化学考研微群：http:/q.weibo.com/652021 合成题合成题合成题合成题(I) 1、由甲苯、丙二酸二乙酯及必要试剂合成： OH3CCH2CH3解：CH3CH3CH2Cl+ CH2O + HClZnCl2( I )(1) H2O/H+(2) , -CO2CH2(COOEt)2NaOC2H5-CH(COOEt)2Na+( I )H3CCH2CH(COOEt)2(1) NaOC2H5(2) C2H5BrH3CCH2C(COOEt)2CH2CH3H3CCH2CHCOOHCH2CH3SOCl2H3CCH2CHCH2CH3COClAlCl3CH3 OCH2CH3(TM)2、由 C3或 C3以下有机物合成：OCOOHO解： CH3CCH3O NaOH , 减压蒸馏2(CH3)2C=CHCCH3O(II)CH2(COOEt)2 (2) ( II )(1) NaOEt (CH3)2CCH2CCH3OCH(COOEt)2(1) H2O/H+(2) , -CO2(CH3)2CCH2CCH3OCH2COOHHCNOOCN - H2OCC CH3O HOOCHOCNCH3HOO化学考研微群：http:/q.weibo.com/652021 H2O/H+ OOCOOH4、由乙炔、C2或 C2以下有机物合成：OH (叶醇，一种香料) 解： CH3CH2CCMgBrO干醚H2OH+CH3CH2CCCH2CH2OHH2lindlarC=CHHCH2CH2OHCH3CH2CHCHCHCNaCHCCH2CH3Na液NH3C2H5BrC2H5MgBr(TM)5、由Br为有机原料合成：COOCH3解：BrNaCNCNH2OH+COOH COClCHOSOCl2H2/Pd-BaSO4BrCOOH COOHBrCOOCH3Br CH3OH/H+KMnO4NaOH/醇Br2/PCOOCH3ZnBrZn干醚CHO干醚H2OH+COOCH3OH- H2OCOOCH3(TM)6、由O合成CH3OH解：OCH3OHCH3CH3MgI干醚H2OH+H2SO4化学考研微群：http:/q.weibo.com/652021 (1) B2H6(2) H2O2 , OH-CH3H OHH(TM) 7、由丙二酸二乙酯合成COO- N+H3解：Br2BrCH(COOEt)2CH2(COOEt)2 NHOOKOH NKOOBrCH(COOEt)2 NCH(COOEt)2OO(1) C2H5ONa(2) (CH3)2CHCH2ClNC(COOEt)2OOCH2CH(CH3)2(1) H2O/H+(2) , -CO2(CH3)2CHCH2CHCOOHNH2NH3COO-+即：8、由苯合成IClClCl解：NO2NH2NHCOCH3HNO3H2SO4(CH3CO)2OFe + HCl NHCOCH3NH2NHCOCH3NH2ClClFe + HClCl2NaNO2+过量HCl0-5 C。NHCOCH3NO2HNO3 H2SO4NHCOCH3ClClClNH2ClClClNHCOCH3N2 Cl-ClCl +N2 Cl-ClClCl+CuClH2O/OH-NaNO2+过量HCl0-5 C。化学考研微群：http:/q.weibo.com/652021 IClClClKI(TM) 9、由邻苯二甲酸酐、丙二酸二乙酯合成：NC-OHHO解：Br2BrCH(COOEt)2CH2(COOEt)2 OOONKOONCH(COOEt)2OOBrCH(COOEt)2(2) KOH(1) NH3 , (1) NaOC2H5(2) Br(CH2)4BrNC(COOEt)2OOCH2(CH2)3Br(1) 5%NaOH(2) H+(3) , -CO2H2NCHCOOHCH2BrCH2(CH2)2NaOHNCOOHH(TM)分子内SN210、由 C4或 C4以下有机物合成： CH2OHHOHOCH2OH解：OOO+OHHOO2 C2H5OHCOOEtCOOEtCH3CO3HNa + C2H5OHH2OH+COOEtCOOEt O COOEtCOOEtHOHOCH2OHCH2OHHOHO化学考研微群：http:/q.weibo.com/652021 11、由苯甲醛、C3或 C3以下有机物合成：CH2CHCH3NH2解：CHOCH=CCOOHCH3+ (CH3CH2CO)2OC2H5COOKH2/NiNH3 , NaOBr/OH-CH2CHCOOHCH3CH2CHCONH2CH3CH2CHNH2CH3(TM) 12、由苯、C3或 C3以下有机物合成：COOHCH3CH2CH2I解：CH2CH2CH3+ CH3CH2CClO AlCl3Zn-Hg/HClCH2CH2CH3NH2(1) 混酸(2) Fe+HCl(CH3CO)2OCH2CH2CH3NHCOCH3HNO3H2SO4CH2CH2CH3NHCOCH3NO2NaNO2+过量HCl0-5 C。CuCNH2OH+ or OH-CH2CH2CH3NH2NO2CH2CH2CH3N2+ Cl-NO2CH2CH2CH3NO2CNNaNO2+过量HCl0-5 C。CH2CH2CH3NO2COOHH2O/H+ CH2CH2CH3NH2COOHFe + HCl化学考研微群：http:/q.weibo.com/652021 KICH2CH2CH3N2+ Cl-COOHCH2CH2CH3ICOOH13、由 C4或 C4以下有机物合成：OOCHCH2COOCH3CH3解：2 CH3COOC2H5(1) NaOC2H5(2) CH3COOHCH3CCH2COOC2H5O(1) NaOC2H5(2) ClCH2COOEtCH3CCHCOOC2H5OCH2COOEt(1) 5%NaOH(2) H+(3) , -CO2CH3CCH2CH2COOHO(1) SOCl2(2) C2H5OHCH3CCH2CH2COOC2H5ONaOC2H5OO(1) NaOCH3(2) CH3CH=CHCOOCH3(3) CH3COOHOOCHCH2COOCH3CH3(TM) 14、由苯、C4或 C4以下有机物合成：C-CH2CH3CH3OH解：BrMgBrBr2FeMg干醚H2OH+CCH2CH3CH3OHCCH2CH3CH3OMgBr CH3COC2H5干醚化学考研微群：http:/q.weibo.com/652021 15、由苯、C4或 C4以下有机物合成：Ph-CH2CHCOOH CH3解：CH2Cl+ CH2O + HClZnCl2CH3COOHCH2COOHCN CH2(COOEt)2Cl2PNaCNC2H5OH , H2SO4NaOEtPhCH2ClCH3INaOEtPhCH2CH(COOEt)2PhCH2C(COOEt)2CH3(1) H2O/H+(2) , -CO2PhCH2CHCOOHCH3(TM) 或者： CHO+ CO + HClAlCl3-CuCl(CH3CH2CO)2OC2H5COOK , H+CH=CCOOHCH3CH2CHCOOHCH3H2 (1mol)Ni16、由苯或甲苯、C4或 C4以下有机物合成：H3CBrBr解：Br2-H2OCH3CH3NH2CH3NH2BrBrBr2-H2O混酸Fe+HClCH3NO2H3CN2+ HSO4-BrBrH3CBrBrNaNO2+过量H2SO40-5 C。H3PO2 + H2O17、完成转化：ClCH2CH2CHOCHCH2CH2CHOOH化学考研微群：http:/q.weibo.com/652021 解：ClCH2CH2CHOOOClCH2CH2CHHOCH2CH2OH干HClMg干醚OOClMgCH2CH2CHH2OH+PhCHOPhCHCH2CH2CHOOH(TM)干醚18、完成转化：CHOHOCH2CH3CHOO解：CHOO2 CH3OH干HClCHOOCH3OCH3C2H5MgBr干醚CHOHOCH2CH3H2OH+19、完成转化：CCHOHH3CC2H5HH5C6C=CC6H5CH3 HC2H5解：CCHOHH3CC2H5HH5C6TsClCCHOSO2C6H4CH3-pH3CC2H5HH5C6NaOH 醇 , C=CC2H5HCH3C6H5(注：TsCl = 对甲苯磺酰氯) 20、由甲苯合成：H3CCNBr解：CH3CH3NO2CH3NO2BrCH3NH2BrHNO3H2SO4Br2FeFe + HCl化学考研微群：http:/q.weibo.com/652021 CH3N2+ Cl-BrCH3CNBrNaNO2+过量HCl0-5 C。CuCN21、由PhCH=CHCHO PhCH2ClCH2OHCH2OHPhPhO O、解： PhCH2ClMg干醚PhCH2MgClPhCH=CHCHCH2PhOH PhCH=CHCHOH2OH+PhPh- H2OC=CHCOOEtHEtOOCPhPhCOOEtCOOEtKMnO4稀、冷 ，OH-PhPhCOOEtCOOEtHO HOCH3COCH3干 HClPhPhCOOEtCOOEtOO(1) LiAlH4(2) H2OPhPhCH2OHCH2OHOO22、由CH3OCH3OO解：OCH3OCH3CCH2CH2COOHOOCH3CH2CH2CH2COOHZn-Hg/HClOOOAlCl3OCH3CH2CH2CH2COClCH3OO SOCl2AlCl3化学考研微群：http:/q.weibo.com/652021 23、完成转化：CH3CH2CCH2BrOOCH2CH3O解：CH 3CH2CCH2BrO HOCH2CH2OH干HClOOCH3CH2CCH2BrCH2(COOEt)2NaOC2H5OOCH3CH2CCH2BrOOCH3CH2CCH2CH(COOEt)2(1) H2O/H+(2) , -CO2CH3CH2CCH2CH2COOHO NaBH4CH3CH2CHCH2CH2COOHOH- H2OO CH2CH3O 24、由丙二酸二乙酯合成CH2=CH-CH2-CH-C-OC2H5OCH3解：CH2(COOEt)2CH2=CHCH2CH(COOEt)2NaOC2H5CH2=CHCH2ClCH2=CHCH2C(COOEt)2CH3CH2=CHCH2CHCOOHCH3NaOCH3CH3I(1) H2O/H+(2) , -CO2CH2=CHCH2CHCOOC2H5CH3C2H5OHH+25、由环己醇合成O CH3解：OHHOOC(CH2)4COOHH5C2OOC(CH2)4COOC2H5浓HNO3C2H5OHH+OCOOC2H5C2H5ONaNaOCH3CH3IOCOOC2H5 CH3化学考研微群：http:/q.weibo.com/652021 (1) H2O/H+(2) , -CO2OCH3 26、由苯酚、O 合成CH3OO解： CH3OOSOCl2AlCl3OCH3OCH3CH2CH2CH2COOHZn-Hg/HClOOOAlCl3浓H2SO4 , H2O(1) HCCNa(2) H2/lindlarCH3OHOCH=CH2 CH3OCH=CH2OOCH3O27、由甲苯合成：CH3 BrBrCH2CH3解：CH3CH3COCH3CH3COCH3BrBrCH3CH2CH3BrBrCH3COClAlCl3Br2FeZn-HgHCl29、由 C3或 C3以下有机物为原料合成： HO-C-CH2CH2CH2-C-OHOO解：CH2(COOEt)2NaOEtCH2=CHCNCH2CH2CNCH(COOEt)2(1) H2O/H+(2) , -CO2HOOCCH2CH2CH2COOH 化学考研微群：http:/q.weibo.com/652021 31、由 C4或 C4以下有机物为原料合成：O解：CH3CC