n 3ofnmjo>Cnncjo
('iQ'brofnyoBo OH
(l,3-o!n3n„«i<ndbnJo6V«,.) (1,2-con3nco('irogboSg6'bmc:jn) (1,2,3-(8)(^o3nco('i(*>gboi35'bmcjf>)
(1,4-(Do3ntDCifngbn5g6'broc?n)

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go'bo3g(«)o <ngoboSobo. ggBr)c;»o co6 Bobo co^i.ic;>o 3c»>Bcoc;)r)ggio Bgggcnfoo toiB^bibo^ojgbgcjo bg6ob,ggg6c»>,
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ggfocn Bijo^c^o (8)gB3g(n6(8)g(^>giob BjoBg 836(^0 Bogmogeogbgio^. o3gBcnc?gio ggfon B^jcogb^jo ^jfnncj^gbo^,
gojofog b3o6(8)gbo, oboBo ^^^BtnjBBo^B gg<nco B^goQg Bncogggcoicjo^oioob ^g^cijb^cogfo bBgbb.
ggBcnc>o 303 ^a^cj^o obbBgb^ ogfo^C?,bcnc:;>(o 68®C ^ga^gCSi^gfoibg 30 - a^Bgb6'bc:)3(#)gc:jo ^nicocogGcnboo).
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b3o<o(8)bi jcocn6r)^r)(^>B^. 3o{D<onjboe>ob S^ggggiob t^OQbgob b^jo^ o^gggb go6t^C?0<^ob
^gico^o bbB^iocobob 8i(8)gb6b, ^bggg gggcnobo^ B^odo bbB^cocob^ bcnciljifogcj ntoa^Bgcj g^BbbBgcjgb^o.
j)o8ogrtoo)3nbo&o2»n- <30^"C?02»" (^cngotoQ d(#>nB6(8)gcno bofotngobpbg ggBncjgfSo 3oco<oco5boc:)ob6a)3ob
143
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^^Bgi^j^ob co(ngcogJ56r)Bo^Bo p-cofoio^icjoo), fonBgcjoQ iot^mgob boi^S^gob
o(^)ogB(9)0(^)ga;3C)o; bjogii p.Tt-^g-gcjCogii jo6 ^6^Bcna^BS;^6 <^)g^gcogj(8)6n6oiBo g(^>o>oi6o Tl-bob^ga.^, focoac^ob
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'3^njogigB),gojo<og igogiBncjo, OT-gdoi oao ao6g(nic:>"3<o joi tofoaiG-gc;^ a^iggboiB ^gcoifogbooD bgg^ifio
£?"^ Sd^'^jG-gbob bbBi(^b gg<ob ifo •jjQgciJob.

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ggayof^gi-ac^joi.
Jocofoco^oc^job 2ia"3'3"^ +M-D'30d6"^ "Oac?0^'^ ^Ar"^ aibiboiogicogio, oao -gojt^n ^ngcijgi,
gofo^og C-0 Mi bboio^gb^ foi, ^gbiiiaobifio dg^oi dobo bod^goQgQ. ido^cod C^-OH Mob a'^^8ao6"®^
dodjooGifng ^ogi^Qogbo ^ggBcocogb'do dig^bg o^goiooi.
g!3do-d-)ig^<«>o wgobgbgbo.
^jrit>j(T,^o(o-ocoGgM)iB ^gjioitogboo) ggBn^oco-ooBob "gg^oco dic;>ij::;oo b^iioj^-gfnnbob g-^^n «ggBo>c;jgiob
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ICqHsOH + 2Na ^ 2C6H50Na +H2
CeHgOH + NaOH ^ CeHgONa + H2O
ijT^gfoaocjai^gbo a^BiJ(^og"gj;[;;>ico bfo'gcjJ'^C? aocot^jofj^obfogii ^gc;;>oa),di3o6 focoQi <gg6nc;)i(^ob Joco^oncjjobob
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3godc;^gbi:
CgHgONa + CO2 + H2O »• CeHgOH + NaHCOg
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coojoo ^gcjocnoi.
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aidooggBgii bbgifoibbgi Bigfocngb^o gi^g^CJ'g'oo ^(^iadgB^ob icodnbiBgBico;

a: +(CH3COO)2Pb —*• 1^^ ^PbJ- +2CH3COOH

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^i6dni(oaoGb, b(^joob gJCjg^(5)^"®c)C? bodggfooggb ifocodi^'gsjj bof^tngdo joi iicogocjgbb gcijg^f^toojocj'gfoo

144
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oogoofoo Giiciogjo ^.)(n3oooj353i.i:
OH OH

+ 3Br, + 3HBr

3b <03.>jQ0.> 3.)i:oiic;>33(n3Broio.i(03.> (3obo bi^^^icogioo) ^godnjogbii 10"'' Scopjjo/c;) gcoB^gG^fo^QOob

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S^bob 'b<0(o^ba)iG gtno^io 8.>o)n bbG.iiot*>ii3 0)6Gcd60)aG 8(30(^cogiA. QTIflo-Mi® obbGgi.^, iS^(^go>gg ,>(^n8i^*2Ci;>o
gi^^inGoco-g^o GigfGo)gio. bigCia)nco,.sjc;>Cog3o5ogbb,j joi J0^)f^5gib ^gjo-if^giotn Co^i^c^o c°'3CJocoob ^g83g<o6{8)"j3<oi
A^gbjgoiofng G.>b^(oi.>co.i(^(*)8a).j 09-^30 ^oQbgob 8^Gg b^o^^gibi CDi gi<^inG8^^ggbb,<^.bQ o8n(n.>^
(Gn8 .icoGo^G-jugn G.igt^(ngi^o ^g6c;ji<>co'3<no b8gioa) 8t»)cngj'jijj»;ni(y)i ^bcoQoiQO^ bjogiii.
jjo3ox3(*in (ngnbgbgbn. ^cjcogJocogiobi jwii 3g^<*>bg5ob joGo-gfoo ogobgigio 6obb6gi.> 8^a)0 8(»)coggii]{;n^giob
OC?OiJd)^"^1DCI?'' •^J^jb.ignioo). g.i<^inGog^ob 3S5'3®3ob 6ib^o<o5^{oob ^0n8o 3<^C?o6(5)'3<^o sp^-Joifoofio-jjcoo
ot^io^Bjig^gioor) ^.i(^8nj36ob bi8 0'-i8,ib (googjjgGob 8b3.S3b^) g6cr> boi<0(8)gg^o, 120°-o^Go g-jgoboo). ^86gg
j:o(^nb,G^b^o(oiiCoob.i go.5 ^^Ggbi^goob 6^n8gib 3n<oob cy-i8giob boi<^{8)gob 86(na)(*)i"2g[n boito^gg^o g<oo)8^Gg0>ob
,i6(n^gT)gjn).2fn^Co 3^Gg;;^.i3gi'j[)gno ^(^^Joifnogo-ggioo p-n(oio(8).bc;>giob 33g<''>CO'3C;jo ^^Co^ojifGgoo) 8g^<ncogii 9o(^<^0 ~
7I-i8i, (oco8ggj;>OQ ^(^bgio(n.ifo ^tiGbbg^gc^Qb^ gcnocjgGob 9cnc;>gg"2g;;)^?o G-sbSo^i^go^^cnSgib ?p>(nob .i^^bgi-ggoo
7C-i8ob6g6G. ^8 '9g8a)bggg63o i8ob 3c^gj^<^<*>G"3g:;>o cj^^'gigcijo g^(^ico6ognob ji^'g^ob G6b3o(oi.i(O60r)8ocoiiG
g.igo^^g-gg^o.i -gogt^co gjjjjgj^t'ico'gtit^gnigoOTo ^iGgbiigoob .i^n8ob^ggG, (^ob 3^800(3 gb '33<>6,>bgGgg;i>o G.i^og];>coi<oog
"jg^tngnigoa) 8^b^b ogigib. i86gg gofoob G6b^o<^i.ij:o,>^c*>8o,ggog^^6r)G'3g;^o gofo'jgigvjob ^-ibgi^coobggG 3-M5'>^g3ob
3^80,Gi^og;;)nbfoog go-ig^gioOTigo o8^b^gii.

R-C^
5+^^" R^S+/>f
^C=0^
5_
H R
C=0 2)8ob gGg^goA (708 33i/9cog:jo) 8g(8)o.i, gogotng C=C 680b gGg(ngo6 (620 33c/8ng]jo), btog^co 8obn
bogfodg (0,121 G8) Gotggngio^ C=C i8ob bog(^dg*bg (0,134 G8). gifninGogcijob jig-gogob 3ng;jo><^ob.i(3o,i "^303^
8(*)g*>ggig{ro^3o (^cogcnt^Q b'^ggjjgcxgog^'jg^^o (G6^og^co&(^ogo go^gogiotno 8'jgb^ob 8^nGg Gib3o<oi.igo,i^(*>8o), obg
0CI?0d(2)'^"*8"C? "jg^fogngoOTo dgb^ob 8JnGg ^.iGgi.igo,i(8)(»)8o) ^g^ggob Qgb^t^giob ,>(obgicoi.>b.
g6'jg66^ogj>gigg;;>o gc;!jgj^^^t*>G"j)g;;>o ^ggog^job 8^oiGg ^iGgiiigo6^r)8o <g"jgdo^Gniob Qg6^(oo.i, bng;;>co g6(^ico6og;;job
5(;g-3«3ob -I-g«ggj(8)0 a-CH d^^g-^tno 0gG(8)(^ob ^i<o8roj3Gib o^gggb. id^btn^Gigg, -gj^gfo ^G ^<on86(8)-3cn
Gj>b^o<o^gig:oii{0'2(o fMJjgoogigiugi'bg 3godg:;)gi.i gJ»Gbco<o0ogg:|)gogb gc:::>g^(§)(nn«gog]j'36n J.6 6'3gg::>gno30g:;>g(no ^g(8)ggi.
3<^30C!?o3g bg8cn>ic;>Go?G'jgg;;>o g.i(^icoGog;;>'jg(no Giigfocngiob diigoigjj (ogii^Qoob'jgG.ifooiiGnbi^b gisG63o(^c»)ig2>b.
n-«y'gdoi)6(»)<Sob (3365(^0

aci.'Ot)0'^"'3"K?'a<^" C3a^6<^"
a-CH-aa,^g-g(<>o 03^6'*'

^iGggob ('igAjj^ogbo. (n-g boGgj-X^^^o 30^^obg;;>ob n^bogoob •idoiig'jgfo bbG.i(ob <ig:;>gog3ogob c»<>g"38.i(^g6a) goi
Go><oggb g«>g6Qbggog<!KX),^g:;)gog3ogoo o^^Gggb^ G,>b3o(^b.>goi^ci8giob ogogg fooQbgob ^gd^ggg]^ g.>(^bnG8;gig.igo,b(*)g:;»n
30^O^C?^ g"^9nogng^gii boGg^-X^ob 33C°C^3^'bg b^C^gob b.iboa) (gg<^Qbg;;>ob b^t^gob (^g.ijQOi):

R-Ct°H + 2[Ag(NH3)2]OH Un
^^9 + 4NH3+HjO
6G6g;jr)go"jg(^6go 8o8goo6.it^g(nbb <ic;!jt®g3ogogbob g<iGgg.> b3og^gGd(II)-nb Jogotncojbogooo). ^8 '3g"i5iibg6gg;oob
.jbg^^godogogi-gg;^ Qob<gg<o G.>g;;>g^'bg ^gjjgogJogoob bbG^t^ob i:o,i8^^gboa) go,i Gi(^ggob 3'i(3bgg;ogboa) gsg<o
^^(n8noj36gb^ b3ogi>gGd(I)-ob Jogot^n^ogoob ggocnggoo 6.ig:;>gjo, (^»n8gg:;>oQ 86g];>g ^ocn^o <gg<nob b3ogi)g6d(I)-
ob njbogoigo g,>(ogo6oJ8Ggb.i:

R-Ct° +2Cu(OH)2 »-R-ct°^+ 2CuOH|+ H,0

2CuOH + H2O

^iGggob co<^ogg <^g<>j0O6 ^godg;;)gb6 g^SngoggGno) .3g;;>gDginj:ogiob ^godnb^BgG^go.

,>g^gog3ogogbob (ngobgbooDO giGbibgjgfoobiogob oggGgbgG, ^g^gtngg, (ogijyo^b g-gjboGgcogot^gocogiGdaj^g^bOT^G.
(n-g ^-gjboGob (b^igngiifno) ^otnggno «J3g<^ob bbG^(o'3o jig6(8)6(^>gio) gco^ot^goog^G io<ob, bbG^^oob 3g<gg(^>og:onbi
j(ngb^ <g"2jboGgr)go(ngo(*)g6G8^6gob ^6<o8nj36ob g^8r). 8og!>gb"jgg;j bbG.><G*bg .ig^gogiogoob go.i8.>(8)gbob^b go
gr)aoeoj5(IV)-ob cojbogoob dngogg-agijgbo dn^ggogii •g-gjboGob 8ng:ogg7)g:;>gib go^ bb6^(^)ob ^go3g(^og:ona^
149
 ^jljo6aa)ao<^c»c«)3i63^63^ 36803033600) icjcooiojoQaolj 6E:)8oaBo6 (^36^5036(0.
go6a6co^33ojool) ^653301)61) 3^36 ^ifoaoojaSjjii ^066^33^)83636,(^)033100(3 ^38(033036633^6 661530(^836368(03,
0^ 8^ o3(0356 ^3(06(0 (o.^ 66b3o(^i6(o(IV)-olj oJUocoijo:
H-C^° +2[Ag(NH,)J0H • H-C^° +2Ag+4NH,+H,0
V pj ^ UH

H- + 2[Ag(NH,),]0H —»- CO^ + 2Ag + 4NH, + 2HjO

^OH

33^0632)0 6(^6o^'3joo (^3633653^00) 6(^ 036633^6. o1jo6o 8l5ojoD(o 836(3(^) 8o(^oi3b'3o 3660(3(0066 366336!)
8(003(00 83663633^00). 686bo)66,b(03i,) C-C 2)8ob 36^333^6 co6 b6^3ob 335060)1)6 33(o.)(o3ioo) 66b^o(^)2)6(oi5o83iol)
^(00 8(30(^3 (#)0(3b3ob ^38033(00 366330b 8(^o(o'g^53iob (do(^)oo)6(oi(;o, 3.)(tf»io683633iob) ^6(080^866:

^ H^R' -^R-c-oh
R-c-cC^„ [°1 „ -<.0 + R'-c-R"
i?
8oo(«)0)obob («)36(J(303bn. C=0 36(^)io6o(oob 2C37)«g3o 7t-i86 8(003(00 8o(06(oob6(3oob 3680 6(030(oj>co
^3(03^6 H®^-X®"5o3ob 8o(o.)(#)'3(;foo 8o(033'3(03bob 'b38o^83(53bob ^3(0336(0. ^036(06(0,3b 8(oo03bo ^sodjojjii
^38(0330 bj38oo) 363oob6bob:

8+^0^8+ 8- ^OH
R-C; +H-X »-R-C
1
I
1
I^H
X

8o3(^o)3iob (^36^(306, (0030(^(3 ^3bo, 36(')io6o(o'j»)(oo 66b^o(^i6(oob 6508^3 6'33(03o<go(0'3(oo 66^o(o,)3ob

•9353300) 0^3366. 6b30)0 66^o(o,)3ob (oo(ob 6b(^'3(03ib 80^83(00 (^363365ob 660060 (oo6'3(oo 663(oo)ob
333o)b3336'9o) 66 68 (^363365ob 33(0336o(ooi6^o ^38636(00 65080)6 3^3*3030 o)63ob"3g6(oo 3(03^(^o6i»)(oo
^330(oob 8J063 (008350083 (86365000)6(0, ^.)63&6(oob, 6bo5ob, 3030(o(oob (©,> ,).^.) 6i>)3(03co«go(0"3(^o
61)^050^30 "3503^ 36(oio6o5oob 2(;3*3<gob 66^0(000^(^030 (o,)(03boo)o 8^b5ob 8^063 66b^(obi)(o.)5o8b (o,)
•33(oo)(03i6 8.)b, bo(oco 7i-i8ob 3(!;;j3j5^^^"3C?o ^663i6(Dob 65o8ob6j36 36(o,)6603(O3iob ^35033650 3b
•3j666b363(oo 6(030(o,)(;o o3(^o)3bb 36o5f^6b.
(o.)(oo36(oob +I-3<g3j5"^ 3680 335"^0^^> 6(0503Jo(03io)66 ^3(oj>(Si3<!>oo), 36(^2>o6o(oob 3^3'303ob
6.)b^o(oi6(o65o3b3 66^0500^(^030 (o,)(03boo)o 3^b5o "ggtoo 8(^0(036 (oi 8o3(oo)3iob (^36^303^0(3 '3<g(no 863(o,)5o
^6(^086(00)3^6.
86^6b,)(o.)83,.)(o(03Jo(03iob6 (o.) 335o632)ob6o)3ob (Oi36b6bo60)3b3(oo6 6'33(03ogo5o-2(oo 8o3(oo)3iob (O36^303io
(o.) 3b (')36j303io '3<g(oo 6(0305o,)(o ^i(^o86(^o)3i6 650(03Jo(03i'9o.
6) 0O66636(o&6(gdg636b 8o3(f)o)o&6. 6(o(D3Jo(032>o (o.) 335<^53bo 33(oob 6'33(03<o<go(o"2(^)o 3o3(^o)3bob
3066^g6(oi,)(!o8^636bo)65 33b6b68obo 30663o(o(^o63iob (a-3o(o(#>o^o6o5(^o(03bob) ^6(^80^600):
H^OH R.^ ^OH
R-CC +HCN *• R-CC ^C=0 +HCN ^cC
H CN R R CN

b) 665(<o^8ob 3o5oi<ob^£OQn5ob8oQ(^o)ob6.6(o{03Jo(03io (o^ R—CO—CHj 50^0^

665(^o'g8ob 3o(o(^ob'3(o<go5o)66 3(oob56(o'3(oo 6o30)03(^3b3bob, 3.^. Jo(o(oob*2(oojo5'3<oo 66^6rt83bob
^6(080J36oo):

R-Ct° ^NaHSO, • ^;^::c=0 ^NaHSO, -cS,'^-°sO,Na

6co5o'35'35oo (^31)^306 (O,)3ib6bo6o)3i3(oo6 36(^io6o(o"3(^o 663(oo)3bob6o)3ob (o.) 3680033633^ 86o)o 368o3o«gob6
(06 36b'3go)6333ob6o)3ob, (^650366 3oco(oob'3(o<go5"3(^o 66^6(08330 bo(oob bb66(^ob 80^83(03300) 6(030506(0
0^50336 o)63ob'2<g65oo 650(o3Jo(oob6 (06 335'*>^f'^ 363o3o<goo).

150
 a) "gt^OTogfoojSgjogi'U ^g^cjo^G ^gliiiiiSolio JocD^^^^2ioli ^6(^8ro^35oo>:
^O H^OH
R-CC^ +H0H:5=t R-Cvq^
aocogi-gjn, 1j3o(^^'3o gfoo) 6^b'9o<^5,>coo'b i(8)e)8o)66 n(no JotDt^cnJbogno'b 2Ca'3^"'^
(^n^ntoQ QGnioc;>o.i, .ibgoo £ooc»)c;>gio ,i(^i3cog<o6too6. ii3o^(*)3 (ngi^QOi SSOC?*^
ojcot^iS^CijCogJotoo'b (^a^^Qoob ^n6ib^n6nii 36(<>0b6ogo>^ go>coib<^)ocoo. «gr)fG3.ic:oiogiocoo jo, (nr)3j[:;>ob
Gj»b^o<^i.iC06^m3'bg Ijo3gg(^ogolj c^ggoQO^o bigSjiDco coocooo>, ^g.Nc:;)bb66(<i'9o b'^co^gco ^bgo)o
ioco<^i^'3C;jo gr)<G3oa) ^(obgicoib. ^gic^ijbbGifogi'So gg^coGgiob 3ofD<o^^.i0O6 bjogb^.
{o) b3n(<|8)Qbnb 8ng(«)(nQ&6. ^cjcogiocogbo (3g(8)Ci6gio) •3<Go)og6oDj3gcogib b^ot^^gioD^vG (o<> ^,i<G3(»>J3Gob
Gibgg^<G6(3g(8)6c;>gib (Gibgg^^gg^^cogftb) iG (306"^c:?0^^) "
\ +R"OH,
^C=0+R"0H -; ^ + H^O
(R')H (R')H OR" (R')H OR"
or)"2 Giigfocnob 3njj;>gg'3C^i>^o gfoOTpofoco-gcnibCo .igjjjcogiocoob (iG jg^cnGob) JCSID'S^O'^'^ iocofonJIjocnob
2^a-g<go0, 3j>'9oG 3gb.b3c:;)g6gj::;30^ 3j»(no '9oaJ>3foc:;>gg'gc;j'3(no ^g^OTogtGoojGgcogi^ £»<> Gj>bg3.i(G60g(8)Oc:;>ob
(jG 66bggj.<G3g(8)iCnob) ^,i<^3nj36^. ^OyGb^g'gcnf^gJoor) b^o>ioE;>"3tGo^ b-goD- coj> 0"3C:?'3^"
6^bg3^6^Qg(8)6Cogio (^6 G.ibg3^63g(8)^cngao):
^O
H0CH,-CH,-CH-CH2-C'^ CH-CH^-CH^CH^-CHOHCR)
--"«> l o '
g) 3oco(*>o(«igbA. «ic;jcog3ocogio joi 3.ic;>iiji;;> (5)o9'^0^'^^"3^'^"'^0 OiiGiniob^b
og(^>a)gib ^gj»c>i^{ob ^^(«i3n^3Gob .is^jg^Gcocijgib. iS^bm^G, 3ootngai 3ofG3gc:>6Coo
b3o<o(8jo, bngon 3g(8)C^Gob ij^co^gGocn —Ggofng-gcijo b3o(^^o:
^O R^ R'
^ r-ch^oh ^:;c=0 +H2—^
3) jnGcogGb60onb <<>3Aij0ooSo. g^fobcoGoco-gfoo 2ia'3'3<^^ -M-0'30d60^"^ 9o'fc<^^OC?
Gib^o<^i6j^.i5o3bg oj3Ggio gc::?gJ5<^o6'3c:oo bo333(^o3ob i5a«go0o(8)o,eo^0,(n63ob 3b(^o3,36b(n^G io^3^3?o(ngb'3c::>o
^a^C^a^jDob 6(8)(n3ob 33(^^cocoaib a^G^aotocoigab. gb ^gicoa^coi^oGo 5'360 *^^3^" ^c::>c»o3ocoob (^6 3g(8)n6ob)
9«^C?03'3C?«^^ 3(nco(8)nGob b^botn.bDCoco co6(tf)BgGocno 3A6a6Gor>Go,6r)3r)fG0 G-ggcognojocoo,"ggig^f^jogb^
ijnrjjogJojoob 3gfo(Gg Gncj^gg'gj^ob gif^anGojuioob Gib^o<oa.iCo,i^r>3b. btoga^ .>b.ic]jo C—C a3ob
^^(^3(«>j3Gi,G^b^o(^a.>jo6(8)r)3cni 2i-i^3ob biojoi 3gcoi6gaoo) fnm-gcno 3r)c>gg-3c::>^ Goo^jga^. ^bgo) f^g^j0og<!>b
3coG£ogGb^0oob <^g<>j0ogib "g^nj^gigS- a^Ggoboj^jjno) oboGo <>0g{8).ic;>cog3ocoob G-ig^c^ooibg.
<ogo.d0oob aot^ggc^ O^'^'^'ba ^^fGGcoo^Gga^ ^Cojonj^o (^C?C°0'^"C?'^C?3'^'^^S::?")' ^>><^9000^3^
b^bgdJ^cojoga^ — Gogt^oDga^;

CH,-Ct° +CH2-Ct° • CH3-9H-CH2-Ct°

(3-3oco<Gn^oa*3(8)^6.>djo)

9ocjo^'3C!Jo <ic?3oc?'^c? Goodg^"^ *33^0^^ 6djj®g3ocoo:

CH3-CH-CH2-Ct° —-^CH3-CH=CH--Ct°
OH
3(Gr>(^nGob
(a-3(8>gG-2-.id?o)
3P)GdgGb^0oob o3 ^oS\i -^^cnfo^^S. 3g(8)nGgaob ^g9a)b3g36^o 3nGcog6bi0oob 6gi^0ogao
3^0odjgioo) (^o)'3d?'^co 3o3(»oG6<Ggc7ab. br)<o0ogdjC53^'> 0f*>0b«id? cotG^^GobGga^o
Go3a)og(^ga,i(n^ 03C!Job 3t^(»)0gb3o.

151
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•3(^o)O3(^(T)5^3C03ili 68063^0)66, Joj:o<np>5boc;)68o6or)66, Joio<!)6*bo6o)6G, g36ocoioco(^6*bo6o>66 £06 I)38o366i6'bo£oo>66,
^3li6a68ol)6£o,08063^0!) (^ogoli «g'3833ao,I),<o51)o83aoli (II), Joj:o(^6'b(o63aol> (III),o336oc:;)3o£o(S)6'b(o63aoli (IV) co6
11380j6(oi6'bco63ioli (V) ^6(^3co535oo):

s
IV \
/ C=N-R"
/

c = o

C=N-OH
III C=N-NH, /

R' O

C=N-NH-C-NH,
R'

3focnnag(«)o%6(3oob (^go^ongan. 36<^ato6oc|)*3<oo 663(^o>3aoli6o>3oli £0686b6lio6o>3a3coo6, 63<030)33, 3o)coo-

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li^fo-gJj^-jjfooli 363<o(o3n£jo33>2£n73aoli ^6^8co536oor>:

nCH^O •...-CH2-O-CH2-O- ♦ (-CH,-0-)„

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C03(^6CJ>3aoll £D6ll63b6£03aEJ>6C0.
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^H3

SH-C-CC;
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H3C'"h^0'"H^CH
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156
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• [CH2=C - COOH] • CH3 - CO - COOH

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t®, H,SO,
CH,-CO-COOH ' ' » CH,COOH +CO

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II II I II II I II
O O H O O OH O
•

20% 80%

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M H H
801560^60(30690 0^60(3068080

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obbGgii,(303^0 go — o>g<^<30C?oGo i3^q>^gGgab (GognAy ^"gdg.obg Sg-^g-gA cngobgagib (o3oio.>bncjgA ^A.i33gG(8)9o SgSig-scjo
do(nnf:o-j(no C06 aoAoEooG'gjsjo ibm^ob ^(«)(n9giob biAj^bg 9j)A3o^ob S^Aopngab). jocjgb 3^b b-ggoi boboo), doAodicoico, oggGgagG
artroG^C^obgA, bd3og(o g.>(o£ooro(8)dG'gA c®>i C^o'gAgb'gcj (^-iAtodiogG) bii'S'gicjga.ij^. ifoga^A^fSjo gg^ocjoGo (80% oigo^ocjoGo, 20%
30)oc;ig6cw.i3oGo) g^Ag^co obbGgbj <^^(3 cnAg^GobaSo 3obo a.>AgG(8)gAicj'g(oj(o (ggGoiSo) ^ggg-iGob bi9>g^c?g^b odcjggi. 030
gdSdoggGgaii a(o<oGj^cjo co6 g'gcijob ibdSgaobi {o^ aAnGjr)ba.ib3gaob, >>3Ago)gg, o9g3o"g(^o oGb-gcjj^gaob^ joj on^gob ^goGBo bobbcjob
3o3dj(3ggob JAnGog-gcjo •ggdiifoobnaob joAcob.
R o R'
R = R' = R" = CHj g"^go6o
j |l ^ R=H R' =R" =CHj o)gdaAp)3oGo
R' = H R = R" —CHj mgngocjoGo
R"

mgroai^mdoGn (3,7-coo3gof)0{^Jb.>Ga)oGo) coocoo AjrocogGnaoo) ggbgcoga^ gi>g6nclo (1,8%), biojo.>G.>0 ^^ASrogab, Rgg-gcjgaAog, 3obo
docjgai. •>3 ocjgAcjnocob 8(3063 rtiiojogGnaoo) 9go(36gb 8^0(3. (ngna^nSoGo 3^i6g ggSob S'JcoGg 83^60 GogmogAga^i, (3bgc;j ^g^cj^O
(3'gjoofio obb6ga.>. 030 -iGign^grt-gcjo mgobgagaoo) b.jboior)joai«i (doAoc^'gcjo i>bp)(8)ob 6(8)n3ob b^i^jjbg -g^cnogrtd^gcogab S^iggadoG,
bdjnjrj cj'>d(?)o3-C?'»d6'^®"3'^" (8)A"g(B,d3g6oob ^gjogg^jo ^A63dj3Gocjo 3oc»6roJbojniob jcg-g'gob b^rtjjbg - ^-g^ggamjG). dgnogocjoGo
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188
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a.>6B6n.>
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JO.) g.)6d.)^(^ro3&o\> 3coafo3.)(^3roi6l». 3olio b^oAo 0^333^ G.>(G3Po3.>Goob 3(000-3(^00 biobgL —3fo(^<goGo'b31).
^ R= R' = H 3fo(oo3oGo
R = H R' = CHj jcotogoKo
R = R' = CHj cogbjoGo
R = R' = COCHj ^3(^10060

N-CH

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Bcojob bi^oG.>Jt53(53a(o 3(oj33E03iooo 303000(^8336. loocoo tooobgaooo 0^333!) docjb. dgcooooGoao 3ro(^^o, B33-3C03b(<»o3. aJ^aO^O^>>
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agdogocjo cooobo bbgo ocn3<>c;rof>coob 30(^(^00je;oro(#K){03iob Go(^33o).
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a-^a'^oac^jo^'ac?'' £^'6300(8,0300. o3obooo6,3obo «go%o<ocooo3o-3(6o 80053315380 30(301:038000 -303(600 dc5og(6oo, 3015(63 - 3ro(6o3o6obo.

189
 XXI015311. ianonaoisaio. 333Sfl<;3&o. m^nn

21.1.C>a06n8^d30&0

21.1.1. oaoenaa^aoaob jcjobosoa^ooo b(&06ono'bnaofo05

^8o6(nag^3gao BAgtnmoJoi, CSco8ac;)0)i St^CIJOd'aCIJOio at^a)Co(^rv3C:>i{o

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itngo 8bcoc^(ojc ^o) 6n8gc;>o83 n6aiGo*b8'3o a3b3{Dgij>. j>8oGr)8^.i33io iG 3fon(8)n3c:o6*b8.i3o ^.ibliGocjo
Q^cngg-gj^o anc^gg-gcijgiolj b^boo) o»<nbgbnbb, iG g(^o)8iGga)0f)iG 3C^3^Cjg6(9)'3<oo i8gboo)^.i co^3^3^o(^gb"gcno
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(8.ia) 8Dc;»g3*3c:;>i3o nfoogg <g-3Gj(30-3(oo g<no) Gib3o<ni^ioi(^n8flDiG^6 co^j^g^ot^gb-gcujo), (f)nd;y[ncn6
^n(^8*jgc;>.> Tsoa'^C^o b^boo) 6bg aisGcoobibgi^l
H
I
R—C— COOH
I
NH^
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ic:Qo«g65"3(o, 6(^n8^(8)"3Cj '5g60'^^O"8C?"3^ AanGnG^^ggi^co; 8'3b(8)ob aobgcogoof) 30 ^bbg^ggigG Ggo^(^ic;)'3t^
(8nGr)i8oGn8nGn36(^inG8gj>3gbo),<g-38g (coo-iGoGcoanGngifoinGa^^ggio) 83^3^ (anGco^anGnjDog^^ifoGa^j^ggbo)
.^aoGna^^ggib.
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6.3.
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bEogi6 b6^3obo 68oGro8^636b Qogoob 8002033*22:0630 G6(^oo3ob "Sgajoga. coi^3ob6oo3ob oj:!ogG^o^o0o(ogi*221?o6 140-
ajog 6bgo)o 6808008^636, <0008320006368 <o68togGo3g 86oo36Gob O3oo<o8*22!j'^ 800336802006 Qb<o. 21.1-ob
333206 3(^oo^goG3gG"2<oo 6808008^636, 32;jo0oGob 36<0(O6, oo3^o3*2<o6tD 6j(8)0'2<oo6, Sgo063b g<ooo
(6808008^636006 •28<o632ogboob6) 68 oo(^ (0^0020300080, oo<030o8o8o) Jo<o62:o*2<^ 86b^o<^i6co6^oo8b. ^o<^62:ocoiob
3(^000 0g8(8)<oob 8^83 3<oao-3<oooo i-gGgitoogo a-6808008^6366 0ob^3o8o (2-68o8oo-3-83(^363^oo.i<ooo3688^636).
030 6<^b3iooib oo<oo 3668(8)oro83(^ob6 co6 86000 <o60g86(8)ob b6booo:
COOH
COOH

H-j— NH2
H,N- H

CH2SH
CH,SH

D-0ob6ooGo L-0ob63oGo
COOH COOH

CH^SH HSHjC—j—NH, j—i

H

(2R)-2-63o6n-3-8g(^36.i(8j(»)3(^>co3660g636 (2S)-2-63oGro-3-9g<o363(^fo3(^oo3669jj636
(^3gb6i69gi6 D-<goo<^96b) (^3gb6i693i6 L-<gco<o96b)
190
 (3b<«incno 21.1. (3ocjo5ob3g8i{5ao^C[!'*'^^3" ^3n6r»>8-j63o&o

^o(hohocno ^jnGo'QgGgio
liJ>3iilicno.i6o gfnoD6ljoo.i5o pi
T

.>(^.i3nc;>.b6-3c;)o (3oco<^oo<gni"3<^o) .^8o6co8^.iggfto

.iCo.^6o6o Ala CH,-CH-COOH 6,02
' I
NH

3.'>C;>oGo Vai V H..,C^ 5,97

CH-CH-COOH
H..C" I
NH,

II,,
jcoqoqoGo Leu CH-CH,-CH-COOH 5,97
H.,C^ ' I
NH,

o'bncoQOQoBo He ClI.rCH,-CH-CH-COOH
. - I I 6,02
CH.,NII,

8goDooo6oGo Met M CM,--CH,"CII-COOH 5,75

I • I
S-CH, NH,

36nc;ooGo Pro ^cii-ai, 6,10

cil, CII-COOII

ajgGo5[;oik5Q;>.>6oGo Phe CII,-CH-C001I 5,98

* I
NH,

3(^<*)<go>Go Trp W 5,J

CIl,-CH-COOH

^ NH,

3cnc;ij>6'3c;>o (Jojotnngocij'g^o) .33oGn8^6ggbo

acjoQoGo Gly G H-CII-COOH 5,97

I
NH..

"bgfnoGo Ser CH.-CH-COOH 5,68

I • I
OH NH,

or)(^gcoGo6o Thr CH.-CH-CH-COOH 6,53

I I
OH NH,

191
 1 4

qo1>^qo6o Cys CH,-CH-COOH 5,02

I I
SH NH,

i^a^cn%oSo Tyr HO CH.-CH-COOH 5,65

I
NH,

0=C-CH,-CH-C00H
Asn N I I
5,41
NH, NH,

0=C-CH,-CH,-CH-COOH
gjrn^^i8o6o Gin i I
5,65
NH, NH,

co.i9*gb(^'3c^o (33^3>i) o3oGr)3^.^332>o

Asp D HOOC-CH-CH-COOH 2,97
I
NH,

^{^^5^8063^63^ Glu
HOOC-CH-CH,-CH-COOH 3,22
I
NH,

Co^cogiooD^Co C0^3-3b(^'3c;)o (<3-333) .i3oGro3^i33io

C;)o'boGo Lys K CH,-CH,-CH,-CH,-CH-COOH 9,74
I I
NH, NH,

HN.
^fo^oBoGo Arg R 10,76
pC-NH-CH,-CH,-CH-CH-COOH
< 2 ii I
H^N
NH,

Joli(^otooGo His H 7,58

CH,-CH-COOH
I
NH
NH,

Cj)H (^U, (j)H

CH,- O- P=0 CH - O- P =0
I I I I CHj- CH - (CH2)2-CH-C00H
CH-NH, OH CH-NH, OH
I ^ I NH2 OH NH,
COOH COOH

<j3n\j3n\jg(no6o ojolngnOTt^gnGoGo Jocot^roJbocjo'boGo

HO. I
CH,-(CH,),-CH-COOH
I 2 23 j
COOH
HO CH,-CH-COOH
NHCH, NH,
I
NH,
H
e-N-Sgajoj^jcjoboGo Jo{o(#>o^o itGnjJijoGo S.S-cooonco^ot^n'boGo

192
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H- •NR H,N. -H H- -NR H^N- •H

HO •H H -OH H •OH HO- -H

CH, OR CR CH3

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bbgi).
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D-OT^goBoBo - (2R,3S)-2-^aoBr>-3-JojB<onjboi'35iBa^^3i,L-(n<o3coBoBo - (2S,3R)-2-^8oBr)-3-ioco(^)r)5boi"3(8)6B-
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3-JojofocoJboi'g^iBa^.ig.i.
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bc^ao 8i(#)2i3Bo38i(^-gBi3oi (Ala, He, Glu jo^ bb3.),bp>3o go - 8^<oobBo38bA-gB63o (Ser, Phe, Trp bbg.).
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(obogj^ojooB, 800) 3(o6ob 6j:o68o6Bob co636Bob8oio6B60
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2R-CH-COOH + Cu(OH),
R-CH-NH, ^ o-CO
, ^ -2Hfi
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^
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I ^-NH.Cl
R-CH-COOCH,^
I I -iNti,L.i I
NHj NHjXr NHj
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194
 H,N-CH-COOH + HCl ^ (H3N-CH-COOH)Cl-
I I
R R

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R-CH-COOH + (R'C0)20 R-CH-COOH + R'-COOH
NHj NHCOR'

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R-CH-COOH +R'CHO i- R-CH-COOH + H^O
NHj N=CH-R'

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R-CH-COOH + HCHO i- R-CH-COOH
I I
NH, NH-CHjOH

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O
II

HN^ ^CH-R
2R-CH-C00H I I + 2H2O

&
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Qogs^n-gioo ^3ocog8o, cjdJ^iagbo:
R-CH-CH,-COOH —^ R-CH=CH-COOH
I -NH3
NH2

^CH^- CHj
R-CH-CH,-CHj-COOH R-CH ^O
I -H2O ^nh-^
NH2
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HOOC-CH,-CH,-CH-COOH -—^ HOOC-CH2-CH2-CH2NH2
I -CO2
NH,

195
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NH, OH
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' I -NH3
NH,

C?) ^1^6330010 coQ'b68n6nfnQbd

[O]
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R-CH-COOH + HNO, R-CH-COOH + N,+H,0
I I
NH^ OH
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HOOC-CH^-CH-COOH + HOOC-CH^-CH^-C-COOH
NH2 o
HOOC-CH,-C-COOH + HOOC-CH,-CH,-CH-COOH
II I
O NHj

196
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b6boo;

+ROH: 33<f>65oo HCl

•--OH -OR
'Hp
OH

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213
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OHHQ ORRQ ORRQ
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H H H H H H
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q' '
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H OH H O-Ac
1,2,3,4,6-3g6(8)AAQg(8)05[;j-D-3Acj>Aj^CT^ot^AGcnbA
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(gnbgA^gio), gb GAgt^cngio "Bgjoob Bgiob8og(^o (jboggc^gfoo joa a^gGAf^ggcj^^ cT(^3AGob8ob "SgcoagGoEJcibABo.
fooicobobA (OA (ogbco^o(<ioiobob gnbgA^gio GggcogoGa^AggiobA (oa gcogg^SgG^giob b^t^-a^gt^'gcoo
0C!J09gG(^gioA. GAb^ot^^gcogiob 8g(8)Aicos:oo'b8o, gn(8)DboGoDg'bo, (oginocoo (oa St^AgAcoo bbgA ionc;)(»)30'a(oo
3<ocoQgbo b<o(^0ogcn(ogiA 3nGcnbA()A(^n(ogiob gcobgA^gbob 8co6A^oE;>gnioo). a3 •agAGAbgGgcoooAgAG ApobAGoBGAgoA
gcoggcobA-l-gcnbgA^o, 3C::!j'33cobA-6-<gcobgA(8)o. (oa g(^'a(j^n"bA-l-6-(oogcobgA^o:
CH2OH CH.OPO3H2
HjOgPOHjC CH2OPO3H2

D^l}/oOPO3H2 OH
OH H
H OH

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8ao)o gcobgo<oocoo(^gi'aj*o 8(ogn8A<ngcobA^ A^bginiob gAGn.
acoGnbA^A^ocogiobAcngob dAgobg SGo^gGgEjtngAGoA (©"iflAGggob <ngA^og6o. dot^cnigiob aobgcogoo) a8 (o^nb
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^gbojCoAgAg^ot^gigCljoA dcocogg'acoA'So GAb^t^iAco-ajjoo JC-^^gob (ogb^6'aJ(30Aba)A6,6go^<^Aco'3(^ (oa 83636 Atng'So
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ojbo{onb AaoAggt^ bbGA(oa)AG ((S^ncogGbob <*>06^(8)030) (oa ^^(8)3 bbGA(^9o Cu^"*'-ob
gp)8dc;>g^gior)AG (ggcjoGgob (^gA^j^ogo) aB Qo^t^A^-onGgioAB (bgGgc^odig^nb (^gAjiStogo):

R - OHO + Ag(NH3)2^ Agi + a-^ggob dt^cojo-a^^gio

R —CHO + ClI^'^(gn83cjgjbo) —^ 0x1,04 + jjAGggob d<o(*)(o'a,'](^gio

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214
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CHO COOH

(CHOH)^ (CHOH)^
CHjOH CH2OH

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'OH
-H^O ho-oh H

COOH

+H2O; H^
OH H
-ROH

H OH

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CHO CH,OH
[HI I
(CHOH), !-!—(CHOH),
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CHO CHjOH CHjOH CHjOH
H- •OH
IH
•OH
10]
H-|-OH H-|-OH
HO- -H HO--H ^•HO-f-H
an/»-ji>n'icyiat>afa H-|-OH
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H- -OH c=o
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CH,0H
COOH
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c=o
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h4-oh
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ch,oh
l-n^-L-a-g-
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HO-HC-CH-OH HC —CH
/ \ // \
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11,14) 3308336386,608 63 3^6066 8o(5337)(563o 20 6663068656(8)080 56 4 068630 8866 Cj-Cg,Cg-Cg,Cu-C|2
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226
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6 CH,-(CHjVC(X)H 3i3^io»G3flA3.>

8 cHj-(c:HjVC00H 6-(oj(>^6do63d ji6<<k)c>8a.>3i

10 CHj-(CHj),-C(X>H G-S»03->G3g63A 3.>6<^G9g.>3,>

12 CHj.(CHj),„-COOH 6-tocic;{),)')63jji3.> C>.>7)(^k>G%>3»

14 CH,-(CHj)„-COOH 6-(5g<^Jt»03A63a.>3i 9o(^)al>g)o68^.)3.)

16 CHj-(CHj)„-COOH 6-33^iCoa34G3ai3i 3o{:;>9o(l)nG8^.>3o

18 CH,-(CHj),^-COOH 6-«j(5,4to33i63gJ3A
20 CH,-(CHj)„-C(X>H G-{)ojn'bjG9^36
22 CH3-(CH,VC00H G-(:^3i«>%.i69g.>3A

24 CHj-(CH,)„-COOH G-(8)3(8>Ai>3w'b663303» i5.oaGr>oQ<^oGafli3J

CH,-(CHj)j-CH=CH-(CH,),-COOH •^£#'«?aOOS"9 (z) 4iEj3ojJncj3oG3^i3A
16
18 CH,-(CHjVCH-CH-(CHjVC(X)H «^d(!i'X50O06-9 (2) -3^030 rTCjgoG0fli3i

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15(z)-3fl63i

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14(z)-3a»3A
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24

227
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0063b 8036663366 863636253606,6636566636 5663653636066 56 63583(^0 5636633066366. 9036663-3250
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00(^025066 - CjgHgjOH 56 8060002506 - CjjHgjOH 6606(8)360. 06033 9603660 3636032536-32506,
806006565,662590^06836366 60-3250 30363606 66600. 00^025662590(8)6^0 —CjjHjjCOOCigHjj ^6680653366
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228
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229
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G^Boogib.
CH3-(CH2),2-CH=CH-CH-CH-CH20H b<goGap)bnGo
OH NH2
O

CH3-(CH2),2-CH=CH-CH-CH-CH2-0-P-0-CH2-CH2N(CH3)3 bojoGjnSogcooGgio
(0g<^68ofD-l-gnb-
OH NHCOR O" ign^tocooGgio)

b«goGgco8ogcooGo SGo^gGgcongiGo (^^ocogGnioo) (^o)b<g(»)gno3o{ogiob b^gfocno foinjwgGniob 4-10%)

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ac? vJ3'^G0'''0^^'^^''C?o (5e?g3(»>*bncj0g(*>68o{5o) bb36 Jboogoc^gi^o "g^gt^co 8g(8)0 (o6(*>Eog6nioo)66.

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Ah cHj
CH.OH
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OH OH
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((?'»t)'>fia"3C?o «|3ciA36)
I I
R R

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g6<ocoij3G.i 106 6. 19.) GcoGi^ocagrobb <gsc:j<>3o6"3<oo 3£*>gg<G3gG^g6ob g(^0)-g<no)o GGo'SgGgjjjngiGo ^.i(^3n3icoggGg5:;9n
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OH OH OH O O

CH,-CH-CH-CH-CH,0-P-0-P-0H,C
^ II
O" O
N

HO OH

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9<ia<^Cl!Joo)b o3 g^ggioo), 6p)3, NADH-ob 9coc;>gg'3co'jij(#)o ^iGgb^cooo), (ocoge)<o0 G^^iGgigoo), 8obo
Co.ijj66ggj>, ^j>A3coj>coagGb dcjogA gabg<^»aP)G«3c:o 6g.ij0oj>b.

246
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6. H. A. TioKaBKHHa, K). H. BayxoB. BHOopranHHecKaH xhmhh. M., "MeflHUHHa", 2005
7. I.flHCHJiKpHCT. Xhmhh rerepouHKJiHHecKHX coeAHnenHH. M. «MHp». 1996

247
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