有机化学试题库五——合成题及解答

1试题库五——合成题及解答1．由苯或甲苯及其它无机试剂制备：2．3．4．5．6．CH3CH2CH2OH→CH3C≡CH7．CH3CH2CH2OH→CH3CH2CH2OCH(CH3)28．CH3CH2CH2CH2OH→CH3CH2CH(OH)CH39．10．CH2=CH2→HOCH2CH2OCH2CH2OCH2CH2OH11．CH3CH2CH=CH2→CH3CH2CH2CH2OH12．CH3CH2OH→CH3CH(OH)COOH13．14．15．HC≡CH→CH3CH2CH2CH2OH16．NO2COOHNO2CH3COOHClClBrClClBrCOOHBrCH3NO2BrBrNO2a.b.c.d.e.f.g.OHOOHOHSO3HCOClCOOHOCH3CH2CCH3OHCH3COOHNO2BrCH3COOHCMe3COOHNO2217．18．19．20．CH3CH=CHCH3→21．CH3CH2CH2OH→CH3CH2CH2CH2OH22．写出由相应的羰基化合物及格氏试剂合成2-丁醇的两条路线。23．由苯合成2-苯基乙醇。24．由甲苯合成2-苯基乙醇。25．26．27．28．29.30．31．32．33．(CH3)2C=CH2→(CH3)3CCOOH34．CH3CH-CHCHOOHOHBrCH2(CH2)2CH2COOHOOOCO2CH3OCH2COCH3CH3COOHCOCH3CH3COOC2H5HOOCCH-CHCOOEtCH3CH3OCOOHOHCH3CH2CH2BrCH3CH2CH2COOH(CH3)2CHOH(CH3)2CCOOHOHCH3CH3OOOOOOBrCOOHCH2CHCH2CH3OHCH2CH2CH2OHCH2CHCH3OH335．HC≡CH→CH3COOC2H536．37．CH3CH2COOH→CH3CH2CH2CH2COOH38．CH3COOH→CH2(COOC2H5)239．40．41．42．43．44．45．46．47．48．49．50．OOCO2CH3OHCOOHOOCCH3NH2NH2NH2NO2CH3CH2OHCH3CHCH2CH3NH2NH2NHCOCH3NO2NNCH3OHNNCH3NH2NH2NO2NH2NH2NO2NH2NH2NO2OHNO2BrBrBr451．52．53．54．55．由CH2(COOC2H5)2合成56．由CH3COCH2COOC2H5合成57．58．59．60．61．用丙二酸二乙酯合成1,3-环戊二甲酸。62．用丙二酸二乙酯合成1,1-环戊二甲酸。63．用乙酰乙酸乙酯合成CH3COCH2CH2CH2COOH。64．65．66．用乙酰乙酸乙酯合成67．用乙酰乙酸乙酯合成68．用丙二酸二乙酯合成1，4环已二甲酸。BrCH3BrCH3NO2NO2ClBrCHCOOHCH2CH=CH2H3CCH3CH2CH2CH2CH-CH3COOHCOOHCH3COOHCH3(CH2)3OHCH3(CH2)3SO2(CH2)3CH3CH3SO2NHH3CCH3CH3CH2BrCH3CH3BrCH3COCH2BrCH3COCH2CH2CH2OHOOBrBrBr569．70．由丙二酸二乙酯合成庚二酸71．由乙酰乙酸乙酯合成2,4－戊二酮72.73.由乙酰乙酸乙酯合成2,5－己二酮。74.由丙二酸二乙酯合成3-甲丁酸75.76.由丙二酸二乙酯合成环丁基甲酸。77.由乙醇合成乙酰乙酸乙酯。78.79.80.81.由乙酰乙酸乙酯合成3-乙基-2-戊酮。82.由丙二酸二乙酯合成83.84.由丙二酸合成2-苄基丁酸。85.由乙酰乙酸乙酯合成86.87.用丙二酸二乙酯合成环已基甲酸。88.用乙酰乙酸乙酯合成2-甲基-4-戊酮酸。89.CH3COCH3CH3CH-C-CH3CH3OHCH3NH2NO2CH3CH=CH2CH≡CH，CH3CH2CH2CCH2CH2CH2CH3ONH2NO2CHOOHOOCOOHCHOOBrOEtOOOHCH2CH3OHOHCHOOCHO690.91.92.93.94．95.96.97.98.99.100.101．102.103.104.CH3CH3OHNO2由CH3CH2CH2CH2BrCH3CH2CH-CHCH3CH3CH3CH3NO2由CH2CH2CH3BrCH2CH2CH2CH2Br由1-丁烯合成CH2ClCH2CH=CH2CH2CH2CH3BrCH2CH2CH3OHOBrBrNO2OHBrBrOH(CH3)3CCH2CHCH3Br(CH3)3CCHCHCH3(不多于四步)COOHNO2CH2CH3OHOCH2CH2CH2CH3OHOCH2ClCH2CH2CH2ClCH2CH2CH3OHO7105.由乙炔合成3,4-二羟基已烷。106.由环戊烷合成（其它试剂自选）107.由甲苯合成108.由苯合成109.110.以铜锂试剂合成1-苯基-2-甲基戊烷。111.以铜锂试剂合成2-甲基已烷。112.以苯为原料合成苦味酸()113.114.由正丁醇合成2-丁醇。115.由苯酚和两个碳原子及以下的有机物合成116.五个C原子以下的有机物合成117.以不多于4个C的有机物为原料合成：118.以丙烯为原料合成：119.以丙烯为唯一有机原料合成：试题库之五：合成题答案1．CH2H3CCH3BrSO3HCHCH3OHCOCH3OHNO2NO2O2NCH3OC2H5OHNO2NO2C-CH3OHCH3BrCH2-CH-CH2ClClBrCH3-C-CH2CH2CH3OHCH3a.CH3ClAlCl3KMnO4Cl2FeCl3COOHClNO2Brb.Br2FeBr3HNO3H2SO4CH3ClClc.Cl2CH3Cl2FeCl3FeCl3COOHCld.KMnO4Cl2CH3FeCl3NO2Bre.Br2FeBr3HNO3H2SO4COOHBrNO2f.CH3ClAlCl3KMnO4Br2FeBr3HNO3H2SO4CH383．CH3NO2BrBrg.Br2FeBr3HNO3H2SO4CH3H2SO4100℃180℃H2OCOOHNO2KMnO4Br2FeBr3HNO3H2SO4CH3BrAlBr3Br2.CH3COOHCMe3AlCl3(CH3)3CBrKMnO4CH3CH2CH2OHH2SO4Br2OH-HBr-HBrNaNH2170℃乙醇-6.CH3CH2CH2OHNaMe2CHBr7.COOHNO2KMnO4CH3BrAlBr3HNO3H2SO44.OHOK2CrO75.CH3CH2CH2CH2OHH2SO4H+H2O170℃8.OHOHSO3HH2SO4浓100℃9.CH2=CH2O2/Ag250℃H2OOO10.CH3CH2CH=CH2B2H6H2O2OH-CH3CH2CH2CH2OH11.CH3CH2OHAg550℃H2OHCN12.C6H6AlCl3COClCO13.OHOHSO3HH2SO4浓100℃9.OHONaBH414.H2SO4方法一：HgSO4OH-△NiH215.O方法二：Na液氨HBrMg干醚H2OH+15.930．CH3CH2CCH3OHCH3NBSMg干醚CH3COCH3H2OH+16.CH3CH=CHCH3H2OH+KMnO4OH-冷CH3CH-CHCH3OHOH20.HCHOCH3CH2CH2OHMg干醚H2OH+HBrCH3CH2CH2CH2OH21.HClZnCl2干醚MgCH3CH2CHOHCHO，CH2ClH3O+TM17.HClZnCl2干醚MgHCHO，CH2ClH3O+TMCH3CHO18.干醚MgHCHOH3O+TMCH3CH2BrAlCl319.HCHOCH3CH2CH2OHMg干醚H2OH+HBrCH3CH2CH2CH2OH21.干醚H2OH+CH3CH2CHCH3OHCH3CH2MgBr方法一：CH3CHO+22.干醚H2OH+CH3CH2CHCH3OHCH3MgBrCH3CH2CHO+方法二：22.Br2FeCl3MgTHFOCH2CH2OHH2OH+23.NBSMgTHFCH2CH2OHCH3HCHOH2OH+24.H2OOH-BrCH2(CH2)2CH2COOH△OO25.OH-稀OCO2CH3OCH2COCH3NaOEtCH3COCH2BrOCO2CH3CH2COCH3H+△26.CH3COOHEtOHNaOEtCH3COCH2COOEt27.COCH3NaOEtBrCH2CH2CH2Br-HBrNaOEt-HBrCOCH3COOEt稀OH-CH3COOC2H5NaOEtCH3COCH2COOEtNaOEtBrCHCOOEtHBrNaOEtHOOCCH-CHCOOEtCH3CH3CH3-浓OH-H+BrCH328.HCNH2OH+29.NaCNH2OH+①②Mg干醚CH2OH2OH+KMnO4Na2CrO7H2OH+HCN31.1032．36．41．42．43．44．46．48．49．50．KMnO4P2O5△方法一：方法二：Mg干醚H2OH+HBrNaCNHBrCO2H2OH+33.KMnO4CH3BrAlCl3Br2Fe34.H2SO4HgSO4KMnO4EtOHH+35.H2SO4Na2CrO7△△Ba(OH)2KMnO4H+LiAlH4HBrMg干醚环氧乙烷H2O37.EtOHH+H2OPBr3NaCNH+38.CH3COOHH+H2O39.H2SO4HNO3+HClFe40.H+HNO3(CH3CO)2O乙酸H+Na2CrO7HBrMg干醚CH3CHONH3Ni(CH3CO)2OFeBr2+HClFeHNO25℃C6H5NH2+HClH2SO4HNO3OHFe5℃HNO245.H2SO4OH-HNO3浓(CH3CO)2OHNO3H2OH+乙酸47.(CH3CO)2OHNO3乙酐H2OH+OH-或HNO3H2SO4NH4SHNaNO2H2SO4H2O0~5℃△△乙醇液HNO3H2SO4△Fe+HClBr2NaNO2H2SO40~5℃H3PO2+H2OHNO3H2SO4△Fe+HClBr2NaNO20~5℃H3PO2+H2OHCl52.H2SO4HNO3FeHClBr2H2SO4△(CH3CO)2OH3O+180℃H2ONaNO2HCl＜5℃H3PO2H2O51.FeCl3HBr5℃HNO2HNO3H2SO4△Fe+HClCuBr-Cl21154．58．59．FeCl3HBr5℃HNO2HNO3H2SO4△Fe+HClCuBr-Cl25℃HNO2(CH3CO)2OHNO3乙酸NaNO2HNO3H2SO4△Fe+HClHBF4Cu粉H2OH+53.FeCl3HBr5℃HNO2HNO3H2SO4△Fe+HClCuBr-Cl2NaOC2H5△H+/H2OTMCH2(COOC2H5)2CH3BrNaOC2H5CH2=CHCH2Br55.CH3COCH2COOEtEtONaCH3CH2CH2CH2BrEtONaCH3Br酸式分解TM56.CH3COOHNaCNEtOHP,Cl2NaOHH2SO4α-取代EtONaCH2(CH2Br)2-2NaBr-CO2△水解TM57.NaSHNaOHCH3(CH2)3IHNO3H2SO4PCl3CH3H2NBr2FeCH3CH2BrAlCl3Br2FeCH3COClAlCl3Zn/HgHCl60.或NaOH①EtONa②BrCH2CH2Br2①EtONa②CH2I22①②HCl△61.①EtONa②BrCH2CH2COOEtOH-63.△H2SO4HNO3FeHCl(CH3CO)2OBr2H3O+NaNO2HCl＜5℃H3PO2H2O64.H3O+TM①②2Br(CH2)4BrEtONaNaOH62.MgH3O+HOCH2CH2OH乙醚O65.NaOH①EtONa②CH3CH2CH2Br①EtONa②CH3ITM66.TM①②BrCH2CH2CHMe2EtONaNaOH酮式分解67.NaOH①EtONa②BrCH2CH2Br2①②HCl①EtONa②B