大学有机化学习题集习题集

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ᑡᓄᔠᱥᵨ஺•234CH3cH—CH—CH-CH—CH—CH223পCHCH5CH-CH3332,3,5-ᵬ-4-6CH27cH31234567CHCH-CH—CH-CH—CH—CH3223ফCHCHCH-CH2,3-ᵬ-4-333CH3123456বCHCH-CH—CH-CH—CH3232,3,5-ᵬCHCHCH3332ஹᑡᓄᔠᱥḄᔲ᝞ᨵ┯ᦋ஺CH3CHCH9CH3পI2-X3-ᵬc2H5CH3ফCHCHCHCHCH2,3-ᵬV323CH3CH3cH2cH2cHeH2cH2cH3বCHCH4-J3CH3CH3CHCH2CH-CHCH2cH3ভAuu44,6-ᵬ-x2,4-ᵬCH3CH3CH2cH3CH3cH2cH2cHeH2cH3মCHCH3-x2-ᵬ-3-3CH3CH3cH2cH2cHCH2cHCH2cH2cH3(6)II.6-4X4-6uC2H5CH2cH2cH3

13ஹᑡᓄᔠᱥCH2cH3I51CH3cHeH2cHeH2cH33-ᵬ-5-CH2cH2cH3678CHCHCHI2I33l43567l832CH3——CH—CCH2cH2cH2CCH32,3,3,7,7-ᵬCHCH3312345CHCH-CHCH2cHeH2cH33বCHCHCHOiCH2,3,7-ᵬ-5-3323CH3CHCH312345163789I4CH3cHeH2cH-CCH2CH2CH2CHCHCH32,4,5,5,9,10-ᵬH-CHCHCHCH33334ஹᑡᔜᓄᔠᱥCH3ফt^CH3CH3CH3Lᵬ2-3-1,1,2,3-!ᵬ"2-ᵬ-3-

26-ᵬ#3.2.0
8-ᵬ#3.2.1
8-ᵬ#4.3.0
(11)6-ᵬ$3.5
1,3,7-ᵬ$4.4
1-ᵬ-7-$4.5
᷾5ஹ/0123C24C3Ḅ5678ᑏ:;<ᐺ>Ḅ᪀@AB᝞CC2DC3EFG67BH3GDC2EFḄ஺567IB8ᑏ:J<ᐺ>᪀@AKNewmanᢗMA⊤O஺&'()ᑏ+2,ᐺ.᪀01'2314516ஹ᪀⌼D᪀@ᨵQGRᑨTᑡᔜUᓄᔠᱥ᪀⌼V᪀ஹ᪀@V᪀BWXᐰZRḄᓄᔠᱥ஺&'᪀⌼᪀77ᑖ9:;9ᡈ;9=Ḅ᣸ᑡABCDEF7,᪀⌼GHᡂJ7,᪀⌼KLMNᓄPQ஺᪀0᪀77ᑖ9:;9ᡈ;9=Ḅ᣸ᑡABSDTUᵫWC-CᓫQYᵫZGᡠ\]Ḅ;9ᡈ;9=ḄS^_`CDEF7,᪀0GHᡂJ7,᪀0C◤⌕MNᓄPQ஺᪀0᪀cde▭ghD7ᓄᔠᱥkD7ᓄᔠᱥd᪀0lSDk

37ஹᑏ:ᑡᓄᔠᱥᨬ\]Ḅ᪀@A஺(1)(p)ফব8ஹ^_ᑡᔜ`ᓄᔠᱥḄabcdBefgᳮᵫ஺(1)"&'b.p:"ு(stuvwḄxTSyz{v|)(2)"2,2,3,3-!ᵬ&'b.p:"2,2,3,3-!ᵬ(stuvwḄxTSyz{v|)(3)ஹ2-ᵬ3,3-ᵬ&'b.p:2-ᵬ3,3-ᵬ(stuvwḄTSyz{v|)9ஹ^_ᑡᔜ`ᓄᔠᱥḄᰚbcdBefgᳮᵫ஺(1)"ஹ}&'m.p:}~"ு(ᑖ9Ḅ^ឋvTᨔvᜧTᰚ{v)(2)"2,2,3,3-!ᵬ&'m.p:2,2,3,3-!ᵬு"(ᑖ9Ḅ^ឋvTᨔvᜧTᰚ{v)10ஹᑏᡂᔜlmAI(1)—CH+HI——►(CH—CH—CH-CH)3323OSOOH2(2)|^>-CH.2_1A(CH3cH2cHeH3+CH3cH=CHCH3+3⌕ᱥ⌕ᱥ

4cᓄP1ஹᑡᓄᔠᱥᨵ^☢ᡈ^:?CHCOOH3H33CবHOOCCH3ᨵ^☢dokᨵ^9kᨵ^:dik2ஹᢣ+ᑡᑖ9Ḅ᪀.RᡈSCHOBrIIH(1)HO—j—H(3)CH-J—COOH3(2)CH,—D(4)CH-CH253CH2OHHNH2NH2(S)-(S)-(S)-(R)-3ஹᑡAஹBஹCஹD!,ᓄᔠᱥᙠ,hᨵZᐝឋḄ?CHCHCH3CH333HOᓝHH——OHHᓝOHHOᓝHH^—OHHO——HH—[-OHHO/HCHCHCHCH3333(A)(B)(C)(D)(1)(A)ᓫᙠYes(2)(B)ᓫᙠYes(3)(C)ᓫᙠNo(4)(A)(B)ḄᔠᱥNo(5)(A)(C)ḄᔠᱥYes(6)(A)(B)ḄCᔠᱥYes

54ஹᵨR,S-¢£¤¢£⏀¦⏚Ḅ,᪀c஺('00H(OOH(OOHH—1—OHH]¨OHHO-SOHHO-^¨HH3¨OH(OOH(OOH(OOH(A)(B)(C)(2R,3S)-2,3-nop1n⏚(2R,3R>2,3-nop1n⏚(2S3S)-2,3-nop1n⏚5ஹ1,3-ᵬᨵAp᪀c^᧜cª«ᨵT¬ᑏ+஺aICH3&'ᨵ஺A-1,3-ᵬp-1,3-ᵬ^᧜᪀ᨵ^᧜᪀!®1ஹᵨ¯°ᱥ¢£¤ᡈ±²¢£¤¢£ᑡᔜᓄᔠᱥ(1)(CH)CHCH=CHCH(CH)^®or2,5-ᵬ-3-®323212345678(2)(CH)CHCHCH=CHCHCHCH2,6ᵬ4®32223CH3¹3ºCH3(3)|^S-CH2,3-ᵬ®(4)5,6-ᵬ-1,3-®32ஹᵨZ,E-¢£¤¢£ᑡᔜᓄᔠᱥC

6CH/CH2cH2cH33X(4)I/C=Cஹf(E)-3--2-®HCH(CH)323ஹXᡂᑡlmABr(3)(CH)C=CHCHÃᘤᱥA((CH)CH-CHCH)3233234ஹᑡᔜ`ᓄᔠᱥᑖs4tuvwᡂlmBᢣ:y`z{|}lm_~஺পCFCH=CHCH3cH=CH2,ফCH3cHÆÇ,(CH)NCH=CH32332(3)CH2=CHC1CH=CH9^y//ভCHC1=CHC1CH,=CHC1'X'//2&'®É¿ḄÊᡂpyhᵫËᵯÍᑺ✌ᐜÑÒE#Qgᵯ9ÓÔÕvᜧTvᨵᑭWËᵯÊᡂpyḄÑ×஺ᡠ)TᔜØ:pyÙÚὅ᝞gᡠÝ஺5ஹᑡlmḄᱥlmᳮᡂḄᑏ:ᐸlmᳮ஺CH,CHCHBr33IHBrII'ICH=CH-C-CH►CH—CH-C-CH+CH—CH-C-CH233333CHBrCHCH333&:

7CHCHCH333III+C-八+HC--ᵬßàCH-CIIICHCHC33dâã"ä9kdâã"ä9kCH3CHBrI3CHCIICH—CH-C-CH33BrCH3CH36.XᡂᑡlmA:BrOH(CH)C=CH-1ீᓃ322CH—C—CHOH+CH—C—CHBr3232(1)CH3CH3wçফ&è:(CH)C——CHH6A(1)F!3222\+/Brফব(1)HSO24d4k------------>OHফH0O2CH80%HSO-HOম◊=242THF(CH)CCH—CHOHয(CH)CCHCH—-332233=2HCHCH33(1)1/2(BH3)2(7)AC2H5CH-CH2OHCHC=CH(2)HQ,,OH-,H,0252

87ஹXᡂᑡlmACH(CH)CH=CH-CHmHa(CH(CH)CH—CH(3)32923292O/\)(CH3)2C=CCH2CH=CH2..ಗmQRCO.3HA(4(CH)C——CCHCH=CH3222CHCI3,CCH3CH3ìᓄpyíhî°ᙠᵯ9ÓÔÕÙᜧḄ#Qg஺CH3fH3KMnO,OH-4(5)I----------------ACH3CHCH—CH2CHCHCH=CHHO,O°C322OHOHOHOHKMnO,OH-4II(6)CH3cH=CHC3H7H0,0°CCHCH—CHC3H7238ஹᑏ:ᑡlmᱥḄ᪀⌼A(1)C8H—A)প"Q-H*°HTòa(CHB'CHCH2cO2H+CHCHCOH322ফH+CH3(A)Ḅ᪀⌼ACHCHCH2CH=CHCHCH323

9(l)KMnO4,H2O,OH,A|'JHio(B)G►CH3cH2c=0+C0+H022CH3(B)Ḅ᪀⌼ACHCHC=CH322(l)KMnO4TH2O,OH-7tli2(஺)CH3cHe02H+CH3cH2co2H(2)H+CH3(C)Ḅ᪀⌼ACHCHC=CCHCH3239ஹG⛳DᑖsᑮᑡᓄᔠᱥBK¡ᩭG⛳D£Ḅ¤᪀஺(1)03(1)CHCH,CHO+CH3cHO"ö7CHCHCH=CHCH3(2)H2O,Zn323প஺3C2H5cHeHO+HCHO-<-------------C2H5cHeH=CH,(2)2'I(2)HO,Zn--I2CHCH33CHপ஺33I(3)CH3CH0+CH3CCH2co2H+CHCOH<-CHCH=CCHCHCCH32(2)HC>323o10ஹXᡂᑡlmAপCHCH=CHCH+Cl(CHCH=CHCHCI+CHCHCH=CH)3323232ClBr(2)C2H5cH=CH2NBSCHCHCH=CH+CHCH=CHCHBrBPO323211ஹ3-¥-1,2-n¦§28¨ᩔ᪷᷈¬Ḅ®¯BK⌱±〉³Ḅ¡ᧇᔠᡂE஺&.CH2=CHCH3µ¶CH2=CHCH2clb-CH-CH-CHCI224BrBrᯋx1ஹᵨ·ᱥᡈᑡᔜᓄᔠᱥ123456d1kCH3cH2cCCH2cH3ᯋor3-ᯋ

105432τফCHCHC(CH)CHCH3,3-ᵬ-1-Ú323212345বCH2=CHCH2c¹CH1-®-4-ᙽCH2cH2cH3654321(4)HC=C-C=C-CH=CH3,4--1,3-®-5-Ú2CH2cH2cH32ஹXᡂᑡlmAHHlindlarÿᓄᑺஹc=cপC3H7c¹CC3H7----------------->C3H7/ஹc3H7C3H7c¹CC3H7Li'»H3AH\/C3H7ফCH/C=%3HOOCBrবHOOC—CHC—COOH+Brc=<2B/ஹCOOH(4)CH=CHCHCECH►(CH—CHCHCECH)2232Br(5)HBr/I\CH(CH)C=CH——►CH(CH)3—C=CH3233222HBr/(6)CH3c¹CH^^(CH3—CH2—CHB¼2ûপ1/2(BH3)2/CH(CH)2/CH2cH332XCH(CH)CHCCHü32225(2)CH3cO,H,0°C/C=Cஹ\HHvjnrIý(k4H9cH=CHAC4H9cH2—CHO

11ooKMnO,HOIIII(10)CH3cH2cCCH342CH3CH7C—CCHpH=73KMnO,H,O/ஹ4(11)HC=CCH3pH”(82+H2O+CH3COO-)3ஹᑏ:½ᯋ4¿᪶Kᑺ(CN\HCN)wᡂḄlmᳮ஺JJPMCH=CH+CN--►CH=CHCN%CH2=CHCN4ஹᙠC2H5஺ḄÃᓄ,CH3c¹CH4C2H50Hlm,ᱥCH=C(CH)OCH2325ÄGCH3cH=CHOC2H5,᪶ᡂCH--CHCH+c2H5O--►CH-C=CH-c2H5஺1CH3—C=CH2338+6xr1IINuclearreagent࠷2H5OCH255ஹᵫ§ᯋÅÆ⌕ḄḄ¡ᧇᔠᡂ2-È~஺Na,NH(I)„„-CH(CH)Br3rrMo323CH3cCH-------------►CHC=CNa___-_►CHCHC(CH)CH332336ஹÉᔠᡂ2,2-nᵬp-3-ËᯋB◀ᵨÍpÎDÏÍ᜜BÑᨵJ<¡ᧇ8Ò⌱±BÓÔ⌱±¡ᧇDÕ¬ᔠᡂ_ᔠᳮ(1)CH3cH2cCHv(2)(CH)CCHCH43)CHCHBr(4)(CH)CBr333233⌱5(2)(CH3)3CCCH6(3)CH3cHzBᴂ89ᔠᳮ஺NaNHCH.CHBr22(CH3)3CCCHA(CH3)3CCCNa—(CH3)3CCC—CH2cH3>NH3᝞@⌱5পCH3cH2cCH6()(CH)CBr,AB⌕DᑮF◀Hᱥ433(CH)C=CH322O7ஹXᡂᑡlmA(1)CH3cH2cCNa+HOߟ►(CH3cH2cCH+NaOH)2(l)NaNH2,JNH3(2)(CH3)3C-C=CH(CH3)3C-C=C-CH3ফCHI3

12বC=CLi+CH3cH2cH2BrCC-CH2cH2cH3CHCH33(4)CH3cHeH2cCHব1)R"CHCHCHC=C-(CH)CH(Z)Crl3(vri2)3d\32233/,8ஹLA1-MN63-MOḄQᔠᱥᑖSᡂᔜUḄVW஺CH(CH)CHCH>Ag(NH3)2+fCH3(CH2)3CCAg
ஹZ[323>--------►<>-----►C2H5cCC2H5JெXJaHNO.3r[b------►CH(CH)CHCH323Jெ[J-----►C2H5cCC2H59ஹcᑡᔜeᓄᔠᱥᡈghSiᡈUᵫklmnopq9rsq(1)3-ᵬk-2,5-uvw65-ᵬk-2,4-uvwJHH.CH3cH=CCH2cH=CHCH3CH3cH=CHCH=CCH2cH3xᐔᐔᐳ{ᨵᐔᐔᐳ+++(2)(CH)C=CHCHஹCHCH=CHCH6CH=CHCH3223222+++opឋ(CH3)2C=CHCH2>CHCH=CHCH>CH=CHCH32226mo-H~ᐳ{3mo-H~ᐳ0m5H~ᐳবX/(CH3)2CHCHCH=CH2ஹ(CH)2CCHCH=CH26(CH)2CCHCH32323opឋ(CH3)2CH1HCH=CH2>(CH3)2&H2cH3>(CH)CCHCH=CH3222ᨵp-nᐳ{xP-ᐔᐳxPfᐳ1_________________________Jஹ/ᵯiឋ:-CH>-CH=CH32+++(4)CHCH=CHCH=CHஹCH2cH=CHCH2cH36CH3cHeH2cH=CH222

13ᓝ+opឋCH2CH=CHCH=CH2>CH2CH=CHCH2CH3>CH3cHeH2cH=CH2ᨵᐔFᐳxᐔᐔᐳxᐔ-ᐔᐳᨵPᐔᐳᨵP-ᐔᐳxPFᐳV(5)CH,(CH)CHCH,CHCHCHCH6(CH)C332232333ᵬkUᵫkUᵫkvUᵫkUᵫk\Z.(CH2CH=CH)2CH,CH2=CHCH26CH3cH=CH5msp2ᩖᓄgᐳ3msp2ᩖᓄgᐳᡂᓫᵯiᙠP⍝,ᐳᜧᐳnᐳয10ஹᡂcᑡ¡¢ᳮᵫ஺oBrBr(1)CH2=CH—CH=CH,+B.v?C»|CH=CH—CH—CH\2?(¤¥c¦§¨Hᱥ9B⌕Hᱥᓽª1,2-ᡂ9B஺)CH0CHஹ33(2)CH=C-CH=CH+Br«3A(BrCH-C=CH-CHBr22222(n¬¥cª1,4-ᡂ9BᡂopḄ®§¨Hᱥ஺)“ஹn¬¥বCH=CH-CH=CH-CH=CH+Br-----------►222(BrCH—CH=CH—CH=CH—CHBr^22(n¬¥cᡂopḄ®§¨Hᱥ஺°1,6-ᡂḄHᱥᐳ¬op஺)11ஹLᑨ²cᑡḄ³@¡¢´µ஺(1)C1CH2=C—CH=CH2+HCl(lmol)---►CH-C=CH—CH+CH—C-CH=CH3232CHCHClCH333++o,pឋCH3-C-CH=CH2>CH2=C-CH-CH3CHCH33

141,2-wᡂCH3CH=CH—CH=CH2+HCl(lmol)ACH3-CH=CH-CH-CH2ClH\]ឋCH—CH=CH-CH-CH>CH—CH-CH-CH=CH3332212ஹXᡂᑡlmACH3CH3CHO(1)CH=C-C=CH+CH=CH-CHO222C6H5—CH=CH—CH=CH—C6H5COOC2H5(2)+C2H5OOC—C¹C—COOC2H5COOC2H513ஹXᡂᑡlmA:

15¶·¸¹º»¼½¹¾1ஹᑡᔜᓄᔠᱥᡈpÚ:HCCH3X3ac=cHCH(CH)23Ü2Ûp21Ý1-ᵬp-2-½p-4-V§pÛ(E)-2-Ûp-2-1Ý(CH)C-CHC(CH)3333CH2cH2—B-Û½p2,6-nᵬpÛp2-Û½p2,2,4,4-;ᵬp-3-ÛpÞ22ஹᑏ:ᑡᔜᓄᔠᱥᡈpḄ¤᪀A:_/Cßপ¿À½^-CHCH2(2)Áᵬ½kÂÃÄCH3

16PhஹHব(E)-1,2-v½ÇwேC=CHPh\-CH.CH2cHeH2cH32(4)É-5-ᵬk-1-½k2uw'~/C=C/XCH3HH(5)v½ᵬkC6H5-CH-C6H5য3-½k2ÍwkCH2-CH=CH-C6H53ஹᑏ:½Û4ᑡKᑺ¨ᵨḄlmAàáᑁÃᓄᑺ:(l)Cl(FeCl)(2)Q⏚(3)hÀ⏣(BF3)23(4)Íw(xÑA1C13)(5)Í⏚⏊(CH3cH2co”0(xÑAlCb)(6)Í⏒×CH3cH2coe1(xÑA1C1)3পmCH2P9CH2cH3CH2cH3CH,=CHCH3(4)——-----------^/kCH(CH)32xÑAlCbCH(CH)23CH2cH3qH2cH3gyCH2cH3(CH3cH2:8):2஺ম--------~►+xÑAICI3COCH2cH3O=CCH2cH3CHCHCH2CH323CH3cH2coeI0+OyCH2cH3(6)-------:------>xÑAlCbCOCH2cH3O=CCH2cH34ஹᵫÛDÆ⌕Ḅ¡ᧇᔠᡂᑡᓄᔠᱥ:পO-O

17(ᡈÂMw)Ü:+HO(2)ÝÀ½CHCH331H2sO4+CH=C-CH----C-CH3230CH3CH-(CH)-CH2253OHO-gZnH-HaCH(CH)CH2253ooIIII(4)C-CHCH—C-OH225ஹLª½6⌕Ḅ´ᧇᔠᡂhͽ஺OO0)+CH3CH2C-CIA஺-Zn-HgCH2cH2cH33AOlC-CH2cH3HC1,or(CH2cH38)2஺6ஹᙠ×ᓄàḄáᙠc½6âÃk×ãᵨB⌕Hᱥ2-ᵬk2½kÀÄ,°âÃk½஺Låæ஺ᑏèéᳮ஺CHCH3+3CH3—C—CH2c+opឋCH—C-CH—CH>>323CH3ghSighSiCHCHI3^^^AIC1I3■H3CH—C—CH—Cl--------►CH—C—CH—CH323234-CHC(CH3)2CH2cH33

18CH3r^>]—C-CHCH237ஹᑏ:å¥ᓄÛᨬ\]Ḅ᪀@A஺êᳮë¡ì×ᓄ½ᨬopḄ᪀ï8ஹᑏ:ᑡlmḄᱥᡈlmᱥḄ᪀⌼A:

19æ9ஹᑏ:ᑡᓄᔠᱥ|¦ᓄḄç⌕ᱥ஺10ஹXᡂᑡlmA:11ஹᵫÛÅÆ⌕Ḅ¡ᧇᔠᡂᑡᓄᔠᱥ:

20(1)CHCH23ফ*NO2বBrফ12ஹªnðḄH᳛ᵫ½6xéLᑺᑴᜓ4-ôk-1,2-võ½஺NO2NO2

2113ஹᡂcᑡ:cocH65(1)AICI3+C6H5c—ClCS,A2A1C13C6H5NC)2JOCHবoi3xor”/\^^COOH14ஹᵨHuckelᑣᑨ²cᑡᓄᔠᱥஹSi6Uᵫkᔲᨵ¹✏ឋ?(2)A(3)xxx

22ভমV(6)-----+ᨵᨵx¶û¸ᓴýº1ஹᵨþÿ

ᑡᔜᓄᔠᱥᡈᑏ᪀஺(1)CH(2)Cl31CH3cHeHCH2cHeH3CH3CHCH2C—CHCH3CH3ClClClCH32,3-ᵬ-5-2-ᵬ-3,3,5-বBrCH2cH2cHeH2cH2cH3(4)CH3cH2cHeH2cH3C2H5CH2C13--1-3-ᵬ(5)(6)ClC^CH31-21•ᵬᡈB-CH^/CH33/\-CHCI21-!2.2.1
"11ᵬ2ᵬ(9)#$%1஺&%R-2-(CH3CH3CH3—CH-CH2CH2BrBr—LHCH2cH2cH3

232ஹ
ᑡᔜᓄᔠᱥ:পCl2cHeH=CH2ফCHCHCH=CHCH(3)33CHBr33,3--1-+,Cl4-2,1-ᵬ4(2,(4)(5)/=\Br6VCH=CHCH2CH2Br1-4(11-1-4-(-1••7,(6)2-4:,+1Brஹ8CH2cH=93-(2■•4<1)-1-+,C13ஹᑏᑡᔜᓄᔠᱥḄ᪀⌼ᡈ᪀:প4-(-1-7,3@ফD-1,2--1,2-1,CH2=CH—C=C—BrPh\EC=Cer'phবAB71(4)a-(F1CY2^C(CH3)34ஹG⚜IᑡᔜAᓄᔠᱥJKLMNOP஺QR(1)TỚுT(2)T7<ு#7X(3)T$ீT"((4)Zᵬ1ீZ(ᵬ15ஹGᵫᓴF]⏣_`⌕ḄbcGᑺᔠᡂᵬB7⏚[CH3—O-C(CH3)3](ᡠᵨiᧇk⌱)஺QR(CH)COH-^-►(CH)CONa(CH)C-O-CH33333336ஹGᵨᓄm␺oᑡᔜpᓄᔠᱥR(1)1-72.72-ᵬ2.+ফ1-1-:71-Ớ+

24CH3cH2cH2cH2஺ஹAgClJrstuvClCH3cH2cHe%JBïCH3cH2C=CHCH2cH3পII⏣ACH3BrCH3BrCH2cH2cH2cHeH3K°H/CH=CHCHCHCH\223ফCH⏣A[CH/33CH3CH3BrKOHব⏣A)

25CH3CHCH2BrZn(4)----->CHBr2BrBrKমCH3CHCH2CH2CHCH3+2NaOH(CHCH=CHCH=CHCH)33ClI⏨,\(6)CH3CCH2cH2cH3+2NaOHߟ(CH3cCCH2cH3)ClCH2=CHCHCHCH(CH)2CH=CHCH=CHCH(CH)2'i2I3C5(JH'93/BrClCl/CTTLTSTTETT\c2H5ONa(8)CH3cH2cH=CH2—iCH3cHeH=CH2ஹ1__Lߟ>CH=CHCH=CHR500C\/C,H50H22NaNH/ஹ2C6H5fHCH2Br᪗;(c6H5cCHBrZn/\(10)CH=CH—►CH=CH+ZnBr+HI22A\/9ஹᡂᑡDR⏒/ஹ(1)(CH)CC1+MgA<(CH)CMga3333\/(2)CH3cH2Mgi+CH3OH—►(CH3cH3+CH30MgI)ব+CHMgBr►(Qx"CH25+260/H\0/MgBr,ஹ⏚(4)C2H50cCH+RMgX-------►C2H50cCMgX10ஹᵨᑡᓄᔠᱥᔲᑴᜓGrignardGᑺ¤¥¦§¤(1)HOCHCHBr(2)HC=CCHCHBr2222CH?—C—CHzBrCH3cH2cHe&BrবK3(4)IOCH3

26QR(1)஺¨¥⏣©ªḄ«i¬¥®«ᑖQGrignardGᑺ஺(2)஺¨¥@«¯°®«ᑖQGrignardGᑺ஺(3)஺¨¥ᐸᑖ¬ª²ᨵ´GrignardGᑺrᡂ஺(4)஺¨¥ᓴi¬ḄB-Cµᨵᵬ¶·¸¹º◀D¹ᡂ,¼஺11ஹᡂᑡD12ஹᙠᑡᔜp¾᪶GᑺªJKL¾᪶ឋÁ¤(1)crffCHS-A/(2)CH3NH2]CHNH-yl(3)2°RX>3°RX(3)

27CH3cH2cH2cH2cH2Br+NaOH--aCH3cH2cH2cH2cH20H+NaBr஺SN21°RX,⌕ÉÊSN2D—Ë@!ÞZßàØáâ᝱äå஺9H3CH3IH0I2CHCHCHCHBr+NaOH---~CH3cH2cHeH20H+NaBr322SN21°RX⌕ÉÊSN2DKO᠒ÞZßàᜧáâ᝱äå஺14ஹᓴFNaOHᙠK⏣ÎçªÉÊDᑡJè°SN2cᳮ¤Jè°S1cᳮ¤Nপᱥ¸¹WaldenéᓄêS2N(2)ërÎᑺḄ²ìDíîr@êS1N(3)ᨵï᣸DêS1N(4)BᓴFDÜ᳛ᜧÐñᓴFêS1N(5)DòᨵKó஺S2N15ஹᢣᑡᔜADªÆὅO@஺পCHCH33CH3cH2cHeH,Br+CN------►CHCHCHCHCN+Br'(ÞZßàᜧ)322O᠒CH(CH)Br+CN'—►CH(CH)CN+Br'(ÞZßàØ)323323O@ফH2O(CH)CHCHCI—^ߟ►(CH)CHCHOHO᠒322322LøஹRr&O(ùúûRBr>Cl)(CH3)2CHCH2Hr---------a(CH3)2CHCH2OHO@AবH20CHI+NaOH—=—►CHOH+Nai33O᠒HoO(¾᪶ឋRSH">OH)CH3I+NaSH—CHSH+Nai3O@(4)CHI+(CH)NH--------ACHN(CH)+HBr(ÞZßàØ)332332ü@CHCH(ÞZßàᜧ)33CHI+(CHCH)NH…a(CHCH)NCH+HBr332323ü᠒(ᵬýḄpKb=3.27,#+ýḄpKb=3.2?)

2816ஹᑏᑡDḄcᳮ:(CH)C-CHCH2»(CH)C=C(CH)+(CH)C-CH(CH)33332323232ClClQ:cHCH—33+ZnC12|+CH3-þÿC-H-C—CH-CH—~~»-(CH)C-CHCH---^CH333-ZIICI330I-3I-3cHciCHC3+)(2°C+)(33°c(CH)2C=C(CH)233Cl-I-^C-l►(CH3)C-CH(CH)23217ஹᑡᓄᔠᱥᢥElᳮ◀HBrḄ᧕᣸ᑡᑏ⌕ᱥḄ᪀⌼#஺CHCH,3I-ICH3(1)CH-C-BrফCH3CH?HCH3(3)I3IICHsCHCH2m2&'CH2cH3Br()El*+,᳛)(1)>(2)>(3).CH3/0*+ᱥḄ⌕ᱥ12)3&I'&'&CH3—C=CHCri3ᐸ6(3)Ḅᱥ27᪵9ᡂḄ)_B.+H—;<CH3cHeH2cH2BrCH3cHeH2cH2------------►CHCCHCH323CH+3H+I---►CH—C=CHCH3318ஹ=⚜?ᑡᔜ*+Ḅ⌕ᱥAᓫCDᳮᵫ஺/CH\3প(CH3)3CBr+CN---------►LI'&(3°RX᧕◀)TT\CH2=C—CH3/(2)CH(CH)Br+CN-----------►(CH3cH2cH2cH2cH2CN)(1°RX᧕HI)324

29/CH,ஹ(3)(CH)CBr+CHONa--------►[I(3°RX᧕◀)3325\CH=C—CH)23CH3(4)(CHj)3C0Na+C2H5cl►(CH3—C—O—CH2cH3)(VRX᧕HI)CH3CH3cH2cHeH3+HS-——►/CH3cH2cHe/\(5)''II'I(HSḄJ᪶ឋMNឋO)Br\SH/(6)CH3cH2cH2Br+CHQ->CHCHCH-O-CHj(f>RX᧕HI)3322319ஹPᡂᑡ*+#:20ஹRSᑡT⚪:প°NX2XN(CH3)2VKOHWXYZ[ᐳ]^ᨵ(CFhhNH`=T*+ḄaZᱥ2bcd(:aZᱥ2ON(2)ᑡᓄᔠᱥVC2HsONa*+ᢥᐸeឋᵫᜧᑮh᣸ᑡCDᳮᵫ஺NONONO222(A)O2N(B)CH-^>-CI(C)NC3()*+eឋ)A>C>Boij)ᔾᵯmឋNO?—>N/C—>CH3Z.noᵯmpqrstsᨵᑭvJ᪶HI*

30+Ḅwx஺(3)ᑡyzᓄᔠᱥᑖ|VC2H5(DNa*+Z0ᓴim᧕HIdbcdON^^Br2(A)(B)CH3()(B)ᑖm6Ḅim᧕HI஺jḄᔾᵯmᦔ+ᜧvᨵᑭvC2H5஺wVḄ஺21ஹXᡂᑡlmA:22ஹXᡂᑡlmA:

31Cu23ஹᑏᑡ*+Ḅᳮ(bc*+⍳ᑣ஺CH=CH-C1+HC1--------►CH—CH-C123Cl(CH^=CH^C1——ACH—CH—ClC1»3ឋ:CH—CH-CI>+CH—CH—Cl32224ஹPᡂᑡ*+#)পC1^Z^CH2C1CHOH2^\^CHC1(H/^\/CH2CH2C3)2NH+/3CH1\H3বC1CH=CHCHC1C$80aCICH=CHCH—OCCHj223ভ(CH)CCH=CHH20A(CH)CCH=CH+(CH)C=CHCH322322322Br¨OHOH25ஹᑡy0ᓄᔠᱥᑖ|wxW(*+Z0*+©ªdbcdCH—^^CHC1CH^^^^CHOH+HC13232ON^^-CHC1ON-^^>-CHOH+HC12222()¬ᵬ®¯°ḄW(*+©ª஺jC+ឋ)CH-^^>-CH2>ON^r-VcH322

3226ஹXᡂᑡlmAeᑏ:lmᳮ஺CH3cHeH=CH202H5OH/CHCHCH=CHCHCH=CHCH3232ISRτCl\OC2H5OC2H5ᳮ:CHCHCH=CHWCHCHCH=CH^-^CHCH=CHCH323232C!(1)(II)DC2H5GH.CHCHCH=CHH+CHCHCH=CH3232HOC2H5OC2H5C2H5OH»CHCH=CHCH.H+JCHCH=CHCH3232doc2H5OC2H527ஹXᡂᑡlmA:CH3NaOHপCH2=CHCHC(CH3)3CH2=CHC=C(CH3)2Br/—\³⏚(V-MgBr+BrCH2C=CH2——>Q^CH2C=CH2Q)BrBr28ஹᑏ:HC¹CCI^Br4MglmḄᨬôᱥBefgᳮᵫ஺HGCCH,MgBr:HC=CCH2Br+Mgߟ►HC=CCH2MgBr-ABrMgC=CCHMgBr+HC=CCH—H222H.ecH?BrAHCHCCH—CHCCH—CHCHCH222µ¶·⏣ஹ¹ஹ⏚1ஹᵨᑡᔜᓄᔠᱥBᡈᑏ:¤᪀A஺পফC1ICH3cHeHCH2cHe^CH3CHCH2C—CHCH3CH3ClClClCH32,3-nᵬp-5-¥Ë22-ᵬp-3,3,5-¹¥Ë2

33º3»BrCH2cH2cHeH2cH2cH3º4»CH3cH2cHCH2cH3C2H5CH2C13-½p-1-tË23-¥ᵬpÞ2মOO^H31-õÞp2¥½21-ᵬp-1-¥õË2ᡈ¥½põÞ2½CHCH33¶ᔆCH2cl1-¥÷õ2.2.1
È21,1-nᵬp2¥ᵬpõÞ2øVÞpùº1஺ºR2tÞ2CH3CH3CH—CH-CHCWBrBrfH32ü2cH2cH32ஹᑡᔜᓄᔠᱥপC1CHCH=CHফCHCHCH=CHCHব2233CH3Br3,3-n¥-1-§Ýci\=14-¥2ÞÝiᳮp4ù2õÞÝ5/=\cl^CrBrúy-CH=CHCH2CH2Br1-¥4tÛ1-Û4¦1.1Ý6/=\BrúûCH2cH=ºd2■¥4tݧpÛ3-2■¥4.tÛp-1.§ÝCl

343ஹᑏᑡᔜᓄᔠᱥḄ᪀⌼#ᡈ¿᪀#:ফ4-Á-1-ÂÃ-3-ᯋফ*-1,2-¯-1,2-nÈÃCH2=CH—C=C—BrPh\Ë/C£crphব¬¯ÅÂn(4)a-ÁIÈnC௃Y2^C(CH3)3(^CHCH3Br4ஹ=⚜?ᑡᔜ¬ᓄᔠᱥZ0ÏЩÑ஺()(1)ÒÓ®ỚுÒÖ®¯(2)Ò®×>Ø®(3)ÒÖ®Ù(ÒÚ®Á(4)Û¯ᵬnீÛᵬn5ஹᢣᑡᔜÞᓄᔠᱥZ0Ꮤ᩽á©ᜧ஺()(1)CH3cH2C1>CH3cH2Br>CH3cH21ddâ(2)CHBr------3A4AgClJ`ûᱏýö÷ø()পC1⏣1CH3—c—CH3,

35CH3cH2cH2cH2cH2clஹ'NaClJºÿ
NaiফCH3cH2cH2cH2BrNaBrᐜ
CH3cH2cH2Iஹ
8ஹᑏᑖᑡᑺḄ⌕!ᱥ:$l°RXQORX%KOH/H2O(CH)CHCHOHOH322OC2H5ONa/&⏣(CH3)2CHCH20c2H5⌕!ᱥ!*AgBr1+^-ONOAgNC3/&⏣AgBr1+(CH)2CHCHONO2232NaCN/,-&⏣(CH)CHCHCNCN322O^FSCH3NaSCH(CH3)CHCHSCH33226NaU45(CH)CHCHI3229ஹᑏᑡḄ⌕!ᱥ8KOHপCH3cH2CH—CHCH2cH3--►/CHCHC=CHCHCH3223CHBr&ᓃ;\CH33BrCH2cH2cH2cHeH3K°H%/CH=CHCHCHCH\223ফCH&⏣>;[AH>CFI3\Crl3/(4)CH3CHCHCHCHCH+2NaOHA(CHCH=CHCH=CHCH22333Cl(5)CHCCHCHCH+2NaOH&∅*(CH3cCCCH2cH3)3223ClCH=CHCHCHCH(CH)2CH=CHCH=CHCH(CH)2I(6)22323Br

36CQl(CH3±HCH=CH2
DC2H5E/ÿ2aCH=CHCH=CH^iCH3cH2cH=CH222500CC2H50HNaNH22/\C6H5CHCH2Br»C6H5cCCH(8)FNHூ31)BrZnCH=CH+ZnBr+H)(9)CH=CHP2210ஹ
ᡂᑡ:H⏚/প(CHMQ+Mg…((CHRCMgQ(2)CH3cH2Mgi+CHOHߟ►(CH3cH3+CH30MgI)3Hব+C2H5MgBrc2H6H(4)C2H50cCCH+(RMgX)aC2H50cCCMgX11ஹᵨᑡᓄᔠᱥᔲᑴᜓGrignardᑺ(1)HOCHCHBr(2)HCCCCH2cH2Br22CH3—C—CH2BrCH3CH,CHCH2BrবভτOOCH3L8(1)M஺OP⏣QRḄSTUPVWS>MᑖLGrignardᑺ஺(2)M஺OPXSYZVWS>MᑖLGrignardᑺ஺(4)M஺OPᐸᑖUR\ᨵ^>MGrignardᑺ_ᡂ஺(4)M஺OPᓴTUḄB-Cbcᨵᵬe>fghi◀>hᡂkl஺12ஹ
ᡂᑡ(1)CHCHBr+2Li——►8CHCHLi+LiBr3232(2)CH(CH)C=CH_CH3(CHᔳnCH(CH)C^CLi+CH(CH)—H323323323

3713ஹoᡂᑡp0HপqrsCH3ߟ►CH3/^>CH33BrHNa!^^^^CH—BrH2°»(C^>Bf(2)22H>ஹH14ஹᙠᑡᔜvw᪶ᑺR>y%zw᪶ឋ|}(1)C~CH3S7(2)CH3NH2CHNH-(3)40HF3(4)THS%H2s(5)HO-HSW(6)NHSO'HSO'3415ஹ☢ᡠᑡḄw᪶>ᔜᢥᳮ}y%zX}P}S1N(CH)CBr+HO——►(CH)COH+HBr33233ஹ'4»3°RX,“᩽ឋᑺ>-----X!⌕S/ᨵᑭSNICH3⌕ZSN1I13CH3cH2cHBr+HO——►CH3cH2cHOH+HBr2''4»2°RX,*᩽ឋᑺ>%᠒SNISN2ᨵᑭSRফCH3cH2cl+Naiᑁ5aCH3cH2I+NaCl——XSN245(CH)CHC1+Nai■>(CH)CHI+NaCl3232SN2IḄ᪶ឋ!"#$%&᩽ឋ()஺+,ᩩ.ᨵᑭ1SN2஺SN22᳛1°RX>2°RX>3°RX(3)CH3cH2cH2CH,CH,Br+NaOH%°»a^CH,CH7cH>CH20H+NaBr%S2oN1RXl⌕SN2—X*¡¢£¤¥>¦§᝱©ª஺

38CH3CH3HOI2CH3CH2CHCH2Br+NaOH-aCH3cHoCHCHQH+NaBr1°RX,⌕SN2᠒*¡¢£¤ᜧ>¦§᝱©ª஺16ஹᓴNaOHᙠ,%&⏣FR>ᑡy¬ZSN2ᳮ}y¬ZS1ᳮ}Nপ!ᱥghWaldenᓄ¯S2N(6)°_ᑺḄ\,±²³_X¯S1N(7)ᨵ´᣸¯S1N(8)¶ᓴ·᳛ᜧ¹ᓴ¯S1N(9)ºᨵ%»஺S2N17ஹᢣᑡᔜR>ὅX஺(1)CH3CH3CHCHCHCHBr+CN'——►CHCHCHCHCN+Br'(¡¢£¤ᜧ)322322᠒CH(CH)Br+CN'——►CH(CH)CN+Br-323323(¡¢£¤¥)X(2)HQ(CH)CHCHC1—^ߟ►(CH)CHCHOH᠒322322H2O(¾¿MÀ8Br>CI)(CH3)2CHCH2Br—(CH3)2CHCH2OHXAHOCHI+NaOH—2—CHOH+Nai33᠒HQ(w᪶ឋ8SH->OH)CHI+NaSH--------aCH3SH+Nai3X(4)CHI+(CH)NH---------ACHN(CH)2+HBr(¡¢£¤¥)33233ÁX%(¡¢£¤ᜧ)CHCH33CHI+(CHCH)NH---------►(CHCH)NCH+HBr332323Á᠒(ÂᵬÃḄpKb=3.27,Â4ÃḄpKb=3.2?)

3918ஹᑏᑡḄᳮ8ZnCl,(CH)C-CHCH——(CH)C=C(CH)+(CH)C-CH(CH)33332323232ClClL8CHCH33ZnClr+CH3-ÇÈ+I'2(CH)C-CHCH--^CH-C—CH-CH————►CH—C-CH-CH333-ZnC133I33I3ciCHCH33(2°C+)(3°C+)!;(CH3)2C=C(CH3)21I1LCI_^(CH)C-CH(CH)323219ஹËᑡᓄᔠᱥᢥElᳮi◀HBrḄÍ᧕ÏÐ᣸ᑡ>Ñᑏ⌕!ᱥḄ᪀⌼p஺CHCHI3I3CH3(1)CH3—C-Br(2)CH3CHCHCH3বτCHCHCHCHBr322CH2cH3BrL8El·᳛8(1)>(2)>(3)¯CH3CzᱥḄ⌕!ᱥÖZ:CH—C=CHCH33ᐸR(3)Ḅ!ᱥZ×᪵ÙᡂḄ:C|H3--Br-C1Ha3H—ÇÈCH3CH3cHeH2cH2Br--------►CHCHCHCH-------►CH3CCH2cH3322CH3H+-_►CH—C=CHCH3320ஹ⚜ÞᑡᔜḄ⌕!ᱥ>Ñßᓫá²ᳮᵫ஺—(CHXCH(1)(CH)CBr+CN3(3°RX᧕i◀)33(2)CH(CH)Br+CN'ACH3cH2cH2cH2cH2CN(~RX᧕)324

40/CH,ஹ(3)(CH)CBr+CHONa--------►[I(3°RX᧕i◀)3325\CH=C—CH)23CH3(4)(CHj)3C0Na+C2H5cl►(CH3—C—O—CH2cH3)(VRX᧕)CH3CH3cH2cHeH3+HS-——►/CH3cH2cHe/\(5)''II'I(HSḄw᪶ឋ|>ãឋä)Br\SH/(6)CH3cH2cH2Br+CHQ->CHCHCH-O-CHj(f>RX᧕)3322321ஹ
ᡂᑡ:22ஹEFᑡG⚪:প°NX2XN(CH3)2KOH,F%åᐳç>ᨵ(CFhhNHè>éḄê%!ᱥZ}L:ê%!ᱥZON(2)ᑡᓄᔠᱥC2HsONa>ᢥᐸVឋᵫᜧᑮ¥᣸ᑡ>Ñá²ᳮᵫ஺NONONO222(A)O2N(B)CH-^>-CI(C)NC3L8Vឋ8A>C>BoTO8ᔾᵯUឋN02—>NCC—>CH3%¯îᵯUïðñòó>òᨵᑭw᪶

41Ḅ஺(3)ᑡôᓄᔠᱥᑖC2H5(DNa>y%zᓴTU÷᧕ø}P}ON^^Br2(A)(B)CH3L8(B)ᑖURḄùTU÷᧕ø஺OPùḄᔾᵯUúûᦔᜧý>ᨵᑭC2H5஺þÿ
Ḅ஺23ஹ
ᡂᑡ:24ஹ
ᡂᑡ:

42Cu25ஹᑏᑡḄᳮ⍳ᑣ஺CH=CH-C1+HC1--------►CH—CH-C123ClCH^=CH^C1——ACH—CH—ClC1»3ឋ:CH—CH-CI>+CH—CH—Cl32226ஹ&ᡂᑡ()পC1^Z^CH2C1CHOH2^\^CHC1(H/^\/CH2CH2C3)2NH+/3CH1\H3বC1CH=CHCHC1C$80aCICH=CHCH—OCCHj223ভ(CH)CCH=CHH20A(CH)CCH=CH+(CH)C=CHCH322322322Br6OHOH27ஹᑡ78ᓄᔠᱥᑖ=>?@AB8CDEECH—^^CHC1CH^^^^CHOH+HC13232ON^^-CHC1ON-^^>-CHOH+HC12222)HᵬJKLḄ@CD஺MC+ឋ)CH-^^>-CH2>ON^r-VcH322

4328ஹ
ᡂᑡPᑏRSᳮ஺CH3cHeH=CH202H5OH/CHCHCH=CHCHCH=CHCH3232ISRτCl\OC2H5OC2H5ᳮ:CHCHCH=CHWCHCHCH=CH^-^CHCH=CHCH323232C!(1)(II)DC2H5GH.CHCHCH=CHH+CHCHCH=CH3232HOC2H5OC2H5(II)C2H50HACHCH=CHCH.H+JCHCH=CHCH3232+1AHOC2H5OC2H529ஹ
ᡂᑡCH3NaOH,I(1)CH=CHCHC(CH)3ACH=CHC=C(CH)23232L2H5UH,"/—\P⏚(V-MgBr+BrCH2C=CH2——>Q^CH2C=CH2ফBrBr30ஹVWᑡᓄᔠᱥᡈᑏRY᪀:)(I)C2H50cH=CHCH2cH3(2)CH30cH2cH20cH3RJ-1-STJ⏚RU⏣UᵬW(3)CH=CHCHOC=CH(4)C1CH2cH20cH2cH2cl22TYJRᙽJ⏚B,B'-UKRWor2,2-UKRWOCH3(6)330cH3মLXCH(CH)322-ᵬ_J`a2,6-UᵬJ-4-cYJ`ᵬW(7)3-ᵬ_Jef(8)12h_Yf

44CH3cH3cHeH2cH2cH3H2cqeH-CH3OCH30(9)RU⏣BᵬW(10)-1,3-Uᵬ_JhifHOCH2cH20cH3CH3O....OCH331ஹ⌱^(_Ḅ`aᔠᡂᑡᓄᔠᱥ(1)jS⏚H3Po4orH2so4)2cH3cH>CH,CH20H--------=~►(CH3cHzCHoCH2%஺+HO2A(2)RJcYJ⏚)(CH)CH-ONa+CHBr——►(O^CHOC2H5+NaBr3225(3)RJkSJl)(CH)CONa+CHCHBr——a(CH)C-O-CHCH333323321.H,SC)4rᡈὅ)(CH3)2C=CH2+CH3cH20H—Boa(CH)C—O—CHCH3323(4)2,6-UᵬJ-4ஹpJU`⏚32ஹ
ᡂᑡ:CH3OH,H+----------------------------------------►CH3cHeH20HOCH3CH30H,CHONa3CH3CHCH2OCH3)-----------------------------------------►OH'NHCH-CH—CH332CH3cHeH2NH2\0OH'(l)CHBrMg;(2)H0252------------------------------>CH3cHeH2cH2cH3OH(1)CH=CNa;(2)H02CH3fHeH2cqCH)---------------------------------AOH

4533ஹᵨbcᧇᔠᡂefgbe⏣eᵬj(gᵞ⏣feᵬ⏒)஺:CH=CH+o222HoCH—CHVV222IIHO(CH2cH2O)2CH2cH20HOHOHOHOH-OH-2(CH3)2SC)XCH3(D(CH,CH2O)2CH2cH20cH3OH-34ஹᑏRᑡḄmᱥ:(1)CH3cH2cH2cH20cH3+(1mol)HI—►(CHI+CH3cH2cH2cH20H)3(S2)N+(lmol)HIa(HOCH2cH2cH2cH2fH(CH3%)ফ(SN1)IOCHo25CH—CH=CH—CH+HO^CH-C-CH-CH+C2H5OH)332323<^OCH2cH=CHCH3'I^V°H)f(4)U\^-CHCH=CH2ICH3rᓝt?vw1ஹVWᑡᓄᔠᱥ:(I)HOCH2cH2cHO(2)CHCHBrCOCHBrCH33

463-xJYW2,4-U|-3-iw(3)CH3COCH=CHCOCH3(4)3-eT-2,5-Uw4-ᵬJhew(6)CHO^2XC-CH(5)Br^2XCH033O4-y`ᵬWHᵬ_J`Rw(7){-kY^CH஺HO—CHO(8)00cH34-R⏒J`ᵬW4-xJ-3-ᵬ_J`ᵬWheJ`Jᵬw2ஹᑏᑡᓄᔠᱥḄ᪀⌼(:(1)ᵬJcSJw(2)SUWOIIIIIICH3CCH2CH(CH3)2H-C-CH2CH2C-HবqᵬJRWভheUw(CH)CCHO33(5)B-xJSW(6)HxJ`YwCH3cHeH2cHO0H0~^-C-CH?-CH3OH3ஹ⌱ᔠ〉ḄᧇᩩᔠᡂᑡJᓄᔠᱥ)(1)2-ewHBrMg)CH(CH)OHB►CH(CH)BrḄether»CHCHCHCHMgBr3233233222OMgBrOHCHCHOIH0I32dryetherACH3cH2cH2cH2cHe%CH3cH2cH2cH2cHeoKCrOII927.BB-aCH3cH2cH2cH2CCH3ᡈὅ)

47HCqCNa+BrCH2cH2cH2cH3--------►HCqC—CH2cH2cH2cH3H02dil.H^,HgSO?CH3CCH2cH2cH2cH3(2)SW[(CH)CHO]A1,(CH)C=O32332)CH3cH2cH2cH20H-----;---------:----------------ACH3cH2cH2cHOCH5,A6ᡈὅ:CrC)3PyridineCH3cH2cH2cH20H-------------------►CH3cH2cH2cHoOHHQ/H+"o->180Cs஺3HCHOCrO+(CHCO)O332--------------------------A

48oCCH2cH2coOHOHoCo\AleToII/二CCH9CH2COOHeno4ஹ&ᡂᑡ:CHCH33

49COCICHO5ஹ
ᡂᑡ:(Cx))প2c2H50H+“2H5ooIIIIফo+HNNH-C-NHN-NHCNH,22বHOCH2cH2cH2cH2cHO——►ভ

506ஹ&ᡂᑡ:CH3পCH3coe+CHqCH——►ILUYUJCri2=C—Crl=CH2OMglCH3coe%I)CH=CH+CH3Mgi-aCHqCMgl—)-------*CH-C-CHCH3CH3oHI+le-CH?ᓟCqCHᡡCH?ᓟicH3CHCH33ONaNH3CH3coe%Iᡈὅ)CHHCH+Na-------►CHHCNa-:-------fCH—C—CHCH3CH3OHOH”ᡈᓽ04[,OIHIH3PO42ஹCH3—C—CqCH-----►CH—c—CH=CH——►CH=C—CH=CH-IP-2ᓄᑺ3|2A2I,2CHCHCH333

51oH2OCHCHCN227ஹᢣRᑡᓄᔠᱥt#uvwxyz{|Ḅ}jfᔠ஺1(2)HCHO3CHCHCHCHO(4)(CH)CCHO32233)3>?¡xW¢ᔠ஺8ஹᢣRᑡᓄᔠᱥt#uv~Ớ஺1£ICHCHO2CH3cH2cHO2CH3cH2cHe(4)^>-COCH3বOH)পஹ3ஹ4¤¥¦Ớ¨஺9ஹ
ᡂᑡ:CHCHCHO©1(CHCHCH=C-CHO3232(Mannichreaction)KOHভCHO+°H20,CH=ixW¢ᔠ£CH3CH3CHCOONaOHC\CHO+2(CHCO)O——3;---------►32AমNaOOCCH=CHCH=CHCOONa(Perkinreaction)10ஹᑡᓄᔠᱥuyz?(I)CH3coeH2cH3ফCHO

52CH3fHeHO)2ஹ3ஹ4ஹ6¤¥¦ª«஺Hஹ
ᡂᑡ:(1)CH3cH=CHCH2cH2cHO2A(CH3cH2cH2cH2cH2cH2OH)(C=CC=O¬᧕¯°᝞²³vImolH2´µ✌ᐜ¯°)NaBH/\4(2)CHCH=CHCHCHCHO-------►(CH3cH=CHCH2cH2cH2(DH)322(NaBH>LiAlFU¸³°¹Jº°´µ)4(3)CHCH=CHCHCHCHOP'LH(CH3cH2cH2cH2cH2cH2OH)322(Pdᓄ»ឋ¼½)(³vImol%¾´µ✌ᐜ¯°¿ÀÁ¾ôµvÄJž°)Ag(NH),OH/\3(4)CHCH=CHCHCHCHO--------------►(CHCH=CHCHCHCOOHj322322(ªÆǺ_ᓄ´µ)(5)CH3cH=CHCH2cH2cHO(CH3coOH+HOOCCHCHCOOH22ÈÉX(ÈḄKMnOÊÉÇ_ᓄ´µ)যQ/COCH2cH2COOH—ÌB-(2cH2cH2COOH(Clemmensen°)(Wolf-Kishner.ÍÎÏ°)(8)

53½ÔឋÑ᪶Öᑺ>×ØJ஺ÙÖᑺḄÔឋ¼½⍗»ÛÀᑖ!£´Tᔠᡂ஺Ñ´TÝÞᨵᔾᵯáJâ㾬ᨵᑭ஺£NaBH.UAIH4¸³°åJº°´µ஺MA1H)ḄÔឋ¼½³>×æJ•£400NaCN/||\5PhCH=CHCPh»PhCHCHCPhjHQAc2CNèÔឋÑ᪶Öᑺ>×´µ஺CN-ḄÔឋéÑ᪶ឋÑ᪶ឋ¬ê஺£09ëNH/CHCCH,CHPh\—30èÔឋÑ᪶Öᑺ>×´µ஺ìÀí▽ḄÔឋéÑ᪶ឋÑ᪶ឋ¬ê஺£CHCH337z-PrHC-VcH=C-CHO-^->Ii-Pr-^-CHCH-CHOjp2C=C´µC=O´µ¬᧕ᓄÀ!£13ஹïðᑡᑡᓄᔠᱥ:02-KH`⏨2-xJ-3,5,6-qKH`òOC1বC10

541,5-UK-9,10óô4,4-ὶ`⏨rᓝBtö⏚ᐸø¦ᱥ1ஹïðᑡᓄᔠᱥᡈᑏù᪀(:CH3cH(OH)ஹHপzC=Cx(E)-4-xJ2iT⏚HCOOHCH3cHᓰ2cHeH஺’CHOOHফ3-ûxJ`Ji⏚(3)HC=CCHCOOH3-Sᯋ⏚2CH3cHeH2cH2coOH(4)4-hiJi⏚2ஹᵨGrignardᔠᡂþ᝞ÿᑴᜓᑡ⏚(1)2,2-ᵬ⏚CH:3CH3cH2cH2-fT~C00HCH3RMgBr!82CH3CH38+8-IMgIx-5+O=C=OCH3cH2cHBrether.CH3cH2cJMgBr^CH3CH3CH3OCH3I-IIH,OICH3cH2cH2c—C-OMgBrCH3cH2cH2C—COOHCH3CH3(2)3-⏚CH=CH—CH-HCOOH22MgCO2CH2—CH—CH2cldryether»C3CH—CH2Mge15ether»ITQCH=CH-CHCOOH22

55(3)⏚(CH3cH2cH2cH2cH2coOH)MgCH3cH2cH2cH2cH2Brether*CH3cH2cH2cH2cHzMgBrCO,HQdryether*CH3cH2cH2cH2cH2COOH3ஹᑡᔜᓄᔠᱥ!"#$⏚ឋ&'()(l)RCH20H*RCOOH(2)C1CHCOOH*CHCOOH23(3)FCHoCOOH*C1CHCOOH2(4)HOCH2cH2COOH*CH3cH(OH)COOH(1)RCHOHCHjCOOH2+1Clᐹᨵᔾᵯ6Ḅ78ᦔ:(-1),;<⏚⏚ឋ=&;1CH3ᐹᨵ?ᵯ6Ḅ78ᦔ:(+1),;@⏚⏚ឋAB஺(3)FCHCOOH>CICH.COOH2+ᔾᵯ6Ḅ78ᦔ:(-1)—F>—C1(4)HOCH2cH28OHC2H50H>0>HC=CHpKa4.7415.916255ஹᑏQR⏚*CH3180HSᓄT:ḄUᳮ஺o(5H■XḄIIH+H%OHCHC—OHCHC—OH33H-+HOHoCHbC+H一CH,C—18OCHI18OCH3

566ஹ
ᡂᑡ(1)<^-CH2coOHSOC'2>(CH2coe1)Cl/\CH3cH20H/ஹ2(2)CH3COOH(CICH2COOH)-ᵪa(C1CH2co0C2H5)oবHN03»(HOOC(CH)COOH)Ba(H)2A()24ভ<>COOH(OCHOH)27ஹᵨ⊤᪵ᡠᧇᑴᜓ2-}⏚(1)_⏚.CH3cH2cH2cH2coOHCHCHCHCHCOOH322Cl“9ACHCHCH,CHCOOH39NaOHJN21OH(2)_aHCNHO2CH3cH2cH2cHO——►CH3cH2cH2cHCN—c*CH3cH2cH2fHeOOHOHOH8ஹᑡᔜ,}⏚ᑖᵨ⏚ᜐᳮ#ᑮ¡⌕mᱥ(1)2-\⏚eH2so4CH3cH2,OCH3cH2cHec)OHOHo0CH2cH3fH2sO4CH3CH2CHCOOH—CH3cH2cHO+HCOOHOH(2)3-\⏚H+CHCHCHCOOHCHCH=CHCOOH323OH(3)4-\⏚

57HOCH2cH2cH2coOH9ஹR⏒hiᑡᓄᔠᱥjᵨlmᑮ()o⌕qᱥ?(1)H0(2)CH3NH2(3)CH3coONa(4)CH(CH)OH2323O11CHC-C1310ஹs⏚RSiᑡᓄᔠᱥjᵨlmᑮ()o⌕qᱥ?পH2O,H+(2)HO,OH(3)NH(4)1-t⏣"H+23H0,H+2CH3CH2COOH+C2H5OHHO,OH-2oCH3cH2coCT+C2H5OHIICH3cH2C—OCH2cH3-------ONH3IICH3cH2c—NH?+C2H50H0CH(CH)OHII327CH3cH2C—O(CH/CH3+CHOHH+95o11ஹᑖvᑏQcXII|„„„(1)⏚x*(2)yxḄT:qᱥ஺8CH3c——UL2H5OOCH3&—*oc2H5/CH3C-OH+C2H5180H(⏒{|)ooIIHoO,OH-IICH3C—11880c2H5---------►CHC—O'+CH18OH325(}{|)

5812ஹᵨ()~ᑺᡂᑡ?/H,Pd-BaSO\পCH3cH2cH2coe1(-9------------4►)CHCHCHCHO322/পLiAl(OBu-t)3HஹᡈὅCH3cH2cH2coe1(——QHஹO»)CH3cH2cH2CHOஹCH20HফJCH20HᔆCH20HJcH20HবCH3cH2cH2COOC2H5(ᓽ&)CH3cH2cH2cH20H(1)LiAlH,etherஹf4(4)CH3cH2cH2CONH2(------~►)CH3cH2cH2cH2NH213ஹᵨT:⊤᝞_s⏚ᵬSᑴᜓᑡᔜ⏣:(1)2-ᵬ-2-⏣<-ᵫCH3MgiᐭCH3/|>CH3CH2C—CH3OHCHCH332CH,MgI1H,0ICH3CH2COOCH3drySher»CHCHCCHCHCHCCH323323OMglOH(2)3-R-3-⏣411-ᵫCH3cHzMgBrᐭfH2cH3*/CH3cH2C—CH2cH3OHCH2CH3CH2cH3CH3cH2COOCH3CH3cH28cH2cH3H2O>I—a3CH3cH2CCH2cH3H+OMgBrOH

5914ஹᵨ᪵ḄGrignardᑺ£¤⏚¥ᔠᡂ3-⏣ᵨᑏRᔠᡂ¦§஺0H0mCH3cH2—CH-CH2cH3ᡠ"ᵨᵬ⏚SHU—OC5'ᧇ஺'ஹ¨Xઙ'ᵫ1H3cH2MgBrªᐭCH2cH3HCOOC2H3HCCHCHCH3cH2fHeH2cH323OMgBrOH15ஹ(1)ᑏR(C/bCCOOH¬(CH3)3CCNḄ®¯஺P஺(CH)CCOOH+NHߟ►(CH)CCONH——►(CH)CCN33333233AᡈὅSOC1NHPQ523(CH)CCOOH——^►(CHa^CCOCl--►(CH)CCONH——>(CH)CCN33332A33ফ᝞±²(CEbCBr£NaCN³ᵨᑮ(CHjbCCN,´▭ᑮḄ¶mᱥ(CH)CCBr+NaCN——►(CH)C=CH+HCN+NaBr3332216ஹᑏR£NaOH·H^NCOCH2cH2cH2coN¸Ḅ¡⌕mᱥ஺oo.IIIIH2NCCH2cH2cH2CNH2+Br+NaOHߟ►H2NCH2cH2cH2NH22(Hoffman)ᓝ¡¢£ᓄᔠᱥ1ஹ
ᡂᑡ¬NO2

60C(CH)33

612ஹᑡᑡᓄᔠᱥᢥ⏚ឋᜧ)᣸ᑡ:OHOH0H¼প⏚ឋB>C>A>D(2)⏚ឋD>C>A>B3ஹᑖᢣRᑡᓄᔠᱥ¶½¾¿¶ᾦÁ¾#Pᵨ1°ஹ2°ஹ3°⊤RᐸÃ1ÄஹÅஹƾuÇ஺ᾦÈÉƾ#3°¾ᾦÁÉľ#1°¾ᾦÁÉž#2°¾½✏Éľ#1°¾4ஹVWᑡᓄᔠᱥ+(1)CH(CH2)4CHN(CH3)31'ỚᓄgᵬËÌ32N,N"-e(B-ⅉ)ÎÏe¾CH3cHOCH£HN(CH3)2(4)-2-(eᵬÐ)ÑCH3(5)H3c3NHÒÓCH34,4ஹeᵬeϾ

62CH3cH2cH2cHeL(6)+IÔÕᓄgᵬ1-ᵬÖÌN(CH)OH-335ஹᡂᑡ:(1)NH,AX3ফNaOBr)(3)CH=CH-CH=CH2——►H2N(CH)NH2262Cl(lmol)2NaCN9CH=CH-CH=CH—C1CH2cH=CHCH2cl---------►22NCCHCH=CHCHCN*/N»HN(CH)NH222262CHCH33H--------CONH(..N'n°B'A)H--------NH(4)226ஹᑡপᖪ´µ¶'ᢙὁᑺ3C.H¹Lপឋº»'¼½Ḅ¾¿ᢙὁᓄᑺ஺~ᵫÀ:ḄÁ*aᡈÂÃᔠᡂÄ஺CH3NHCH(CH)NHCHCH2cH(CH3%32(I)(II)C3HNH^^-NH2+(CH)C=O32

635NHCH(CH)23(I)NiNH2+CH3CCH2cH@3)2—►CH3QNH<~y-NHCHCH2CH(CH3)2(II)7ஹÅᑡÆᓄᔠᱥḄyឋᵫᜧÈ.᣸ᑡᡂÊপ(A)C^N-H(B)NH(C)B>C>DNHNH2pX9Ap(2)(A)[Ij(B)Ë)OCHD3NO2CH.Q—ᨵ+1NO2ᨵ-INC>2—ᨵ-1ஹ-CyឋA>B>C>D8ஹCHO^2XNH-CCHͶÎÏÐÑ(phenacetin),¹Ò╋ÔÕᱥ253OH(□APC!Ḅ1Ìo⌕ᡂᑖ/=kͶ°salmid/¹1Ìᑭ×k/>—I?0ÕᱥrnͶØÙ"¹1Ì◀₝ᑺ஺~há'ᧇᔠᡂÜᓄᔠᱥ(ᐸÞ~ᑺß⌱)஺(P500)জphenacetinḄᔠᡂC1G-H^OTC1HCXN02c2H50HAC2H50

64C,HO-==yNH2CHâ஺
2஺_/=\6cH5JvvL2Ho5U-\\°-NNHH-CCri3ঞØÙḄᔠᡂ:CH3cH2co%O---------NH2ফ.஺HOOCHBrBr

65NO210ஹᑏRᑡÜÌÝÞßᑖ¼à#ᡂḄ¡⌕cáḄY᪀CH3(1)[(CH)CHNCHCH]+OH-——►(CH=CH+(CH)CHN(CH)3223223232CH3N(CH)33(3)[CH3cH2cHeH(CH3)2âOH'——►(CHCH=CHCH(CH)+N(CH)3323311ஹ
ᡂᑡ¬►IHC3+H2OHC2äCH=CH—CH=CHCH23/1\(1)æçCH3I//~~\+\ফ(_^NHফéAg?஺a(V^N(CH3)3°HJ2

6612ஹᵨgᵬ¾£ᔠ〉Ḅᧇᑴᜓᑡᓄᔠᱥ(P510)(1)[(CH3)3NCH2cH20H]+OH-(×y)...\----7HiO+(CH)N+í/—[(CH3)3NCH2cH20H]OH33ফ[(CH3)3NCH2cH2cl]+cr(îïð)M1lmol-(CH3)3N+C1CH2cH2cl---------►[r(CH)NCH2CHC1]+Cä332Oব[(CH)NCHCHOCCH]+OH-(R⏒×y)33223•----7H)O+(CH3cC)஺r(CH)N+\/—[(CH3)NCHCHOHJOH----------------►o330322+II[(CH3)3NCH2cH2OCCH3]OH(4)hᓄ×y[(CH3)3%H2cH20H-cr1(CH)N+C1CH2cH20Hߟä[(CH3)NCH2CHOH]Cä3332ᡈὅ[(CH)NCHCHOH]OH--------►[(CH)NCHCHOH]er3322332213ஹᵫᢣäᧇᔠᡂᑡᓄᔠᱥo(1)ᵫs⏚ஹRÁ*ò{R}ᔠᡂó⊈õZߟN-cCHCHoBr஺HN2\7AIO/ߟ\\/+H2NCHCHNH--------2---3---►HNNH222OA,-2HO\/2CHᡝCHCOOHḄ-ABrCH2cH2coOH,஺஺R4BrCH,CH,COClOH-He二HNCBrCH2cH2coe1+HN/NH(2)ᵫ1,3-ᔠᡂøù-66஺

67Cl2NaCN2CH=CH-CH=CH\C1CHCH=CHCHC1---------->NCCHCH=CHCHCN222222(imol)(A)H,H2NCH2cH2cH2cH2cH2cH2NH2X(B)HoOH2HOOCCH2cH=CHCH2coOH—>►HOOCCH2cH2cH2cH2coOHHN1(C)û+©ᧅ/@2/NH™…I14ஹᑏRᑡ½¾åæᓄmᱥḄ᪀⌼NaNO,HC12(D4-ᵬáÁ1—or-AUL3C5NaNO,HC1//=\+TTT2H3c

68(2)ᵫᵬ⏚ᔠᡂ2,4,6-ᵬ⏚(2)ᵫᵬᔠᡂ
ᵬ(4)ᵫᔠᡂ3,5-

6916ஹᡂ!ᑡ#$:

7017ஹ
ᡂᑡᔜ(E)18ஹᵫÏஹⅉᧇᔠᡂᑡêᧇP522

71NO2NH2H,Ni2NO2NH2NH2N=NNH2ফNH2NHCOCH3NHO:g3Fe+HCl.(CH3CO)2OorH,NiM------------->HSO22419ஹᡂ!ᑡᔜ9:;HSO^^-24CHCH2CH2CH3+2H2O^JHCHCH2CH2CH3পCNCOOH<ឋᩩ?@AᱥCDEᓄ!ফ(1)KOH,CHOH,A25CH(CH)CN+2HOA(CH(CH)COOH)3292329ফH+