第一部分：烯烃1.2hv2.23.Br4.25.26.Cl -H O7.IClH IClH 8.9.CH 3CHCH CH 23D 2Pt10.11.412.(1)OsO 4吡啶(2)NaHSO 3(1)(2)13.CF 3CO 3H H 3O +(1)(2)14.CF 3CO 3H H 3O +(1)(2)15.F 3CH 2SO 4浓H 2O16.17.HBr ROOR18.(1)(2)19.B 2H 6H 2O 2/OH(1)(2)20.O 3Zn/H 2O21.KMnO 4+22.CF CO H23.CF CO H24.CF CO H第二部分：炔烃和二烯烃1.NaNH 3(l)2.H 2Lindlar3.H OHgSO 4/H 2SO 44.(1) B 2H 6(2) H 2O 2/OH5.HCN6.(1) B 2H 6(2) CH 3COOH -7.3OH 3C 2H 5ONa8.9.Br10.11.12.H Lindlar KMnO13.H 214.Br 315.Br 216.2Cu Cl / NH Cl17.2NH 3(l)2518.19.2低温 20.2高温Br Cl21.22.CNCN+23.COOCH 3+H 3COOC24.+25.+OO26.(1)O 32+Cl 227.第三部分：脂环烃NBS1.2.2Ni3.HBr4.(1)(2)H 2SO 4浓H 2O5.CH 2 / Ni806.第四部分：芳香烃1.NBS hv2.4H +3.BrCOOH4.+Cl35.+3(CH 3)3CCl1006.3O7.HSO HNO 3H SO NO 28.(浓)165H SO9.(浓) 2310.3 2311.3+3(CH 3)3CCl12.O13.O O14.NO 2KMnO / H +15.NH 2KMnO / H +60H SO16.(浓)17.BrHNO 318.BrOH19.NO 2COOH20.22AlCl 3第五部分：卤代烃1.BrKOH / 醇2.(CH 3)3CClNaCN / 醇BrClNaOCH / 醇3.4.ClBrBr 5.KOH / 水6.BrClBr Br7.C H ONa / 醇8.(CH 3)3CCH 2I3醇Br Cl9.NaI CH 3COCH 3醇10.BrCOOCH 3CH 3H11.C 2H 5CIH 212.Cl OH Ca(OH)ClOHCa(OH)13.14.C 2H 5C Cl2215.C 2H 5CBr22CH 3Cl H2H 5H SCH 3216.17.CH 2Br CH 2Br318.BrCl NO 2219.OCH 3Cl220.CH 3ClNaOH / H 2O21.H 2H 522.BrNaOC H / 醇23.BrFCl24.Br25.ClCH 2ClO(2) H 3O +第六部分：醇、酚、醚1.OC(CH 3)3HI(过量)CH 3OC(CH 3)32.CH 3OC(CH 3)33.4.OHH +5.CH 3H Ph Br HNaOC H6.CH 2OHOH(CH 3)2SO 47.CH 2OH OH3H 2SO 48.H +9.OHHOHCH 32H 52乙醚10.HOHCH 32H 52吡啶11. 12.CH 2OH PCC13.OH OHHIO 4+OH14.15.H +OH OH16.33(2)CH 3OH, HO17.Ph3-325+18.O19.OHH20.异丙醇铝33OH第七部分：醛酮醌1.ClOO 322.O2乙醚NH 4Cl 2 H 2O / H +3.OHCN2+4.HCHO+CH 3C CNaO 5.NH 2OHOHSCH CH SHH +6.+7.O+NH8.O H ++OH OHOH22+CHO 6H 5H 3C H9.10.C CH 3N OHH SO(CH )CuLi2+11.OPhLi2+12.O13.2乙醚2+14.PhO25乙醚2+15.PhO16.O(Ph)P +CHCH -+17.C 6H 5COCH 3HCHO +(CH 3)2NH++18.OC 2H 5OOC2H 5吡啶19.O吡啶CH (COOH)O20.O+-O+-21.CHO22.O23 23.OOH+24.CHOOH (CH 3CO)2O+CHOHCHO25.26.OCHO27.OCF 3CO 3H28.OOOOO H 3COOOH 3COO29.30.OMg, 苯3+H 3O +31.O LiAlH(s -BuO)32.NaBH O3+O33.LiAlH 4第八部分：羧酸CH 2CH 2COONa3H OH 1.++2.CH 2Cl CH 3COONa33.COOHCH 2COOH4.COOHCOOHH 3O +COOHCH=CH 25.46.COOHNa, NH (l)3+7.(CH 3)3CCOOHLi CH 3NH 2 8.COOH B H29.COOH 2 10.OH COOH11.COOH2 12.COOH NO 2第九部分：羧酸衍生物1.NHCCH 2CH 2COOCH 3OOH -2.C 2H 5OCCH 2CH 2CClO O243.18OC(CH 3)3OH 3O +OH -4.18OC 2H5OCOC 2H 5O COOC(CH 3)3CH 3OH -H 2O 6.COC 2H 5O COOC(CH 3)3CH 327.+ (CH 3CO)2O 8.+HOCH 2CH 2NH 223 (CH 3CO)2O 9.+HOCH 2CH 2NH 210.CONH 2ClP 2O 511.CONH 2ClBr OH12.O+BrCH 2COOC 2H 5Zn C 6H 62 O +H 2O13.COOC 2H 52514.C 2H 5OOC 2H 515.CH 3CH 2COOC 2H 5H 2O乙醚16.COOC 2H 5NaC 2H 5OH2OO 17.2N(CH 3)2O18.42CH 3COCl19.PhMgBr低温20.H 3CCOOCOOCH 33CH 3ONa(少量)(CH 3)3CCOOH5.C 6H 5OH 吡啶2+21.OBrCH 2COOC 2H 525第十部分：含氮、含硫化合物1.CH 3NO 2HCHO(过量)OH -+CN CH 3CH 2NO 2OH -2.O 2NNO 23.4O 2N4.Zn H +OCH 35.3)2H 3CO6.N 2+Cl -OH3+HOOC N 2+Cl -+7.N(CH 3)2+NH8.O9.NH 2POCl 310.NH 23(2) Ag 2O,H 2O 32211.O NH 2+12.O CH 3CH 2NH 2H 2(2)13.OC 6H 5CH 2Cl3+NH 214.H 3C 2CNH 3CNH 2HOOC2IH 3C15.NH 2HOOC 216.HBrNH 2HOOC217.322H 2O18.CH 3CH 2COCl2219.CH 2NH 2OH20.OClNaOC 2H 52520.H 3CCOO 316521.OCH 2CH=CHPh22.NC223.24.SO 2ClCOClH O第十一部分：杂环化合物、碳水化合物和氨基酸1.NH 2+CH 2OH CHOH 2OHPhNO , H SO (浓)O2.CH 3HClSCH 33.O 2NCH OO4.+COOCH 33NHO 2N5.Br OO6.N CH 37.N HC H MgBr328.N2N29.PhN10.11.N4+12.NCH 3C H CHO 2N13.CH 3252NaOC2H 5N14.Cl15.CHO2OH C H NHNH (过量)16.CHO2OH 2217.CHO2OH 3OOHOHOHCH 2OH18.CH CH OH 干HCl19.CH 3CHCOOHNH 2CH 3CHCOOH220.O 2NNO 2F+。