COOHCHO5.CH2OHOH稀HCl稀NaOHCHOCH2OHONa稀HClCOONaCHO稀HClCOOHCHSO3NaOHCH2OHOH饱和NaHCO3CH2OH饱和NaHSO3OHOH
NH26.NHCH3N(CH3)2(1)(2)NaOHSO2Cl蒸馏N(CH3)2SO2NNa+SO2NCH3过滤SO2NNaSO2NCH3稀HCl稀HCl稀NaOH稀NaOHNH2NHCH37.加冷浓H2SO4，苯甲醚溶解，分层，酸层加热即复得苯甲醚。 8．用浓H2SO4可除去噻吩。 9．用Na可除去1-己醇。
10．先用饱和NaCO3除去苯甲酸，然后用饱和NaHSO3溶液除去苯甲醛。
六、以给定的有机物为原料，无机试剂任选，完成下列转化
KOH-C2H5OHHBrCH3CHCH31.CH3CH2ClCH3CH=CH22.CH3CH=CH2Cl2。500C
BrCH2CH=CH2ClCl2CH2CHCH2ClClCl3.CH3CH=CH2HBrCH3CHCH3BrKCNCH3CHCH3CNH3O+CH3CHCOOHCH3 30
4.CH2=CH2-稀OH浓H2SO4CH3CH2OSO3HH2OCH3CH2OHCuCH3CHO5.CHCHMgH2-NiCH3CH=CHCHOH2OCH3CHOHgSO4-H2SO4CH3CH2MgBrCuCH3CHOCH3CH2CH2CH2OHH2-NiPBr3CH3CH2OHCH3CH2CHCH3OMgBrCH3CHCH2CHOOHH2-NiCH3CH2BrCH3CHO稀OH-H2O无水乙醚6.CH3CH2OHCH3CHOHCl(干)CH3CHCH2CH3OHCH3CHCH2CH2OHOHCH3CH7.CH3ClAlCl3H3O+OCH2CH2OCHCH3Cl2CH3CH2ClKCNCH2CNCH2COOHO8.CH3[O]COOHSO2ClCClNH3OCNH2
Br2-NaOHNH2
9.CH2=CH2Cl2CH2CH2ClClKCNCH2CH2CNCN-稀OHCOOHH2-NiorLiAlH4CH2CH2CH2CH2NH2NH2
10.CH311.(1)O3(2)Zn/H2O浓HNO3浓H2SO4CHOCHOCH3[O]NO2CHO
H2-NiCOOHNO2NH2
31
12.CH3CHO[O]CH3COOHOPCl3OCH3CClAlCl3H2-NiOCCH3浓HNO3浓H2SO4CCH3NO2浓H2SO4I2-NaOHNO2COOHCOOHNH213.CH2=CH2CH2=CH2H2O
CH3CH2OHKCNCH2CH2CNCNH3O+CH2 CH2COOHCOOHCl2CH2CH2ClCl14.C2H5OHCH2COOC2H5+H/CH2COOC2H5NH2NaNO2C2H5OHN2ClHClorH3PO2CH3CH3HNO3?¨H2SO4?¨NO2CH3NaNO2HClH3PO2BrBrN2ClBrBrFe-HClNH2CH3CH3NO2浓HNO3浓H2SO4CH3Br2/H2OBr Br2FeNO2Br
15.BrNH216.OCNH2浓HNO3浓H2SO4NO2N2ClH3O+OCNH2
Br2-NaOHNO2NH2NaNO2HClNO2OHNO2
32
CH317.浓HNO3浓H2SO4CH3KCNCuCNCN18.CH3CH2COOHBr2-NaOHPCl3CH3Fe-HClNO2H3O+COOHOCH3CH2CClCH3NaNO2HClNH2CH3CH3N2ClNH3OOCH3CH2CNH2O
CH3CH2NH2CH3CH2CCl19.CH3CHOHCNCH3CHCNOHPCl3CH3CH2CNHC2H5 H3O+CH3CHCNCl20.CH3CHCOOHNH3CH3CHCOOHNH2Cl
CH=CHCH3(1)O3CHO稀OH-+CH3CHO(2)Zn/H2OCH=CHCHO
21.CH3CH=CH2(1)浓H2SO4(2)H2OCH3CHCH3OHPBr3MgCH3CHCH3无水乙醚BrH2OCH3CHCH3MgBrMgBrCH3CHCH3OH浓H2SO4[O]CH3CCH3OCH3CHCH3CH3CH3CCHCH3CH3OH
22.HNO2CH3CH3C=CCH3CH3NO2NH2Fe-HClBrBrBrBr2/H2OBrBrNH2Br浓HNO3浓H2SO4H3PO2
33
CH3CH3浓HNO3浓H2SO4CH3Fe-HClBr2/H2OCH3Br23.BrNO2CH3CH3H3PO2[O]BrBrBrBrNH2NH2COOHNaNO2HClBrBrN2Cl
CHOCHO+HCHOOCH3OCH324.CH=CH2(1)O3(2)Zn/H2OHCHOH2-NiCH3OHCH(干)HCl25.CH2=CHCH=CH2H2-NiCl2CH2CH=CHCH2ClClKCN
CH2CH=CHCH2CNCNCH2CH24CH2NH2NH2
七、从指定的有机物出发，合成下列化合物（其它无机、有机试剂任选）。
1.CH2=CH2HBrCH3CH2BrHBrMg无水乙醚CH3CH2MgBrCH2CH2O
H2OCH3CH2CH2CH2OHH3O+CH3CH2CH2CH2BrKCNCH3CH2CH2CH2CN2.CH3CH2OHCu[O]CH3CH2CH2CH2COOHCH3CHOCH3MgBrCH3MgBrH2OH2O
CH3CHCH3OHCH3CH3CCH3OCH3CCH3OHCH2OH HCHO浓OH-(HOCH2)4C3.CH3CH2OHCuCH3CHO3CH2O稀OH-HOH2CCCHOCH2OH
34