有机合成经典习题及答案

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1、化学考研微群：http://q.weibo.com/652021合成题(I)1、由甲苯、丙二酸二乙酯及必要试剂合成：H3CCH2CH3OCH3CH3ZnCl2+CH2O+HCl解：CH2Cl(I)NaOC2H5-+(I)CH2(COOEt)2CH(COOEt)2NaH3CCH2CH(COOEt)2CH2CH3(1)NaOC2H5(1)H2O/H+H3CCH2C(COOEt)2H3CCH2CHCOOH(2)C2H5Br(2)D,-CO2CH2CH3SOCl2AlCl3H3CCH2CHCH2CH3CH2CH3CH3COClO(TM)OOCO

2、OH2、由C3或C3以下有机物合成：OONaOH,D解：2CH3CCH3(CH3)2C=CHCCH3减压蒸馏(II)OO(1)NaOEt(1)H2O/H+CH2(COOEt)2(CH3)2CCH2CCH3(CH3)2CCH2CCH3(2)(II)(2)D,-CO2CH(COOEt)2CH2COOHOHOCNOOCNHOOCCCH3HCNHOOC-H2OCH3D化学考研微群：http://q.weibo.com/652021OOCOOHHO/H+2D4、由乙炔、C2或C2以下有机物合成：OH(叶醇，一种香料)解：NaC2H5BrC2H5M

3、gBrCHCHCHCNaCHCCH2CH3液NH3CHCHCCMgBrOH2O32CH3CH2CCCH2CH2OHH+干醚H2CH3CH2CH2CH2OHlindlarC=C(TM)HH5、由Br为有机原料合成：COOCH3NaCNH2O解：BrCNCOOHH+SOCl2H2/Pd-BaSO4COClCHONaOH/醇KMnOBrBr4Br2/PCOOHCOOHBrZnBrCH3OH/H+ZnCHOH2OCOOCH3干醚H+COOCH3干醚-H2OCOOCH3DCOOCH3(TM)OHCH36、由O合成OHCH3MgIH2OCH3H2S

4、O4解：O+CH3干醚HOHD化学考研微群：http://q.weibo.com/652021CH3(1)B2H6H(2)H2O2,OH-(TM)HOH-COO7、由丙二酸二乙酯合成+NH3Br2解：CH2(COOEt)2BrCH(COOEt)2DOOOKOHBrCH(COOEt)2NHNKNCH(COOEt)2OOOO(1)C2H5ONa(1)H2O/H+NC(COOEt)2(CH3)2CHCH2CHCOOH(2)(CH3)2CHCH2Cl(2)D,-CO2OCH2CH(CH3)2NH2COO-即：+NH3Cl8、由苯合成IClClN

5、O2NH2NHCOCH3解：HNO3Fe+HCl(CH3CO)2OH2SO4NHCOCH3NHCOCH3NHCOCH3HNO3Fe+HClCl2NaNO2+过量HClH2SO4。ClCl0-5CNO2NH2NH2NHCOCHNHCOCHN+Cl-33NH22CuClH2O/OH-NaNO+过量HCl2。ClClClClClCl0-5CClClN+Cl-Cl2ClCl化学考研微群：http://q.weibo.com/652021IKI(TM)ClClClO9、由邻苯二甲酸酐、丙二酸二乙酯合成：C-OHNHBr2解：CH2(COOEt)2

6、BrCH(COOEt)2DOOO(1)NH3,DBrCH(COOEt)2ONKNCH(COOEt)2(2)KOHOOOO(1)5%NaOH(1)NaOC2H5(2)H+BrCH2(CH2)2CHNC(COOEt)22(2)Br(CH2)4Br(3)D,-CO2HNCHCOOHCH2(CH2)3Br2ONaOHCOOH(TM)分子内SN2NHHOCH2OH10、由C4或C4以下有机物合成：HOCH2OHOOHCOOEt2C2H5OHCH3CO3H解：+OODDCOOEtOHOCOOEtHOCOOEtHOCHOHOH2ONa+C2H5OH2

7、COOEtH+HOCOOEtHOCH2OH化学考研微群：http://q.weibo.com/652021NH211、由苯甲醛、C3或C3以下有机物合成：CH2CHCH3CHO解：C2H5COOKCH=CCOOHH/Ni+(CH3CH2CO)2O2DCH3CH2CHCOOHNH3,DCH2CHCONH2NaOBr/OH-CH3CH3CH2CHNH2(TM)CH3I12、由苯、C3或C3以下有机物合成：CHCHCHCOOH322OCH2CH2CH3AlCl3Zn-Hg/HCl解：+CH3CH2CClCH2CH2CH3CH2CH2CH3CH

8、CHCH223(1)混酸(CH3CO)2OHNO3(2)Fe+HClH2SO4NO2NH2NHCOCH3NHCOCH3CH2CH2CH3CH2CH2CH3CH2CH2CH3H2ONaNO2+过量HClCuC