有机化学课后习题参考答案(汪小兰第四版_清晰版)

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1.1⌕ᐺḄᡂḄᓄᔠᱥᐳᡂḄᓄᔠᱥḄᱥᳮឋ஺ᫀᓄᔠᱥᐳᓄᔠᱥᰚ!"#$%&$'(᩽ឋ$ᑺ$'+ᡈ-᩽ឋ$ᑺ.&"#1.2NaClKBrᔜImol$';<ᡠ>Ḅ$?NaBr@KC1ᔜImol$';<ᡠ>$?AᔲCDE᝞GCH@CCL,ᔜImolLᙠ•OPCHCb@CH3clᔜImolḄLᔠᱥ4AᔲCDETUVEᫀNaClKBrᔜImolNaBr@KC1ᔜImol$';<ᡠ>$?CD஺WTXὅ$?<ᙳTNa+,K+,Br-,C]ᔜImol஺ᵫ'CHCCL,@CHChCH3clᙠ;

1Ha.H-C=C_HᡈHSC!C!Hb.I••c-H-N—Hd.H-3—H••••H-C-CIHHHHi••H“H••:O0HH••i••,iiH-O-Nஹ.iiH-O-P-O-Hh.H-C-C-H••OH-C-H••i••ii••OHHiH0H-C=C-H••II••H-•O•-S-O-HᡈII••so:1.5ᑡᔜᓄᔠᱥmᨵᏔ᩽Etuᐸᔣ஺a.Ib.CHC1c.HBrd.CHC1e.CH3OHf.CH3OCH32223ᫀ:1.6᪷SOḄᵯ¡ឋ¢£,¤0H2sC¥,mᨵ¦(ḄᏔ᩽-Ꮤ᩽§ᵨ¨ᡈjEᫀᵯ¡ឋ0>S,H2஺H2sC¥P1©0ᨵ¦(ḄᏔ᩽§ᵨ@j஺1.7ᑡᑖ<ª«¬ᡂjEᫀd.CH3NH2e.CH3cH20H1.8⏚ᑖTCH3coOH,oAᔲ¯$';ETUVEᫀ¯$';PWT°ᨵC=0±0HX²᩽ឋ³´P᪷CµC¶gᳮP¬$'᩽ឋ;஺

2·¸¹⛳±»2.1ᔁ½¾¿⊤☢Ḅ∑<°ᨵ29mfḄÂÃ|ÄPᑏuᐸᑖ஺C29H602.2ᵨÅÆÇÈÉ(᝞ˬ¯ḄÌPD~ᵨÍÎÇÈÉ)ÇÈᑡᓄᔠᱥPÐᢣu(c)±(d)<ᔜfgḄÒᦪ஺HHHHII—ICH3(CH2)3CH(CH2)3CH3b.CCCCHc.CH3cH2c(CH2cH3)2CH2cH3III-Ô3)2HHHH'IIICICHCH(CHHIC204°r)223HIHI3°CH]CH33CH3CH2CH—CH2-CH-CH-CH3£(CH3)4Cg.CH3cHeH2cH3H3C-C—HCH-CH-CH223C2H5CH3h.(CH)CHCHCHCH(CH)3222252ᫀa.2,4,4ÕÖᵬ³Õ5Õ׳Ø|5—butyl—2,4,4—trimethylnonaneb.Ù|hexanec.3,3Õ¸Ú³Û|3,3—diethylpentaned.3Õᵬ³Õ5ÕÜݳÞ|5—isopropyl—3—methyloctanee.2-ᵬ³Ý|(Ü×|)2—methylpropane(iso-butanc)f.2,2Õ¸ᵬ³Ý|(ßÛ|)2,2—dimethylpropanc(neopentane)g.3Õᵬ³Û|3—methylpentaneh.2Õᵬ³Õ5ÕÚ³à|5—ethyl—2—methylheptanc2.3áᑡᔜz᪀ᐳâ⊤l²ᓄᔠᱥEᵨÅÆÇÈÉÇÈ஺CHCHã*I33a.CH3—CHb.CH3-CH—CH2-CH—CH-CH3c.CH3CH-CH-CH-CH-CH3CH2-CH—CH-CH3CHCHCH3CH333CHCH33CH3ãCH3d.CH3cHeH2cHe/e.CHCH-CH-CHCH-CH£323-C-7HC—CH-CH33CH3CH3ᫀa=b=d=eT2,3,5—Öᵬ³Ù|c=fT2,3,4,5—yᵬ³Ù|2.4ᑏuᑡᔜᓄᔠᱥḄz᪀PᎷ᝞çmÈèéêÅÆÇÈgᑣPìí஺a.3,3Õ¸ᵬ³×|b.2,4Õ¸ᵬ³Õ5ÕÜݳØ|c.2,4,5,5—yᵬ³—4ÕÚ³à|d.3,4Õ¸ᵬ³Õ5ÕÚ³᷾|e.2,2,3—Öᵬ³Û|f.2,3Õ¸ᵬ³Õ2ÕÚ³ï|g.2ÕÜݳÕ4Õᵬ³Ù|h.4—Ú³-5,5-¸ᵬ³Þ|ᫀ

3g.┯PñT2,3,5—Öᵬ³à|ò/h.2.5ᑏuᑖTC7HI6Ḅ|ôḄᔜõÜ᪀PᵨÅÆÇÈÉÇÈPÐᢣu°ᨵÜݳஹÜ׳ஹö׳ᡈ÷׳Ḅᑖ஺heptane2-methylhexane2,2-dimethylpentane2,2,3-trimethylbutane3,3-dimethylpentane3-ethylpentane2.6ᑏuøᔠÕᩩúḄ°6mfḄ|ûḄz᪀

41ஹ°ᨵXmÖÒfgḄ|ô2,3-dimethylbutane2ஹ°ᨵÕmÜݳḄ|ü2-methylpentane3ஹ°ᨵÕmyÒfg±Õm¸ÒfgḄ|ü2,2-dimethylbutane2.7ᵨIUPACýþḄáÉ,ÿ
.ᑡᑖḄ:HCH,Br2.8ᑡᔜᓄᔠᱥ!"#1ஹ%&'(&஺%&*"ᦪ,஺2ஹ-&'3-ᵬ01&஺-&23*"ᦪ45,6஺2.97ᑡᓄᔠᱥᢥ9ᑮ6᣸ᑡ<=⌕?⊤A஺a.3,3BCᵬ0D&b.E%&c.2Bᵬ0%&d.ED&e.2Bᵬ0(&FᫀHc>b>e>a>d2.10ᑏEJ&ஹKJ&ḄBLMNᱥḄO᪀Q஺2.11ᑏ2,2,4—ᵬ0D&STUMVWXYZᑮḄBUMNᱥḄO᪀Q஺

5FᫀH[\FᫀHa]ᐳ3Ḅ2.13ᵨ`aᢗcQd1,2BCLe&ḄfᨵM⊤ឋḄ᪀i஺ᑡjYkḄA,B,C,DᔜM⊤B\᪀iḄᑁY2.14ᢥ᯿ᵬ&UMnᡂUᵬ&pCUe&ḄᔊrstᑏnNUᵬ&u[Uᓄ*Ḅᔊr஺ᶍ2.15ᑖQwC8H*Ḅ&x'Uᙠz᜜ᐝ᯿}VWNᱥḄBUM&~ᨵB\ᑏ&ḄO᪀஺FᫀHᓄᔠᱥw2.167ᑡ0ᢥឋᵫᜧᑮ᣸ᑡ:a.CH3cH2cH2&ICH3b.CH3cH2cH2cH2cH2•c.CH3cH2-CH3CH3FᫀHឋc>a>b

6=⛳px3.1ᵨᑡᓄᔠᱥa.(CHCH2)2C=CHb.CH3cH2cH2CCH2(CH2)2CH332CH2c.CHC=CHCHCHCH323d.(CH)2CHCHCH=C(CH3)232C2H5CH3FᫀHa.2Be0B1BJ2—ethyl—1—buteneb.2B0B1B(2—propyl—1—hexenec.3,5BCᵬ0B3B%3,5—dimethyl—3—heptened.2,5BCᵬ0B2B(2,5—dimethyl—2—hexene3.2ᑏᑡᓄᔠᱥḄO᪀Qᡈ᪀Q᝞ᨵE஺a.2,4BCᵬ0B2BDb.3—Jc.3,3,5Bᵬ0B1B%d.2—e0B1BDe.KJf.3,4BCᵬ0B4BDg.VB3,4BCᵬ0B3B(h.2Bᵬ0B3B0B2BDFᫀH3.3ᑏᑖQC5H10ḄḄᔜ\K᪀ḄO᪀Q᝞ᨵVK᪀ᑏḄ᪀Q,ᵨ஺(E)-pent-2-ene(Z)-pent-2-ene3-methylbut-1-ene2-methylbut-2-ene2-methylbut-1-ene3.4ᵨᑡ¡QḄ¢ᢣᐸḄsp2usp3ᩖᓄ*"஺ᑖḄ஺ᨵf]sp2-sp3Ḅf]sp3-sp3Ḅ

73-ethylhex-3-ene3-e0-3-(ᡂ¦Ḅ*"wsp2ᩖᓄᐸ§wsp3ᩖᓄ஺ᨵ3]sp2-sp3Ḅ3]sp3-sp3Ḅ1]sp2-sp2Ḅ஺3.5ᑏᑡᓄᔠᱥḄ¨ᑏO᪀QFᫀ:aஹ(CH)CHCHOH©bஹ[(CH)CH]CO©cஹ«D©dஹ(CH)2cHeH2cH2cl32232233.67ᑡᓄᔠᱥᑏᡂ¡QAஹ©c>/dஹ».ceஹ3.7ᑏ¬∫Ḅឋ¯°±-9-Cᓝ*Ḅ᪀Q஺(CH)CHஹ/21133.8ᑡᨵஹVK᪀ᑏஹVK᪀Ḅ᪀,஺CH3a.CH3cH2cqeH2cH3b.CH2=C(CI)CH3o.C2H5CH=CHCH2IC2H5d.CHCH=CHCH(CH)e.CHCH=CHCH=CHf.CH3cH=CHCH=CHC2H533232FᫀHc,d,e,fᨵVK᪀

8C.C2H5ஹ/ChyHஹ_/CH)&H3c/CH(CH3)2/HC=Cஹ/JO'/HC2H5H/nஹHH11CH(CH3)2(Z)—1—ỚB2BD(E)—1—ỚB2BD(Z)—4-ᵬ0B2-D(E)—4Bᵬ0B2BDe.H/%C\H/C=C(/C2H5,c=c(/C=C(H/C=CH2/ஹC=CH2/\H3cHHHHH(Z)—1,3BDC(E)—1,3BDC(2Z,4Z)-2,4B%CHHH\/H3\/H3%=C1/H©C=C

9a.CHCHCH=CH¿°4»CH3CH2CH-CH3322OSOOH2b.(CH)C=CHCHߟÁ(CH)C-CHCH3323322Br1).BH3c.CHCHCH=CH-------------------►CH3cH2cH2cH20H3222).H2O2,OH2d.CHCHCH=CH---CHCHCHCHCHC

103.16ᑖQwC5H10ḄᓄᔠᱥA,'1ᑖ·åᵨZᑮC5HI2Ḅᓄᔠᱥ஺Aᙠ⏚ឋçÉ'è⏚éåᵨZᑮBêᨵ4*"Ḅ⏚஺Aëìíᓄî"ïðZᑮÂ\=3Ḅñ஺òóAḄXYO᪀ᵨVWQÜÍ⌕!⊤ôòõär஺FᫀH3.17ᑡᓄᔠᱥᡈᑏḄO᪀QHa.CH3cH(C2H5)CCCH3b.(CH)CC=CC=CC(CH)3333c.2Bᵬ0B1,3,5B(d.e0eöFᫀHa.4—ᵬ0B2B(ö4—methyl_2—hexyneb.2,2,7,7—[ᵬ0B3,5B1Cö2,2,7,7—tetramethyl—3,5—octadiyne3.18ᑏᑖQ÷ᔠC5H8Ḅᡠᨵø5ḄK᪀஺2-methylbuta-1,3-diene3-methylbuta-1,2-diene3-methyibut-1-ynepenta-1,4-diene(£)-penta-1,3-diene(Z)-penta-1,3-dienepent-1-ynepent-2-ynepenta-1,2-diene3.19〉úöw"ᧇᔠᡂᑡᓄᔠᱥHa.CH=CHb.CH3cH3c.CHCHOd.CH=CHCIe.CH3c(Br)2cH32232f.CHCBr=CHBrg.CH3coeH3h.CHCBr=CHi.(CH)CHBr33232FᫀH

11HOCH+H,Undar_H2c=€H%b.HC=CH-Ni/H2CH3CH3catHOCH+H0—"S%,CH3CHOHCI32dHOCH+CH2=CHCIHgSO4BrH3COCHHgr?aCH3C=CH2-1CH-C-CH33IBrG3HCC=CH+BrI32BHOS04g-H3CCCH+H2O------------►CH3COCH3HgSO4cHG-ch.HCC=CH+HBrHgB.3I3H2BrLindlarHCC=CH+HCHCH=CHa(CH)CHBr323232cat3.20ᵨÍᓫᨵ!üýiḄᓄþÏ␺
ᑡᔜᓄᔠᱥ:a.1,41b.1ᙽ2ᯋ2ᵬFᫀ:Br/CCI243.21ᡂᑡ:HCI()a.CH3cH2cH2cCHH*b.CH3cH2cCCH3+KMnO4XCH3cH2cCCH3+HO2HgSO4d.CH=CHCH=CH+CH2=CHCHO22CH3cH2cCHHCNᫀ:

12Cla.CH3cH2cH2cCH.HCI.CH3cH2cH21cH3ClF|ᓝb.CH3cH2OCCH3+KMnO—-~~►CH3cH2coOH+CH3COOH4c.CH3cH2cCCH3+H2OG.CH3cH2cH2coeH3+CH3cH2coeH2cH3HgSO4cHod.CH=CHCH=CH+CH2=CHCHO22[QrCH3cH2cCH+HCNCHCHC=CH322CN3.22ᑖ!CHḄᓄᔠᱥA,#$ᓄ%ᓄ&2-ᵬ஺A()⏚+Ḅ,-./ᵨ61012ᡂᮞ4⁐67஺Aᙠ9:$ᓄ(;/ᵨ&ᑮCH3,HCH2?CH3஺=>?Ḅ@᪀,CH03CᵨDE⌕GH⊤J=KLM஺ᫀNCH3cHeH20cHHC33.23ᑖ!C6H10ḄAOB,ᙳ1QRḄSTᓄU-.V⁐WCX#$ᓄ%ᓄ&ᑮYZḄ[ᱥ஺A\(Tᓄ]^Ḅ,-./ᵨ[2_`⁐67WaBbc2de஺B#fgᓄhijk;lW&ᑮCH3cH0OHCOCOHmnop஺=KAOBḄ@᪀WCᵨDE⌕GH⊤J=KLM஺ᫀNAH3CCH2cH2cHzC=CHBCHCH=CHCH=CHCH333.24ᑏr1,3sO1,4ᑖ(ImolHBrᡈ2moiHBrḄDᡂ[ᱥ஺ᫀNl_lDrCH=CHCH=CHACHCH-CH=CH+CHCH=CHCHBr223232BrCH=CHCH=CHCHCH—CH-CH+CHCH—CH-CH2233322BrBrBrBrCH=CHCHCH=CHḘACH3cH—CH2cH;Cᵯ222BrCH=CHCHCH=CH2HBR>CHCH-CH-CH-CH222323BrBr

13wSxyz4.1ᑏrᑖ{ᔠC5HWḄᡠᨵᾦyḄ᪀mᒹ᪀pC஺HᫀNCHb⛳n=i5IOycyclopentaneb.1ᵬys1—methylcyclobutane1,2ᵬycis—1,2—dimethylcyclopropane1,2ᵬytrans—1,2—dimethyllcyclopropane1,1ᵬy1,1—dimethylcyclopropaneethylcyclopropaneny4.2ᑏrᑖ{ᔠC9HI2Ḅᡠᨵ✏Ḅ᪀C஺1-propylbenzenecumene1-ethyl-2-methyIbenzene1-ethyl-3-methylbenzene1-ethyl-4-methyIbenzene1,2,3-trimethylbenzene1,2,4-trimethylbenzeneᐸᦻ!ஹஹ1-n2.ᵬஹ1•n3■ᵬஹ1.n-4.ᵬஹ1,2,3-

14ᵬஹ1,2,4-ᵬ4.3ᑡᓄᔠᱥᡈᑏr@᪀:SOH30I£4—)2Tᵬ9,2,3ᵬ11eh.1,3ᵬyᫀNa.1,1—Ty1dichlorocycloheptaneb.2,6ᵬ2,6-dimethylnaphthalenec.1ᵬ41,4y1—isopropyl—4—methyl—1,4—cyclohexadiened.ᵬp-isopropyltoluenee.2T⏚2—chlorobenzenesulfbnicacidCH3ICf.HI2-chloro—4—nitrotolueneg.N02CHCH332,3-dimethyl-1-phenyl-1-penteneh.cis-1,3-dimethylcyclopentane¡¢᱐⊡ᐙḄ⚪§——¨©ᦋ«¬W®¯°1-5ec-butyl-1,3-dimethylcyclobutane1-rerr-butyl-3-ethyl-5-isopropylcyclohexane1-±s-1W3-ᵬysW1.ᱯs3•n-5•y4.4ᢣr☢@᪀1-7©UkḄᩖᓄ¶᝱

15427l-((2Z)-3-(cyclohex-3-enyl)-2-methylallyl)benzeneSP2ᩖᓄḄ!1ஹ3ஹ6©WSP3ᩖᓄḄ!2ஹ4ஹ5ஹ7©஺4.5ᦋᑏ!¸¹ᫀN1-methyl-4-(propan-2-஺ylidene)cyclohex-1-ene3-methyl-2-((£)-pent-2-enyl)cyclopent-2-enone(£)-3-ethylhex-2-eneᡈὅ(Z)-3-ethylhex-2-ene

161,7,7-trimethylbicyclo[2.2.1]heptan-2-one(E)-3,7-dimethylocta-2,6-dienal4.6ᑡᓄᔠᱥWᢣrÔÕᨵÖ×᪀,CᑏrãäḄ᪀å஺HCHHCHRA31AA3HC2H5C2H5CH31-ethyl-1-methylcyclopropane2-ethyl-l,l-dimethylcyclopropanec2H5CH31-ethyl-2,2-dimethyl-1-propylcyclopropane(æÕçᨵÖ×᪀m᪀pÝ’CHCH331-ethyl-2-isopropyl-1,2-dimethylcyclopropairᨵzEée᪀åWCXêëឋUk,jᨵàᐝ᪀(RRஹSSஹRS)஺4.7ᡂᑡ:

17CH303Zn—powder,HO2ᫀ:

184.8ᑏr1ᵬ3yO1ᵬ4yḄ\1᫹᪀î஺ᢣrᓰðñḄ᪀î஺ᫀN4.9ᵬḄÖe᪀ᙠòóᐗõö÷Wᔜ12ᡂÖeõö[ᱥøᑏrãäḄ@᪀஺ᫀN4.10ᑡᓄᔠᱥWÔÕ\1ᨵ✏ឋø

19a.b.c.d.ᫀNb,dᨵ✏ឋ4.11ᵨEᓫᓄúûü␺ᑡᔜᓄᔠᱥNa.1,3yW1ᯋb.yᫀN

20ᫀ:¢᱐Cþ⚪(ὁ᱐
:

214.14ᑖC6HKḄA,═⏚ᓄḄᓄ!⁐#ᙠ%&'ᓄ()*+⏚,ᵨ஺A/0ᓄ1234567ᑮ9:ᑖC6H஺2Ḅ;H<=Ḅ>=ᓄᔠᱥ஺ABAḄC᪀ᵨEFGH⌕JK⊤MANOP஺QᫀSᓽUVWXUWYZ[\]<=^_`ḄᑖCGHIOḄᔜ:e᪀fg᝞i[ᔜ:e᪀f஺4.15ᑖC9H12ḄjᝯA,i┶⏚ᓄm7nᐗp⏚஺qArstᓄ67ᑮu:9t`vᱥ஺ABAḄC᪀஺ᵨEFGH⌕JK⊤MANOP஺QᫀS4.16ᑖC6HaBraḄA,iw⏚tᓄ67ᑮ9:9t`vᱥANAḄC᪀஺Qᫀ:A.4.17x_mᑖy7ᑮuzᑖCHClBrḄe᪀fA{B,qA|_7ᑮ}:64ᑖCHCIBrḄvᱥ~B/_7ᑮu:ᑖCHClBrḄvᱥC{D஺632632A_mᡠ7vᱥ9)C#ᨵ9z)D஺ABA,B,C,DḄC᪀ᑏᔜEF஺QᫀS

22ᐝe᪀5.4(ᑡᓄᔠᱥzᨵᐝe᪀f᝞ᨵឋᵨ᪗஺ᢣᨵḄᐝe᪀fḄᦪ஺CH3a.CH3CH2CHCH3b.CHCH=C=CHCHc-33ciOOHIOHefCHCH-CH-COOH.ᔾn3g-OH▢CH3LaQᫀS*CH3a.CH3cH2cHeH32zb.CH3CH=C=CHCH32zc.LO2zCld1…<3HOHy*¡.CHCH-CH-COOH22=4zf3OHCH3CH3|CH3£*2zi.2zj.O¡9-HO^^OH¡h.0¥᱐
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235.5(ᑡᓄᔠᱥzᨵᐝe᪀᪗ឋᑏᨵḄᐝe᪀fḄᢗ¨,ᵨR,S᪗ª«¬®Kᑁ°fᡈ᜜°f஺a.2—_919´⏣b.a,B9n·_´n⏚C.a,P9n¶_´⏚d.29ᵬ`-29´W⏚QᫀSCHOHa.CH—CHCHCH£CH2OHᓝ2H2223H-BrCH2CH3CH2CH3(R)(S)(º00H(S00H(º00Hb.HOOCCH-CH—COOHH——BrH——BrSBr——HBrBrH——BrBr——HH——Br(ºOOH(S00HC20H(meso-)(2S,3S)(2R,3R)(S00H!CS00HCº00HS(S00HH3CCH-CH—COOHc.H——Rr'cuHl_wDrτDr—BrBrH——R1Rr——HDIriτ11DI(SH3º(SOOhT(20HSCH3(21S.3R)(2Fஹ,3Sº(2(3,3S)(2R,3R)d.CHC=CHCOOH3CH()35.6(ᑡᓄᔠᱥzᨵᐝ½ឋ᝞ᨵᢣᐝ¾ᔣAᨵឋ3ᦑ¡B(+)⊤MᑖᨵÁᐝឋCuzឋ3ᑁ°f᦮zᑖÃᐹᨵᐝ½ឋÅ5.7ᑖÆC5H10O2Ḅ⏚ᨵᐝឋᑏÇḄ9ÈÈ᧜fḄᢗ¨ᵨR,S᪗ª«¬஺QᫀSCOOHCOOHH-|~CHC5H10O23HC-^H3CHCHCH2CH323(R)(S)5.8ᑖC6H|2Ḅ>=ÊA,ᨵᐝឋ஺/'ᓄᓄËᡂ¡ᐝឋḄB,ᑖCHOᑏA,BḄC᪀஺614QᫀS

24c6H12n=1ACH2=CHCHCH2cH3BCH3cH2cHeH2cH3CH3CH35.9+9ÎÏÐḄ᪀Ñ᝞(:HOHHCH3Çiᵨ(ᑡzᢗ¨⊤MNHCH3C6H5CH3Ò5n5aH——OHb.H——NHCH3c.HOᓝH-H——NHCH3HO——HCH3NH—CH3NHCH3CHC6H5HH3QᫀSb5.10ᢣ(ᑡᔜÈᓄᔠᱥÓḄÔᐵÖ×Ø:e᪀fᡈÆᑖ஺COOHHCOOHCOOHHC-C-HH3C-C-COOHb.392H5HCH2CH2HCH3H3cஹc2H5CHCH33CH3c.d.HOOC.txOHHஹOHHCOOHCH3CH3H—1—OHHIHH/HCHCHOH32COOHHz~CHOHCHOHh.22H—j—OHHO—HHOOÝ☢ßOᩭᡈᙠÝ☢[ß90°,ᢥ᯿ãᑏᢗ¨äåḄ3ᑣÇçF_⊤èé᪵ḄᑖëÑ)IÆèéᐵÖ

25COOHH-|-OH(I)CH3Qᫀ:COOHìOH(I)H|0||Ý☢[ß90°HOOC—PCH3È᧜e᪀CHH3(R)(S)COOHy>Ý☢ßHO—HÈ᧜e᪀CH3(S)5.12íî⏚ḄC᪀oCOOHIICOOHHN——CH—C——OH2NHCHHC2CHHN33322-aminopropanoicacid(7?)-2-aminopropanoicacid(S)-2-aminopropanoicacidCOOHCOOHNHHN22CHCH335.13ïðÆ╋òóᱥzឋ2,zᐝe᪀f஺codeine

265.14(ᑡC᪀ÆzÆᑁ°fQᫀSa{d

27ôõöᓴ_ø(®úQᫀÆᢥ᯿ὁ᱐
ᦟýãᡠ,ᨵþ⊡ᐙᑁᨵᓄ)6.1ᑏᑡᓄᔠᱥḄ᪀ᡈᵨ஺a.2ᵬ3!b.2,2"ᵬ1Ớ$!c.%&'!d.(")*e.2)1,4+",f.(CH)CHIg.CHCh32h.C1CH2cH2cli.CH=CHCHC1j.CH3cH=CHC122-ᫀ/Bra-CH3CH-CHCH3CH33-)0*f.2—Ớ$!2—iodopropaneg.)1ᡈ2)ᵬ!trichloromethaneorChloroformh.1,2—")0!1,2—dichloroethanei.3)1$,3—chloro_1propenej.11$,1-chloro_1-propene6.2ᑏC5HllBrḄᡠᨵ4᪀56ᵨ6789ஹ;ஹ<ᓴ%>6᝞@ᨵAឋCDE6FGH᪗6Jᑏ(᧜4᪀5ḄᢗM஺2-bromo-2-methylbutane1-bromo-2,2-dimethylpropane

286.3ᑏ")%ḄNOCḄᡠᨵ4᪀56᝞ᨵAឋCDE6FGH᪗6J78PQḄRᐝ4᪀5ḄᦪU஺1,1-dichlorobutane1,2-dichlorobutane1,3-dichlorobutane1,4-dichlorobutane1,2-dichloro-2-methylpropane1,1-dichloro-2-methylpropane6.4ᑏVᑡWXḄY⌕[ᱥ6ᡈ\⌕]ᑺᡈ_ᑺ

29C0HC6H5cH2clߟ2Et2஺H2Ob.CH=CHCHBr+NaOCH2225EtOH.r.tKOH-EtOhjCH=CHCH02-~"C2H50H2஺j.CH=CHCHCICH=CHCHCN2222k-(CH)CI+NaOH.H?°33-ᫀ/a.C6H5cH2cl—__C6H5cH2MgeI.c6H5cH2coOMgCI--H--C6H5cH2coOHEt?஺H2Ob.CH=CHCHBr+NaOCH---------CH=CHCH2OCH2225225d.

30e.f.CH3cH2cH2cH?Br-CH3cH2cH2cHzMgBr02H50Hl`3cH2cH2cH3+BrMgOC2H5g.h.CH=CHCHCIChF»CH=CHCHCN2222(CH)CI+NaOH-H2°->(CH)COH33336.5ᑡᔜ(ᓄᔠᱥᢥSN2ᔊdefWX6gOWXh᳛jkla.(CH)CHIm(CH)CCIb.(CH)CHIm(CH)CHCI32333232d.CH3cHeH2cH2BrmCHCHCHCHBr322CHCH33e.CH3cH2cH2cH2clmCH3cH2cH=CHCI-ᫀ/a.(CH)CHI>(CH)CCIb.(CH)CHI>(CH)CHCI32333232d.CH3cHeH2cH2Br>CHCHCHCHBr322CHCH33e.CH3cH2cH2cH2cl>CH3cH2cH=CHCI

316.6pᑡᓄᔠᱥᢥSN,ᔊdWXḄtឋᵫᜧᑮx᣸ᑡa.(CH)CHBrb.(CH)CIc.(CH)CBr323333-ᫀ/b>c>a6.7ᎷSN2WXQᓄ6ᢣ(a),(b),(c)ᔜ%⊤l-ᫀ/(a)WXtᓄQ(b)WX᝱(c)WX6.8ᑖECHBrḄᓄᔠᱥA,ᵨᜐᳮ6ᑮ¡OᑖECHḄ4᪀5Bm4948C,ᑏA,B,CḄ᪀஺-ᫀ/ACH3cH2cHe£BCH=CHCHCHC.CHCH=CHCH(Z)and(E)22333Br6.9©᪵␺¬ᑡᔜᓄᔠᱥ?6.9ᢣᑡWX¯Ḅ°᪶_ᑺஹ²ᱥஹ³´µᶍ6.10ᑏᵫ(S)-2-º!ᑴᜓ(R)-CH3cH(OCH2CH3)CH2cH3ḄWXᔊdOCH2cH32-bromobutane2-ethoxybutane6.11ᑏ2OPFᵨᩭᑴᜓ3,3-"ᵬ-1-JkḄ"Á%ᛀḄ᪀஺

32Brl,2-dibromo-3,3-dimethylbutane2,2-dibromo-3,3-dimethylbutane6.12Ã2-ᵬ-1-Ä$!mᐸÆÇÈ_ᑺᑴᜓᑡᓄᔠᱥ஺a.4,b.2-ᵬ-2-$☟c.2-ᵬ-2-$!d.2-ᵬ-1,2-"Ì$!e.2■•ᵬ-1-Ì-2-$⏣-ᫀ/CHCHCHBrKOH-EtO,CHC=CHhf3232CH—Îߟ'CHHO332CH2Brd.c.6.13ᑖECHBrḄA,ÏKOH-0Ð]ÑᐳB,ᑖECH,᝞ÓBÏHBr3736Ôᵨ6ᑣᑮAḄ4᪀5C,Ö×AØCḄ᪀6ᵨWX⊤8Ö×d஺-ᫀ/ABrCH,CH2cH3B.CH=CHCHC.CHCHBrCH2333

33Ù£ÚÛÜᑖ᪆1.QÞßḄ2500/cmã7/äᜐᡠåḄQÞæçèå⚣᳛ḄßêëìèíḄᜧx஺îïðḄßêðÏðÞᜧxḄìñ஺ò☢Ḅ⚪UḄõÏäöñ÷2ஹQÞßḄ5øù3ஹ300MHzQÞß4ஹüý5ஹC=O6ஹ᪀3300kḄC—H,3100*&ḄC—Hÿ2100Ḅ;1500-1450Ḅ800-600ḄC—H7ஹ᜜᜜8ஹ9ஹaஹᦪ$%&'ᐳ)*+%ᜧ'ᡠ◤/$%0'1'23%3Bஹᵫ6&789:;ᵯ=ḄN?=@'ABᐳC'1CDDஹᐳF*+%ᜧ'1%G10ஹ240ᜐ"T%*320ᜐ“7O*11ஹPQRᦔT'0U'VW'ᓄYZ1ᜧ12ஹ[U\ᓄYZ1ᦪ]^_Ḅ7`abḄcWda.BrᨬhḄHbஹᓫklCஹmnḄHDஹoᝯḄHEஹrsḄH13ஹt/'uvwᨵyz{='|}~ᑖ஺஺14ஹaஹz'CH3ᑖ3஺CH2ᑖ஺OHtᑖ15ஹᶍBr/\16>a^H2c—Br7z'121CI/CI-------HCBஹV஺7ci-"z'7z'yzḄ12……ᶍ17ஹB18ஹba1d;Tf᪀a2d-da3d-a19ஹ20ஹᶍ21ஹBrBr22ஹ

34⏣8.1¡¢£ᑡᓄᔠᱥH3CJCH2cH20HXa.b.CH3CHCH2OHCF'H-Ch2cH2-QHCH2cH3BrOHOHd.C6H5cHeH2cHe§CH30cH2cH20cH3g-5CHOH■"OH3h.¨ᫀa.(3Z)—3—ªo⏣(3Z)—3—penten—1—olb.27«r⏣2—bromopropanolc.2,57¬⏣2,5—hcptanediold.47727ª⏣4—phenyl—2—pentanole.(1R,2R)—27ᵬm⏣(1R,2R)—2—methylcyclohexanolf.v⏣ᵬethanediol_1,2—dimethyletherg.(S)—®rn(S)—1,2—epoxypropaneh.°ᵬm-methylphenoli.17v⏣1—phenylethanolj.47±71ߟⅉ4-nitro-1-naphthol8.2ᑏᑖ=µᔠC5H120Ḅᡠᨵ¶᪀*aᒹ¸¹*¶᪀d'¡¢'ᢣ»¼½⏣஺1-methoxybutane1-ethoxypropane1-methoxy-2-methylpropaneᵬ®¾nvrᏉv®rn1-ᵬ®-2-ᵬrn2-methoxybutane2-ethoxypropane2-ᵬ®¾naÀឋÂy8;᧜*dv¶r⏚2-v®rn2-methoxy-2-methylpropanepentan-l-ol6Hpentan-2-olᵬ®½¾Å2-ᵬ®-2•■ᵬrn1■ª⏣2.ª⏣ay8;᧜*d

350Hpentan-3-ol3-methylbutan-l-ol3-methylbutan-2-ol3-ª⏣3-ᵬ-1-¾⏣3-ᵬ-2-¾⏣ay8;᧜*d2-methylbutan-2-ol2-methyIbutan-1-ol2,2-dimethylpropan-1-ol2-ᵬ-2-¾⏣2-ᵬ¾⏣ay8¶᪀*d2,2-ᵬ-1-r⏣8.3ÈÉ£ᑡ¶᪀*ÊtËḄ?u஺AuÌὅḄᑖÎÏ^ᜧ'ᑣᑖ=°ḄÑÒ☢ÔÕ_'Ö×ᑖ=°ØᵨÚÕ_'uÛÊ^0BuÜὅ/ÝÞᡂᑖ=°à'ABØᵨÚáâ'Ê^[஺8.4£ᑡã8äḄ⊤æçvèéêÞᡂḄà஺B8.5ëᡂ£ᑡìᓄ:

36OOHa.b.CH3cH2cH20H_________CH3cCHc-CH3cH2cH20H---------------►CH3cH2cH20cH(CH?}OH/d.CH3cH2cH2cH20H_______--CH3cH2cHe%OHOH1]sc*H3f.CH=CH_________22HOCH2cH20cH2cH20cH2cH20Hg.CHCHCH=CH------------>-CH3cH2cH2cH20H3227Dh.CICH2cH2cH2cH20H____¨ᫀOH0a.CrS.P^b.CH3cH2cH20HîH2somCH3CH=CH2Bò27CH3CH-CH2KOH/Eto,CH30cHBrBr7c.ACH3cH2cH20H@3)2஺ᔩCH3cH2cH20cH(ó)2HBrCHCH=CHCH3CHCH332

37HBrB.CH3cH2cH20H-------------CHCHCHBr322ôH+ONaHOHõ7CH3CHCH3CH3cH2cH2Br.CH3CH=CH2CH3CHCH3T.MOHd.CH3cH2cH2cH20HCH3cH2cH2cH?Br஺ᘂ÷1■>CH3cH2cH=2-t!^lICH3CH2CHCH3îH2so4CH=CHøùKMnC)422CH2-CH2HOCH2cH20cH2cH20cH2cH20HOHOHHO+CIICICH2cH2஺2HOCH2cH20cH2cH20cH2cH20H22NaOHCICH2cH20H1)BHEtO^26,2g-CH3CH2CH=CH2CH3cH2cH2cH20H2)HO,OH-22h.CICH2cH2cH2cH20H____►ô8.6ᵨúû}ᨵÉüýþḄÿ␺ᑡᔜᓄᔠᱥa.HCmCCH2cH20HCH3cCCH20Hc.CH3cH20cH2cH3,CH3cH2cH2cH20H,CH(CH2)4CH33d.CHCHBr,CH3cH20H32ᫀa.Ag(NH)+b.FeClc.H2so4KzCnChd.H2sO43238.7ᑡᓄᔠᱥᔲᡂᑖᑁᑏᨵᑖᑁᏉḄ#᪀%஺0Hᫀa,b,d'ᡂ

38H-°8.9ᑏᑡ()Ḅ*⌕,ᱥᡈ()ᱥ:

39a.(CI^CHCH2cH20H+HBr-----------►/0ZnCbHl(23)----►e.(CH3)2CHBr+NaOC2H5---------►f.CH3(CH)3CHCHKMnCU,23OHOHHIO4CH3COOH+CH3CH2CHOg-h.HIO4CH3coeH2cH2cHO+BrA2j.CH3(CH2)2CHCH2CH3H2so4ᑖᑁῃ0OHᫀ:(CH3)2CHCH2cH2BrCHI3oCH3I

40(CH)CHBr+NaOC2H5---------►(CH)CHOCH+CHCH=CH32322532f-CH(CH)3CHCH3KMn5*CH(CH)3C-CH32323OHOH-Jg.CHC—CH—CHCH7^CH3COOH+CHCHCHO32332nOHj.CH(CH)CH-CH2cH3r⊟H2SO4ACH3cH2cH=CHCH2cH3+CH3cH2cH2cH=CHCH3322,;ᑖᑁῃ08.104;<=>?@⏣;BᵨDEᑴ✏HḄIᧇKᙠMNOᵫQ<=>RᓄᑴS஺᝞UV᪵SᑮḄ,YZ[ᨵ\3]^ᓄḄQ<=>RK_᪵`,YabᫀᵨNaOH0cd⃓fgh◀j<=>Rᑖ%kC5Hl0ḄA,mnopqrᵨstKAnH2s஺4ᐳvwᡂB஺ᵨxḄy═⏚|0cdᜐᳮBSᑮ,ᱥCoCnyỚ⏚rᵨSᑮCH3coe%CH3cH0஺BnHBrrᵨSᑮD(CsHuBr),`DnᐳvSᑮA஺AḄ#᪀Kᵨ()%⊤2஺答案ArcH3COHD.%Cஹ-\lC-CHCH3KC-CH2cH3ஹ/OHHCHCBr33ᑖ%kC7HQḄ✏ᓄᔠᱥA,nopq/()ᙠỚ⏚rᵨSᑮBC஺BmcDᓄqKnᓄrᵨ,w⁐஺Cn⏚⏣cdrᵨ,w⁐,

41A,B,CḄ#᪀Kᑏᔜ()஺ᫀc.CHI3᱐¡nὁ᱐£ᑖᑁ¤¥;¦:12©ὃᫀaஹIR®>ᱯ°±bஹNMR±☢¶·¸cஹIR®>ᱯ°±dஹNMR±Ḅᦪ¼ᑖ½¾13ஹ^CH-OHH3cNMR,À±611,ÂÃC-HḄ¼ᑖÅᔠn+1ÇᑣKᓄÉÊËÌᔠ〉஺IR,0-H,C-H,C-0ḄϱÐÑ;஺

42ÒÓÔÕஹÖஹ×9.1ᵨIUPACØÙÚÛÜ᝞UmḄÝÞÚÛᡈᑏ#᪀%a.(CH3)2CHCHOb.CH32CHCOCH3e.(CH)2CHCOCH(CH)2h.B—ßᓄàÕ33i.1,3—?âãÖj.1,1,1—ä—3—åÖk.ᵬ>Õ1.3—åÖÕᫀa.ç=Õ2;ᵬ>àÕ2-methylpropanalisobutanalb.èÕphenylethanalc.Qᵬ>èᵬÕp-methylbenzaldehyded.3;ᵬ>;2;=Ö3—methyl-2-butanonee.2,4;ãᵬ>;3;åÖ2,4—dimethyl—3—pentanonef.éᵬ>èᵬÕm-methoxybenzaldehydeg.3;ᵬ>;2-=êÕ3-methyl-2-butenalh.BrCH2cH2cH0(CH)CCHOI.CHCHCOCHCHO323220.àêÕpropenalãèᵬÖKetoneëìíîḄᑁ¤:o(E)-hept-4-en-2-oneheptane-2,5-dione02,5-ïãÖZðᡈEð-4-ê-2-ïÖ(Z)-hcpt-4-en-2-oneH一一一一-二”(S)-3-methylpentan-2-one(S)-3-ᵬ>-2-åÖcinnamaldehydeᾙ᪺Õ9.2ᑏóì;ôpDᑡᔜõᓄᔠᱥḄ#᪀%

43(E)-hex-3-en-2-one2-chloropentanal4-hydroxyhexan-2-oneOO3-oxopentanalö>ḄÂÃÊa,Â◞ÊB9.3ᑏᑡ()Ḅ*⌕,ᱥa.CHCOCHCH+HN-OH3232b.CI3CCHO+H0-------►2H+HCCHO+KMnO34Ad.CH3cH2cHONaOH1H+e.CHCOCH+CHMgBr65365HO20+HNNHCH265g-(CH)CCHONaOH33h.0+(CH3)2C(CH2OH)2/0HCIH+KMnO4CHOøù

44m.C”CHCH2cH2coeH3+HCIAn.CH=CHCOCH+HBrA23o.CH2=CHCHO+HCNNaOHp.C6H5cHO+CH3COCH3ᫀ:/OHNIIa.CH3COCH2CH3+HN-OHCH3CCH2CH32OHIb.CI3CCH0+HOCI3CCHOH2H’CHOKMnOHOOCCOOH4"OHd.CH3cH2cH0NaOHCHCHCH-CHCHO32CH3CH3CHCOCH+CHMgBrCHC—OH6536565C6H5O+HNNHCH265g-(CH3)3CCHONaOH.(CH3)3CCH2OH+(CH3)3CCOOHO+(CH)2C(CHOH)2/0HCI32l_l+஺ú2஺7_____HOOC(CH)COOH23KMnO4CHO-------------COOHøù

45ClICl-OHm.CIVCHCH2cH2coe+HCI---------CH3-CHCH2cH2coeH3CH3n.CH=CHCOCH+HBrBrCH2CH2COCH323/OHo.CH2=CHCHO+HCN_____NCCH2cH2cHO+CH2=CHQHNaOH/?ChC6H5CHO+CH3COCH3-----------►C6H5CHCH2C-CH3OH9.4ᵨûᓫᓄÉý␺ᑡᔜᓄᔠᱥa.àÕஹàÖஹà⏣çà⏣b.åÕஹ2.åÖ?åÖᫀa.AàÕABàÖBCà⏣CDçà⏣Db.AåÕTollenÿᑺB2—åÖC?åÖ9.5
ᡂᑡᓄ

46a.C2H50HOHCd.HCCH______►CH3cH2cH2cH20HCH3CH-CHCHOf.CH3cH=CHCH0OHOHg.CH3cH2cH20HACH3cH2cH2cH20Hᫀ:OH/O-CH3CHCHCHO9H,CH3cH=CHC8KMngci-ljCH-CHQHOH-OHOH»CFfeCH-CHCHOOHOHLIDMgDHCHOHBrCH3cᡈCFfeBr--------►CFbCfCbyVIgBr-^-------►CkfeCfCFtCFbOHCaChlCMH*EtO2)H+2

47᱐:hex-3-yne.HgSOJH2sO4/H2Oᑴᜓ2஺9.6ᑏ"ᵫ$Ḅ&'ᓄᔠᱥ*+,-ᑺᔠᡂ2./⏣Ḅᩩ23.ᫀ5ACHCHCHO+CHjMgBrBCHjCHO+CHCHMgBr32329.7ᑖ7ᵫ8*ᵬ8ᔠᡂ2.8':⏣CH2cH20H9.8ᑡᓄᔠᱥ;<=>?@ABᡈ?@C,=>@ABᡈ@CHIᑏ"J$Ḅ⏣*AᡈᑴᜓEFḄG஺ᫀ:a.@b.?@c.d?@A

489.9Kᑡᓄᔠᱥᑖ7LMN

49kỚḄqLUᐳstuᡂv⁐xy஺Ak{|⏚ᐳsiC(CH),C═⏚gᓄ510i*:⏚஺AḄ^᪀ᵫ;ᑖ"ᩭḄ.ឋᱥ<ᵨM¡*¢ᑴ᫏✏¤஺✏kn⏚.¥sgᓄᵫ✏ÍḄ;ᑖ"Ḅ✏Îᡂᑖ<>.ÏÐḄ✏®ᧇ<ᐸᑖeGfCHOOAjkÒÓÔÕḄÖuᱥ·ᵨ<¸¹ºu»¼஺Aj×ØḄÙÚᓄ²L1730UÛ⁐uᡂᑖeGfCHBrOḄB஺KAk═⏚NLU.¥siᑮgᓄÞᱥC,17302ᑖeGfC17H30O5஺¸᝞¦n⏚kA.¥s<ᑣiᑮ᝞Ḅmᐗ¨⏚5HOOC(CH2)COOHHOOC(CH2)COOH76KAMßà½ᓄ¾ᓄiᑖeGfC17H32஺ḄD,Dkn⏚siᑮHOOC(CH)COOH஺215ᑏ"ᮣͦ*B,C,DḄ^᪀G

50ooooáfâὅḄCH30-fäåæçæ'<¥ᓄ·ᵨ<èé>ê×iºuë᪶ᡂḄ&'ᡠîḄ²®eïᵯeñòó<ôõö'²ïḄ÷ᵯ₹஺16.Ò'ḄᱯúûüᜫḄt᎛18.aஹÿᔜᓄᔠᱥᨵᨵᑖBஹᓄᔠᱥᨵᐸ3Hᓫ3H2HCஹᓄᔠᱥᨵ6Hᓫ4Hᓫ019ஹ

51⏚ᐸᱥ10.1ᵨ"#$%&$%'᝞ᨵ)%*+,-ᡈᑏ,0᪀2COOHa.(CH)CHCOOHCHCH=CHCOOHd.CH3CHCH2COOH323Bre.CH3cH2cH2coeIf.(CH3cH2cH2co3஺g.CH3CH2COOC2H5h.CH3cH2cH20coeH3CONH2Cj.HOOCI=CCOOHk-:;ᵬ⏚ᵬ=Lᵬ⏚?@=HIHm.N-ᵬA@⏒Cn—r.ᶍs.;ᵬ⏒AE⏒AFᫀHa.2ᵬA@⏚2—Methylpropanoicacid'?I⏚Isobutanoicacid)b.:JA;ᵬ⏚(Lᩰ⏚)o-Hydroxybenzoicacidc.2—IO⏚2—Butenoicacidd3PI⏚3—Bromobutanoicacide.I⏒QButanoylChloridef.I⏚RButanoicanhydrideg.@⏚E=Ethylpropanoateh.E⏚@=Propylacetatei.;ᵬ⏒CBenzamidej-SIO⏚MaleicacidCOOCH3I.HCOOCH(CH3)2m.CH3CH2CONHCH3COOCH3COOHHo/^^0COOHureaoxalicacidformicacido.P-COOHHOOCsuccinicacidfumaricacidq-10.2TU.ᑡᓄᔠᱥᢥ⏚ឋZ[ḄS]᣸ᑡ:a.CHCHCHBrCOHb.CH3cHBrCH2co2Hc.CH3cH2cH2co2H322

52d.CH3cH2cH2cH20He.C6H50Hf.H2cO3g.BrCCOHh.H0322FᫀH⏚ឋ᣸]g>a>b>c>f>e>h>d10.3ᑏ,`ᑡabḄc⌕eᱥHOCH2cH2coOH_UAIH4__d.NCCHCHCN+H0_Na°H_a()j£222CHCOOH2e.Ba(OH)CHCOOH22fLAICICH3COCI3g-(CH3CO)2Oh.CH3cH2coOC2H5_N.g஺2h*i-CH3COOC2H5+CH3cH2cH20HJ-CHCH(COOH)j►32k.COOH+HCI

53o.?H2cH2coOC2H5NaOC2H5CH2cH2coOC2H5----------->q-CH2'COOCH-2+HNCONH2522Fᫀ:HOCHCHCOOHLiAIH4,HOCH2cH2cH20H22d.NCCHCHCN+H0_NaOHf-OOCCHCHCOO'»HOOCCH2cH2cOOH22222h.CH3CH2COOC2H5NaOCzH”CH3cH2coeHCOOC2H5CH3

54CH3COOC2H5+CH3cH2cH20HHCH3COOCH2cH2cH3+C2H50HCHCH(COOH)ߟ*—►CH3cH2coOH+C0j.322k.I.COOH+HOCH2cH20Hmn.o.10.4ᵨkᓫᓄlm&␺o`ᑡᔜᓄᔠᱥ:aCOOH].CHCOOH2COOH"CHCOOH2c.(CH)CHCH=CHCOOHpCOOH32FᫀHa.KmnO4b.FeClc.BrorKmn0d.জFeCbঝ2,4-qA;r324ᡈk/NaOH10.5sᡂ`ᑡuᓄ:

55COOHa.OOHCHCHCHBr--------CH3cH2cH2co0H322g-HCCHACH3coOC2H5CH3cH2coOHCH3cH2cH2cH2coOHJ-CH3COOHCH2'COOCH-225CH2COONH4CHCONH22CH3cHCOOC2H53CHCHCOOH32

56Fᫀ:CHCHCHBrCNCHCHCHCNH,CH3cH2cH2coOH322322H02(CH)CHOHCrC)3.(Py*(CH)C=OHCNஹ(CH)C—CNH+(CH)C—COOH32323232OHHOOH2O°e.(CH)C=CHHBrr(CH)CBrMg►(CH)CMgBr1)C02(CH)CCOOH322333333EtO2)H+/HO22f0v3wMCOOHacoohBrCH3CH2OHg.HCCH———►CH3CHOKMnCU,CH3COOH---------------------►CH3coOC2H5H+,Hg2+H+jh.CXHN°3rHOOC(CH)COOH—■24\o=°i.CH3CH2COOHLiAIHjaCH3cH2cH20H—tlCH3CH2CH2Brz°»CH3cH2cHzMgBrVKMnO4u»CH3cH2cH2cH2cH20H---------.CH3cH2cH2cH28OHH+ᡈCH3coeH2coOC2H5.x஺y------CH}OH-^-CO-CH-COOCoHc--------►CHofCHnkCOC2)CHCHCHBrCHCHCH322223j.CH,COOH~2rCH2COOHCN_CH2COOH*PClrCNjEtOHߟ.j-CH(COOCH)22520kCoNH3CH2COONH4nCHCONH22,CC&OTUஹ/^/COOH7^\)0CCH31m.CHCHCOOHSOC]»CHCHCOCI3232CHCHCOO-ீy32n-CH3cH(COOCH5)20°LCH3cH2coOH22)H+3)A

5710.6᪵T⏣ஹ⏚ᵬ;ḄᔠᱥᑖᑮᔜḄᑖ?FᫀH⏚3⏚B⏣ALC⏚B⏣NaOHᵬ;ᵬ;ᨵᬳ⏣A+Hᑖ␺o10.7ᑏ,ᑖ2C5H6஺4Ḅ⛳ᐗ⏚Ḅᔜ?᪀஺᝞ᨵ?᪀z,E᪗¢,ᢣ,¥¦᧕¨ᡂR஺FᫀHCOOH©ªᑮ«¬☢ᑖ2®¨ᡂ⏚R¬¯ᙊ±²³ᐗ±ᨬµ¶¨ᡂ⏚R·ᙊ±hᐗ±¸¹஺º»Z½¦᧕E½¦᧕·E½◤⌕À᪀½Áu◤⌕Â᜜Ḅ¶Ä஺ᐸ¸¹ឋÅÆÇ-᧕ᡂR'E-᧕ᡂR'Z-᧕ᡂR'E-᧕ᡂR10.8ᓄᔠᱥA,ᑖ2C4H6஺4,Èɵᑮᑖ2c4H4஺3ḄB,TApÊÄᵬ⏣ËÄÌ⏚ÍÈÉᑖ2CHOCOBpÊÄᵬ⏣ÎᵨÏᑮC஺ApLiAlEL
Îᵨ6104µᑖ2C4E0O2ḄD஺ᑏ,A,B,C,DḄ0᪀2ÐÑÒuᓄḄab2஺FᫀH00IIHC"COCH3D.CH2cH20HA.CH2COOHB.C.2CHCOOHH2C^COCHCH2cH20H320010.9AÓ᜜AᱯÕÖ[k×

58BNMR,@ØᨵᑖᵬAᓫCNMR,Øᨵ=ᨵDÓ᜜AᱯÕÖ[k×10.10ChemNMRH-1Estimation2.017.21

59ÙÚ⏚11.1ᑏ,`ᑡᓄᔠᱥḄ0᪀2ᡈ$%஺CH3cHeH2coOHCHCCHCHCOOH322m-cin-OFᫀHm.3—QI⏚(3--Chlorobutanoicacid)n.4--ÛÚÜ⏚(4-oxopentanoicacid)2-oxopropanoicacidoxaloacctatedCaution:AnetchargeappearstobepresentCHOICOOHtartaricacidformylfbrmicacidEÝ⏚f2OO2-hydroxysuccinicacid2JAᴁß⏚(L)acetoaceticacidD

60OH11.2ᵨkᓫᓄlm&␺o`ᑡᔜᓄᔠᱥ஺a.CH3cH2cH2coeH2coOCH3l|ICHCHCOOH3^^COOHohb.CH3cH2cH2coeH3CH3coeH2coe%FᫀHa.CH3cH2cH2coeH2coOCH3CH3CHCOOHOH11.3ᑏ,`ᑡabḄc⌕eᱥHa.CR,OOC2H5àbCH3COCHCO2CH3áNaOH&2c02cH3jc.CH3CH2CHCOOH—ᓃ——►OHç/COOCH"COCH3jd.kJUtJUri3èH+

61e.jf.HOOCCH2COCCOOH——CH3NaOH-HO2g-CH3cH2cHec)0H*Clh.CH3cHeH2coOHjOHi.NaOH-H2OjCH3èH2so4j.CHCHCCOOH32jOHèH2so4k.CH3cH2coe02HAI.CH3cHeOCO2H------>CHj3m.L'COOH—^^^COOHn.1)NaOH,A2)HCI,j*஺CH3cH2coOH+Cl2ᫀ:

621)èOKAa.CH3COCHCOOC2H5CH3coeH2cH32)H+,H02CH3b.CH3COCHCO2CH3áNaOH?H2coO+CH3coer+CH3OHCH2co2cH3jCHCOO-2oCHCH2cH3co+CHOH23CH2cH2cH3+CO2f.HOOCCH2COCCOOHCH3COCH(CH3)2CH3NaOH-HO2g-CH3CH2CHCOOHCH3cH2cHec)ONajClOHh.CH3CHCH2COOHjCHCH=CHCOOH3OHNaOH-H2OCH3CHCH2COONajCHOH2èH2s஺4CH3CH2CCOOHCH3CH2CCH3+HCOOHjOHèH2so4k.CH3cH2coe02HCH3CH2CHO+C02jI.CH3CHCOCO2HCH3CHCOOH+COjCH3CH3

63o஺CH3cH2coOH+Cl------;------►CHCHCOOH23Clᙠë᱐íîbᨵµ⊈Ḅ⚪ñ]òÅÆó¬nbḄm┯õö÷:LNaOH,ÈÉ2.H+,ÈÉ11.4ᑏ,`ᑡᓄᔠᱥḄØ2pO⏣2Òøù⊝"஺a.CH3COCH3b.CH3CH2-----C=CH—COOCHc.CH3COCH2CHO3OHd.CH3COCHCOCH3e.CH3cH2coeH2coeH3f.CH3cH2coeH(CO2c2H5)2CH30h.g.CH3COCHCOCH3COCH3COCH3Fᫀ:

64a.CH3COCH3b.CH3CH2C=CH—COOCHCH3CH2--CCH2—COOCH33OHoCHCH=C-CH2COOCH3"I"36HCHCH-C-CH=C-OCH323OHOI11CH3COCH2CHOCHC=CHCHOCHCCH=CHOH33OHd.CH3COCHCOCH3CH3C=CCOCH3CHI,3CHOH3ICH3cH2coeH2coeH3■-CHCHC=CHCOCH■■■CHCHCOCH=CCH323323OHOHOH'CH3cHRCH2coeH3CH3cH2coe#$CH2OHCH3cH2coeH(CO2c2H5)2CH3cH2c=C(CO2c2H5)2.CH3cH2coe=C-CO2c2H5OHSc2H5COCH3g.CH3COCHCOCH3CHCOC=CCH33COCH3OH11.5sᡂ`ᑡuᓄHa.BrCH2'CH2-2CH2co2Hc.CH3COOH-------------►CH3CHCOOHdCH3COOC2H5_CH3CHCOOHFᫀ:

65NaOHBrCH(CH)CH2COH2222OCO2CH3EtOC2H5COCH1)èOH,CH2COCH3b.23CICHCOCH2)H+.A23CH2COCH3CHCHOH1)NaOC2H5CH3COOH32NaOC2H5CH3coeH2coOC2H5--------------------------CH3coOC2H5H+j2)BrCH2CH2CH2BrOII1)QH-CH3—C—COOC2H5CH3CO2)H+,jzgc71)NaOC2H5ᡝ3d.CH3COOC2H5NaOC2H5»CH3coeH2coOC2H5'CH3coeHCOOC2H5COCH3_1)NaOC2H5CH3CCOOOC2H51)á0HgCH3CHCOOH2)CH3cHec)0C2H5CH3cHeOOC2H52)H+CH3CHCOOHBrBḄabᱥüýE⏒E⏚E=Ḅ0᪀pᓴÚ@Øabᯠ
ᑖ஺᱐Cd᪵᝞ᦋC.D.ᐜ⏚"ᡂ$%⏚%&'(%C)᯿P216+⚪-ᐭ13/0$1(D23-ᐭ2-50$⏚&'1-5ᵬ17᝞8-ᐭ9:;<ᑣ◤⌕ᐜ-ᐭ@ឋBஹDEᜧḄH:IJKLMῃOPᡂQR)᯿P216+⚪⏚"ᡂ$%⏚%&'ḄSTC12/PNaOHH+HC——COOH-----------►HC——COOH------------------►H2c-------C00'------------►H2c——COOH32INaCNIIcNCOOHHC——COOEt2IEtU&;ḄVᑏXYEtOHU&⏣[᜜9])᯿ᦟᩞP216`Pᡂ஺

66bcᓄᔠᱥ12.1ᑏgᑖhUC4H11NḄiḄᔜkl᪀Dnopᢣgᔜrstui஺NH22-methylpropan-1-amine2-methylpropan-2-amineA^-methyIpropan-1-aminediethylamineN7V,7V-dimethylethanamine12.2novᑡᓄᔠᱥᡈᑏgy᪀a.CHCHNOb.HC-^^-NOC.3223Bre.NHCOCH3f.CH3cH2cH2CNg.0i.[NHJ.(CHCH)N-NOk.322om.z{in.&⏒}~o.ᫀa.;&1b.p—;ᵬc.N&;id.ᵬc⏚ᡈᓄcᵬe.&⏒if.ᨴ☘g.;h.1,6%ii.%⏒ij.N-;%&ik.ᓄᓝ%1;☩;%ᵬ

67I.[(CH)N+CHCHOH]OHm.HOCHCHNHn.[(CFbN,CH2cH20coeH^OH3322222HONHo.HOCH(OH)CHNHCHp.(CH3)CHCHNH2q.r.N,N—%ᵬ;&i2322HN-C-NH22HO12.3vᑡt:ᓄᔠᱥᙠ᧜l᪀Da.CH3NHCH2cH2clb.(CH3)2hT(CH2cH2஺)2clN-CHd.CH2CHCH33NH2ᫀa,dᙠ஺aḄ᧜l᪀DᙠKᩩ¡v¢£᧕¥¦ᓄ஺12.4vᑡD§¨©ᙠḄªa.%ᵬiḄM«¬b.Ḅ%ᵬiᫀH0²³HHC3XO—H--0—H---H3C-N-H-O;-HaC2N-H—N--H-N---S®HHH//THCHCIII33aᨵᵨHIJkªb.±ᨵIkª12.5᝞´µvᑡ¶·a.¸i(C6H5cH2NH2)Ḅ~ឋº1;i;»º¼i஺b.vᑡᓄᔠᱥḄpKaUpK=13.0pK=9.37pK=8.70bbbᫀa.½Uᙠ¼iN¾º¿ÀÁÂᐸÄᵯh©º¿ᐳᡠÉ~ឋº1;i;Ê஺b.ONHQ^NH;ᐹᨵÌḄᔾᵯhᦔR஺-NH2NÄᵯhzᙢÐᔣ¿,22ᡠɺiÓ,ᐸ~ឋÔ஺»H3C-^HNH2ᵬ;ᐹᨵÕḄÖᵯhᦔR×-N”NᵯhØÙÚÛÜᡠɺiÓ,ᐸ~ឋᶍÌ.12.6ÉQR⊤à᝞´ᵨ(+)⏀ã⏚äᑖåæiᫀ

68(t)-CH3cH(N”)CH2cH3ç)⏀è⏚7+Ii7+I⏚;ᱥᳮឋë¨Ii7+I⏚äᑖ,»ìᑖíÜNaOH᪆gi.12.7ïi7I:bஹkஹeåi7Ihஹiñi7Iaஹcஹdஹg^jò╄7I:f12.8vᑡᓄᔠᱥt:¨ÉUô᪶öᑺ?ᫀa,b,c,d,e,f12.9Pᡂvᑡ¦ᓄ:ᫀ:

69C.CH3COOHù5■(CH3CO)2ONH3-CH3CONH2CH3COCI"3ACH3CONH2CH3COOHNH3'CH3COO-NH4+ú»CH38NH2CH3COOHd.CFbCI-bOH▬ü"CHjCHO1)Cl^^MgPlChbCH(OH)ChCHfeSQ9LCឃCHC*CF%2)H61HCINWMqCHjCHCfiCI-b-~+b-----------C(Cg----------►CHjCH?MgCIEfeO+CHCHCHCH323NH2ᔢ
NᵬᑖᑡᑺḄ⌕12.10ᱥ᝞!"#Ḅ$஺a.&ᵬ⏒(b,*⏚,c.-.Ớᵬ0d,1&2ᵬ⏚,e.&3⏒(f.4⏒(g.56⏚h.78⏚9ᫀ;

70b.d.one12.11ᵨᓄDEF␺ᑡᔜIᓄᔠᱥ;a.1ᵬ&LNᵬ&L&ᵬ⏚N1O&ᵬ⏚b.QᵬL8⏚8Rᓄ*᪶9ᫀ;AgCI|TUAᑖXb.(CH)N.HCI(A)gNO-33A3ᡈὅᵨNaOH—(CH3cH2)4N+Br-(B)AgBr|VBᙳ\ᵫ^QᵬLb.p.3࠷,c!⍎efgc!hᑖi^NaOH,ᡠmᵨAgNOn,o␺pq.12.12ᑏeᑡḄ⌕ᱥ:

71a.(C2H2+CH3CHC4---------Brb.[(CHsWCHcHcgᵨ0-+NaOH2zaGHsbN+C᱐HCu--(CH5ᾢ—B[2BrCHjb.[(CFbN+cmCHcᵯcnyc{+NaOH[(C/bN+ChtCFbCHcH3]+CF+Na++OH2212.13N-ᵬ&L}~ᨵ.&LNN,N2ᵬ&L,᪵NᵬL?9ᫀ;ᵨHinsberg.ᑖN␺Ḅ◀CNaOH◀EyNHC%A(D)12.14ᑡᓄᔠᱥᢥឋḄ᣸!J;a.CHSC0NHb.CH3CH2NH2c.H2NCONH2d.(CH3cHJ2NHe.(CHCH)INOH232

729ᫀ:ឋe>d>b>c>a12.15£Lஹ⁚⏥§ᵬ&¨Ḅ~ᔠᱥᑖ©QªḄIᑖ஺12.16ᑖ«¬©CMsNḄA,!i^78⏚஺A56⏚ᙠ®¯oᵨ°e±²f³´ᑮ¶ªᨵ·ᱥfᐸ}•ªB!º»Ớ¼஺BN½¾⏚ᐳÀ´ᑮC(CM஺fC!Á═⏚Ã⌨⁐fÆÇḄᱥÈ*⏚N2ᵬ4⏚஺ÉÊAḄË᪀¬f³ᑏeÉÍ-஺9ᫀ;Q=-6/2+2+1-15=o⛳NL2BᐹᨵCHCHCH(cº»Ớ¼)349OHCH3C(CHi2)KMn°4»CH3COOH+CHCHCOOHᡠmC©CH3cH=CHÐ63CHCH33/CH3᎔ÉÒBCH3cHeH2cHOHXCH3AÓ3CH3cHeH2cHNHXCH2317\NTIᙠ3300ÔÕᨵÖ×OHḄᔾᦈÚfÛ\§pÜpÝ┦fᐸ}ßL©ᓫÚfáL©âÚfãLäᨵᔾᦈÚ18ஹ0Hᔾᦈåᜧ

73ç¾Nçèᨵ·ᓄᔠᱥ1ஹᶍ2ᑡᓄᔠᱥᢥ⏚ឋḄ᣸ᑡ;3ᑏeᑡḄ⌕ᱥ;SCHCHCOOH2a.|NH[HI2SCHCHCOOH2NH2b.+KOH-CHSH2c'CHSH+HgOCHOH2CH3cH2cH2cH2sH"03Ad9ᫀ:SCH2cHeOOHCHOHCHOH22

74d.CH3cH2cH2cH2sH_"03ACH3cH2cH2cH2so3H4ஹê-ëìḄíᵫîᔠïᡂḄÁᑖ«ᓄᔠᱥfñ^ᐸ}òᐭôõὶᑺïᡂô÷øùúË᪀fê-ᓄDû⛲ýþÿ
⏚⊤ḄᣚḄ□ᡂ□ᣚ᪛ᾦ᪶ᣚḄ▢ᡂ▢ᣚ᪛ᾦ஺5ஹᶍ6#ᢣ%&ᧇ(ᐸ*+,-ᑺᑏ01ᑡᔠᡂ45஺a.ᵫCH3cH2cH2cH20HᔠᡂCH3cH2cH2cH2sC^CH2cH2cH2cH3b.ᵫ

75;<ᓄᔠᱥ1ஹᶍ2ஹᶍ3ஹᶍ4ஹᶍ5ஹᶍ6ஹᶍ7ஹᶍ8ᫀ:a.b.f.ᨵ@ABC஺DEFGHIJKLMaN@஺91ᑡᓄᔠᱥ,RST&UVWᱯRSYZ[\PCH3C----------b./OH~~Id.fgHa.|c(CH0H)3c=o(CHOH)3(CHOH)3HC---------OCH2OHHC---------OCH20HICHOHCHOH228ᫀ:b஺10R]D^_H`HNC>3aᓄbcᡂᑁeA`f⏚?8ᫀ:D-ij`D--Fk`

76I11mSᓫ`oJpqrsᵨuvᑮx᪵ᨔ{Ḅ|ᐸ}Sᓫ`ḄᢗMC"OHᑏ0ᐸ*S᪀ḄᢗM஺8ᫀ:CHOH2=012ᵨᓫᓄ␺1ᑡᔜᓄᔠᱥa.ℍ⃔`oⅅ`b.oc.ᱛ`od.ℍ⃔`o`e.ᵬ-P-D-¥ᗏᵞ☄`᧖o2-0-ᵬ-B-D-¥ᗏᵞ☄`8ᫀ:a.Bendict-ᑺ¯b.Ic.Id,Br-H0e.Tollen-ᑺ222213.01ᑡ¶·Ḅ¸⌕ºᱥᡈ¶·ᱥ:NaOHHO2CHOH2,OHAg(N4)2|—0CHOH2CHOH3+

77CHOCHOHCHO2a.NaOH=Q—MO'f[ICHOHCHOHCHOH222COOHb-Ag(NI"2+o——CHOHCHOH22CHO\COOH—\HNO3_CߟH20H/COOH-᱐ᦟᩞ⊡ᐙ⚪14ᑏ0D-ᵞ☄`Æ1ᑡ-ᑺsᵨḄ¸⌕ºᱥ:a.Br-HOb.HN0c.C2H5OH++

78COOHCOOHCHOAcO-AcO--OAcCOOH-OAcACHOAC2b.HNO3e.(CHCO)O32CHOHf.NaBH24}h.ÐᓄØᓄCHoOH-------------------g-HCN4Õ⏚ឋ<×COOHCOOHCHOHCHOH2215ℍ⃔`ḄÙᐗÛ{FGHÜIJᡂᵞஹᵬᓄஹ<×ஹaᓄÝÞßᵫᡠvºᱥáâḄ¿ã226⚓¾஺᝞ℍ⃔`{ᡂḄÛ{FGHÜæᐗÛᑣè᝞Þßᜐᳮu·vᑮZ[ºᱥ\8ᫀ:CHO-OCH3CH3O--0H-OCH3CHOCH2316ஹᶍ17D-ëi`oD-ìí`ÜᔲᵨHN03aᓄḄᩭð\8ᫀ:D-ëi`oD-ìí`ᵨHNChaᓄḄᩭð.DaᓄºᱥñὅᨵAᐝ,uὅôAᐝõö.18÷ℍ⃔`T&vᑮᓫ}Ḅℍ⃔`⏣A,ù÷`T&◀vᑮA᜜Tvᑮü}`⏣B,Z[\AÆBÜZ[ᐵþ\8ᫀ:D`ḄT&ᡠ{ᡂ}Sÿឋ
,ABḄᐵᔣ᪀.

7919ᑡᑺᜐᳮ!"᝞$%&Ḅ'ᑏ)*ᱥḄ,᪀-ᡈ/ᑖ,᪀-஺a.2345⏚78b.89c.8
⏚:9;ᵬ@ABCᓄ:EᫀG20ᑏ)ᵬHIJKLMᑡᑺᜐᳮᡠO*ᱥḄ,᪀-஺a.234P⏚78b,4BCᓄ:78EᫀG21ஹᶍ

80ST⏚ஹUVWXI1,2ᑏ)ᑡST⏚ᑖY23P⏚ᡈ23BCᓄ:9;

81d|S⏚HOOC
CHCHCOOHIP3.22PH=3HOOC
CHCHCOOH2222NH2+NH35.ᑏ)ᑡ!Ḅv⌕*ᱥa.CH3cHe02c2H5+H0Hfl}2NH2b.CHCHCOCH+JCH3co%O3225NH2c.CHCHCONH+HN0J23M-----►322NH2d.CH,CHC0NHCHC0NHCHC00H.HoHa22,IINHCHCHJCHM2232e.CHCHCOOHCHCH,COC1____3+3NH.2£JS⏚M+CHOHJ23MHC13g.JS⏚M+CH3cH2lJ23M_Ah-JpS⏚Mbai•]S⏚2T22k.NH2cH2cH2cH2cH28OH1.CHCOOH2SOC1_____►2NH.HCI2EᫀGa.CH3cHe02c2H5+H0H,CHCHCOOH23NH+NHCF23b.CH3CHCO2C2H5+
CH3CO2OCH3fHe02c2H5NH2NHCOCH3c.CH3CHCONH2+HNO2J23M----►CH3CHCOOHNHOH2

82d.CH3cHeONHCHCONHCHcoOHHO_2L_►CH3CHCOOH+HN+CHCOOH2232NHCHCHCHM2+NH2233+
CHCHCHCHCOOH322+NH3e.CH3CHCOOH+CH3cH2coe1CH3CHCOOHNH2NHCOCH2CH3f-JS⏚M
CHCHCHCHCOOH+CH3OHJ23MHC]
CHCHCHCHCOOCH3223223NHNH22g-JS⏚MCH3CH2CH-CHCOOH+CH3cHJJ23M_CH3CH2CH-CHCOOHCH3NH2OCHNCH2cH3
3llh.JpS⏚MCHjCHCOOHH33CஹHC,CஹNHᨔஹCCHஹCH3NH2]S⏚HOHQ^CHCHJNHMCOOHBT-HZR22J-JᑁS⏚MCH3fHeOOHNH2k.NH2cH2cH2cH2cH2coOH1280H+,CHCOC1soc22NH.HCINH.HCI226ᓄᔠᱥᑖ-C3H7O2N,ᨵᐝឋ&ᑖYNaOHᡈHC1ᡂP&⏣ᡂ@,HNC>2Zᵨ)ᑏ)ᓄᔠᱥḄ,᪀-஺EᫀG2n+2+N-▭Bᦪ_3X2+2+1-7_fQ=ߟ22ST⏚
ᨵᐝឋ!pS⏚CHCHCOOH3NH27ᵫ3-ᵬTL⏚ᔠᡂzS⏚*ᱥ=ᔲᨵᐝឋ""EᫀGCH3cHeH2co0H.CHCH-CHCOOHNHஹ.CHjCH-CHCOOH?CHCH3aCHNH332᝞$ᙠ£¤ឋᩩ¦OᑮḄ*ᱥ£ᐝឋ,¨ᙠa-©ª⏚ᡂḄ«b¬£⌱¯ឋ.8☢Ḅᓄᔠᱥ=>VஹV±=²V"ᢣ)ᐸuḄV´ஹN-µAC-µST⏚V%¶·=⏚ឋḄஹ¸ឋḄ±=uឋḄ"

83CH3M2CHCH2cHeONHCHCONHCH2co2HNHCHCHSCH2223Eᫀ:V,NµS⏚,CµᵞS⏚.uឋ.9.10º»ᑡV¼)cᑏ»½஺CHOHCH3cHNCHCONHCHCONHCHCOH222a-IIb.HOOCCH2CH2CHCONHCHCONHCHCOOHCHOHCHCHCH2232NHCH2c6H52EᫀGa^S⏚bᵞS⏚bS⏚cᑏG^bᵞbb|S⏚b¾pS⏚bnS⏚cᑏG|b¾pbn11.12UV⏚9¿ÀÁ¸uÂ9¿<ᨵ)஺ᵫ%O)ᨵᐵUV,᪀ḄÃÄ"EᫀGUVÅᨵÆÇḄÈTÉTNAyᡂ⏒Ë.13VÌᐰ9¿ÀOᑮᵞS⏚ApS⏚஺ÎVÏÐ⏚ZᵨÀÁ9¿ᑣOo⏚ஹpS⏚AᵞS⏚஺ᑏ)VḄ%&,᪀-஺EᫀGpbᵞbpᡈpbpbᵞ14ÒVÓ/ᑖ9¿OᑮᑡbÔVG^-\-¾pᵞ-¾p-^\-¾p-ÕÕ-\-\\-ᵞ-¾p\-\-ᵞA¾p-^-\஺cᑏf-᣸)ÒVuST⏚Ḅ×Ø஺Eᫀ:Õb\bÙbᵞb¾pb^bÙb¾pbÕ

84Úᾦᓄᔠᱥ1ஹᶍ2ஹᶍ3ᵨᓄefg␺YᑡᔜkᓄᔠᱥGa.Üᾦ⏚Â∑b,Þ⏚ᵞÞ@ÂÜᾦ⏚ᵞÞ@c.ÏÞ⏚ÂÏßÞd.àᾦ⏚:ÂᓝâãT5⏚:e.äÞÂåÞEᫀGa.KOH,Ab.BrorKMnOc.KOH24d.Ca(OH)e.BrorKMnO2244.ᑏ)ᵫæ᫂Þ⏚ᵞÞ@ᑴᜓ⊤☢ឋᑺᓝâãT5⏚:Ḅ!-஺EᫀG0CHO-C—(CH)CH=CH(CH)5CH22723I°KOHH+CHO-6—(CH)7CH=CH(CH)5CH3----------►-----►CH(CH)CH=CH(CH)COOH2232527IoíIIICHO-C—(CK)CH=CH(CH)CH227253--►CH(CH)COOH"Al"aCH(CH)ICH,OHH2S04>CH3(CH)|4OSOH32I432423CatNa°HCH3(CH)CHOSONa2l4235ᙠîïðஹñòóôõUöᾦ÷Å3ḄøùuAúûᡈᓄᝢùuýᵨᓿÿᾦᩭ■ᑖḄ᪷ᓿᾦḄᱯឋᫀᓿᾦ᪀!ᨵ#$%!ᨵ&$'()*+,-ὅ/0Ḅ12ᙠ45஺68ᑡᓄᔠᱥ=>ᨵ⊤☢AឋᑺḄCᵨCH3a.CH(CH2)5CH(CH2)3OSOKb.CH(CH)CHOH3332162c.CH(CH)COOHd.CH(CH)CH~SONH3216328234ᫀaஹdᨵ⊤☢AឋᑺḄCᵨ஺74GH᪀ḄIJᾦK⏚ᵞNᨵOᐝAឋ஺+ᐸḂᓄST⏚ᓄUᑮWᾦ⏚X⏚,ᐸ᥅[\]21஺ᑏ_(ᵞNḄ᪀`஺ᫀ

85oCHO-C—(CH2)7CH=CH(CH2)7CH32I?*CHO-6—(CH)CH2143IoIIICHO-C—(CH)CH221438c∑Ḅ•>f⌕ᡂᑖᓝj⏚ᓝjNk)lᵨCmḂXᓄᝢoḄpqᑺ஺r᪵*tWᾦ⏚ᵞN]u4Ḅᨵvwᧇᔠᡂkᫀ0CHO-C—(CHM4cH32nKOHCHO-€—(CH2)I4CH3----3CH3(CH2)14COOH{%CH3(CH2)14CH2OHIoIIICHO-C-(CH)1CH2243CH(CH)COO(CH)CH321421539∑Ḅf⌕ᡂ~IJᾦK⏚ḄIJ⛳4ᐗ⏣NᐸḄᾦK⏚⏣ᜧᙠᓝj*,!ᨵᏔᦪwᨬḄ]W⏚ᓝj⏚ஹᓝj⏣ᓝj⏣tᓝ⏣஺ᫀ]b18⏚22⏣ᙳ]Ꮤᦪᜧ16,a]4⏚36⏣c]17⏚23⏣஺10ᾯ¡ᾦ¢£¤¥¦UᑮḄ4§♆©ᾦ஺᝞«+k¬+Uᑮ=®ᱥCHOH2IJ—OOCHCHNHCO(CH)22CH223\|/?H0H|CHIICH(CH)CH2123ᫀCHOHHOCHCHNH222I)—OOHCHOH\|7+QH+HOCO(CH)CH3222ICH(CH)CH2123118ᑡa-dº>᪀`ᑖ»ᵨ1-4=4>¼½⊤¾1¿ÀÁ4,2,0ÂÃÄ2¿ÀÁ2,2,1ÂÅÄ3¿ÀÁ3,1,1ÂÅÄ4¿ÀÁ2,2,2ÂÃÄᫀa—4b-(2)c—(3)d—(1)12ÆᑡᓄᔠᱥḄÇÈ$ᡈÀḄὶË`Ì`ÍÎ`?

86b.HOHCH3ᫀ:aÎbÌcÌdÎeÎfÎ131-isopropyl-3-methylcyclohexaneᓫÀÒl-isopropyl-4-methylenebicyclo[3.1.0]hexane¿ÀÓdecahydro-4-isopropy1-1,6-dimethylnaphthalene.....$ÔᓫᐗḄ¥ᔠᨵÕᩖ஺×C⌕ØÙᶍÛ

8714.ᑏ_ↈ₹⏣Ḅt>Þ᪀ßḄ᫹`᪀á×âᑏ_ã᧜ß஺ᫀ15hexadecahydro-1//-cyclopenta[a]phenanthreneC]7H28ExactMass:232.22Mol.Wt.:232.4m/e:232.22(100.0%),233.22(18.4%),234.23(1.7%)C,87.86;H,12.14åæᓄᔠᱥçèéê⏣ᓄᔠᱥᐸ$Ôëì᝞íᡠ¾஺ïðñᑣóôÔ315⚓஺16reunoiö÷A]ÒéᓄᔠᱥøùÆ÷]ºÒéᓄᔠᱥᙠúᱥßᑁøùÆ÷üýlþᓄ]ö÷A,ᐸᳮ
஺ᐹᨵḄᢙ⊦ὁᢙ
஺17ᓫA,ᑖCIOHBᓄᓄ!ᑖC10H22Ḅᓄᔠᱥ஺ᵨ%═⏚()ᓄA,!+CH3coeH2cH2coOH,CH3coOH,CH3coeH3,-.AḄ/᪀஺1ᫀ3

88HHH22H3c—CH-C-----C-------CCHCH3456H3c—C—CH318✏9:;<✏=ᧇᑖCHO,?@ABCᑺEᵨ!ᑮ✏⏚CHO»101810182G%═⏚()ᓄ✏9!ᑮHI@HO2CCH2cH(CH)CHCHCOHOᑏK✏9Ḅ/3222᪀஺1ᫀ3HH/CH322HOHC——H2cCH-CC------CCஹICH3CH3ᑭᵨNO⏣ḄQRS⏚ឋᵨNaOHUVWᑖX

891ᫀ:Cl^yk/OCOCHc.3ZA/-A)oCH3coeH,tUE\/ஹ0H'21ᙠ16.20(c)]!ᑮḄᎷ_`ᐲIᙠ⏚ḄᓄlfGᐵnoᡂ_`ᐲIḄa-,B-r

90ᩖnᓄᔠᱥ1ஹᶍ2ஹᶍ3ஹᶍ4ஹa~vᱥ]ᗲnឋ;Nᐗn6ᾦឋᔠឋVg⏚b᪶⏚Ḅ⌕ᡂᡂ;vᱥSឋᗌnឋncឋ;N6¡⏚ឋ;N6¢ᨵឋᔠឋVg⏚cᔩᖹ⌕Ḅvᱥ;NឋRS¡⏚ឋcឋ஺ᓽfVg⏚¦fVgd§I¨✏ᧇ6gḄ¡⏚ឋfVg5ஹᶍ6ஹᶍ7ஹᶍ8ஹᶍ9ஹᶍ10ஹ©⏚ª«¬⏚®

91V+KOH+HO2H11ஹ]N=Ḅ¯°ᵯ²@ᐳᵐcµ¶ᔠ·¸¹ºᑣ¼½¾N=ឋ¿ᵫgᐳÁᦔÃÄžN-H]N°gHḄᔾÇÈÉÊË!HÌ᧕ÎvÏX⏚ឋ஺Ðn]N=ÑÒ;pᵯS=ÑÒ;°¯ᵯoᡂ¶ᔠ·¸¹ºᑣḄᐳÓcµÔ¿N=ᒕÖ;°¯ᵯS=ᒕÖ;°¯ᵯᙳឋ஺12ᶍ13ஹa®lØᔵ@«¬⏚ÎvÚᓄÉè◤⌕°ÜÝḄÉÃᩩßb¡⏚ឋÊàឋcḮâVgU¨ãV14ஹᶍ15ஹfᓱåUÏᣵrçSᑖèᡂéSRS¿N/ᔠXoᡂê╆□X16ஹrN=efGíE6ᾦ]NḄឋîឋᯠÊ@¨nðSñḄN=ᵫgᐳòᦔÃᐸឋḄ¯°ᵯôᑖᦣ¼½¾ឋᡈὅíE⏒ùឋú¡஺