有机化学试题库五合成题及解答.pdf

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1、试试题题库库五五合合成成题题及及解解答答1由苯或甲苯及其它无机试剂制备：a.COOHNO2CH3COOHClClNO2COOHCH3BrBrNO2Brb.ClBrc.d.Cle.Brf.g.NO2COOHBrNO22CH3COOHCMe33COOHNO24OHO56CH3CH2CH2OH CH3CCH7CH3CH2CH2OH CH3CH2CH2OCH(CH3)28CH3CH2CH2CH2OH CH3CH2CH(OH)CH3910CH2=CH2 HOCH2CH2OCH2CH2OCH2CH2OH11CH3CH2CH=CH2 CH3CH2CH2CH2OH12CH3CH2OH CH3CH(OH)COO

2、HCOClOHOHSO3H1314COOOH15HCCH CH3CH2CH2CH2OH161718CH2CHCH3OHCH3CH3CH2CCH3OHCH2CHCH2CH3OH1920CH3CH=CHCH3CH3CH-CHCHOOHOHCH2CH2CH2OH21CH3CH2CH2OH 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。25OCO2CH3OCH2COC H3BrCH2(CH2)2CH2COOHOO2627CH3COOHCOCH32829.CH3COOC2H5HOOC CH-CHCOOE

3、 tCH3CH3COOHOCH3CH2CH2BrOHCH3CH2CH2COOH303132CH3OOO(CH3)2CHOH(CH3)2CCOOHOHCH3OOO33(CH3)2C=CH2(CH3)3CCOOHCOOH34Br35 HCCH CH3COOC2H5O36O37CH3CH2COOH CH3CH2CH2CH2COOH38CH3COOH CH2(COOC2H5)23940CO2CH3OHCOOHOOCCH3NH2NH2NH241NO242CH3CH2OHCH3CHCH2CH3NH243NH2NHCOCH3NO2N N44CH3NNOHCH345NH2NH246NO247NH2NH2NON

4、H2NH2NO2482OH49NO2BrBrBr50BrBrBr51CH3CH352BrBr53NO2NO2Cl54Br55由 CH2(COOC2H5)2合成56由 CH3COCH2COOC2H5合成CH3CH2CH2CH2CH-CH3COOH57CH3COOHH3C CHCOOHCH2CH=CH2COOH583(CH2)3OHCH3CHCH3(CH2)3SO2(CH2)3CH3H3CSO2NHCH35960CH3CH2Br61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。CH3CH3Br642

5、Br65CH3COCHCH3COCH2CH2CH2OH66 用乙酰乙酸乙酯合成67 用乙酰乙酸乙酯合成OO68用丙二酸二乙酯合成 1，4 环已二甲酸。69CH3COCH3CH3CH3CH-C-CH3CH3OH70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OCH CH75.CH3CH=CH2，CH3CH2CH2CCH2CH2CH2CH3NH2NO276.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.CHONH2NO279.80.OHO81.由乙酰乙酸乙酯合成 3-乙基-2-戊酮

6、。82.由丙二酸二乙酯合成83.CHOOCOOHOBr84.由丙二酸合成 2-苄基丁酸。OOEtO85.由乙酰乙酸乙酯合成86.OHCH2CH3OH87.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.CH390.CHOOHOCH3CHOOHNO291.由CH3CH2CH2CH2Br92.93.BrCOOHCH3CH2CH-CHCH3CH3CH3CH3NO2由CH2CH2CH3CH2CH2CH394NO295.由1-丁烯合成BrCH2CH2CH2CH2Br96.OCH2CH2 CH3OH97.OOCH2 CH3OHCH2CH2CH2CH3OH98.99.10

7、0.CH2ClOCH2CH2 CH3OHCH2ClCH2CH=CH2CH2CH2CH2Cl101102.103.OH(CH3)3CHCCHCH3(不多于四步)BrBrNO2OHBrBr104.(CH3)3CCH2CHCH3BrOH105.由乙炔合成 3,4-二羟基已烷。106.由环戊烷合成CHCH3（其它试剂自选）107.由甲苯合成108.由苯合成H3CCH2CH3BrSO3H109.COCH3110.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。O2NOHNO2112.以苯为原料合成苦味酸()NO2OHNO2113.NO2114.由正丁醇合成 2-丁醇。115

8、.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BrCH3OC2H5CH3C-CH3OH117.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：ClCH2-CH-CH2ClBrCH3CH3-C-CH2CH2CH3119.以丙烯为唯一有机原料合成：OH试题库之五：合成题答案1a.b.CH3d.CH3CH3g.f.COOHCH3ClAlCl3KMnO4Cl2FeCl3ClNO2HNO3H2SO4Br2FeBr3CH3CH3Cl2FeCl3Cl2FeCl3c.BrClClCOOHCl2FeCl3KMnO4NO2e.ClBr2FeBr3HNO3H2SO4

9、H2SO4Br2100FeBr3CH3Cl3FeBrAlCl3Br2HNO3KMnO4H2SO4H2OHNO3180H2SO4CH3COOHBrBrNONO22BrBr2.CH3BrAlBr3HNO3H2SO4Br2FeBr3KMnO4COOHBrNO23CH3COOH(CH3)3CBrAlCl3KMnO4CMe3COOHHNOCH3BrKMnO434.H SOAlBr243NO2OHOK2CrO75.Br2NaNH2OH-2SO46.CH3CH2CH2OHH-HBr170乙醇HBrMe2CHBr-7.CH CH CH OHNa322H+8.CH3CH2CH2CH2OHH2SO4H2O170O

10、HOHOHOH浓H2SO49.浓H2SO41009.100SO3HSO3HOOAgO2/H2O10.CH2=CH2250H2O211.CH CH CH=CHB2H6CH3CH2CH2CH2OH322OH-AgH2OHCN12.CH3CH2OH550COClCOC6H613.AlCl3NaBH4OHO14.H2SO4H2OH-15.方法一：HgSO4NiONaH2OHBrMg15.方法二：干醚液氨H+CH3CH3NBSCH3COCH3H2OMg16.CH2CCH3+H干醚OHCH2ClMgHCHOH3O+CH3CH2CHO17.TM干醚HCl，Zn Cl2CH2ClMgCH3CHOH3O+HCH

11、OTM18.HCl Zn Cl干醚，2MgH3O+CH3CH2BrHCHOTM19.AlCl3干醚KMnO4H2OCH3CH=CHCH3CH3CH-CHCH320.-H+冷OHOH OHH2OHBrMgHCHOCH3CH2CH2CH2OHCH CH CH OH21.322H+干醚H2O22.方法一：CH3CHO+CH3CH2MgBr干醚H+CH3CH2CHCH3OHH2OCH3CH2CHO+CH3MgBr干醚22.方法二：+CH CH32CHCH3HOHOBr2MgH2OCH2CH2OH23.+THFFeClH3H2OHCHOMgCH2CH2OHCH3NBS+24.HTHFOOOH-25.Br

12、CH2(CH2)2CH2COOHH O2H2OMgHCHOHBrCH CH CH OH21.+CH3CH2CH2CH2OHOO322OH干醚+CO2CH3CH2COCH3CO2CH3-H稀OHCH COCH BrNaOEt3226.CH2COCH327.CH3COOHEtOHNaOEtCH3COCH2COOE tCOOE t稀OH-NaOEtBrCH2CH2CH2BrNaOEtCOCH3COCH-HBr-HBr328.CH3COOC2H5NaOEtCH3COCH2COOE tCH3-BrCH3H+HOOCCH-CHCOOEt浓OHNaOEtBrCHCOOEtNaOEt-HBrCH3CH3H2O

13、HCN29.H+NaCNH2OMg30干醚H+CH2OHCNH2OH+H2OH+KMnO431.Na2CrO7KMnO432P2O5H2ONaCNHBr33.方法一：H+MgH2OCO2方法二：HBr干醚H+Br2KMnO4CH3Br34.AlCl3FeEtOH35.HgSO4KMnO4H2SO4H+Na2CrO736H2SO4Ba(OH)237.38.39.40.LiAlH4HBrNaCNMg干醚H2OH+环氧乙烷EtOHH+H2OH+KMnO4PBr3H2OH+CH3COOHHNO3H2SO4Fe+HCl(CH3CO)2O41HBrMg干醚HNO3乙酸H+42CH3CHOH+Na2CrO7

14、NH3Ni43(CH3CO)2OFe44Br245.Fe+HClHNO25C6H5NH2OHHNO3H2SO4Fe+HCl浓HNO3HNO25OH-HNO346H2SO4H2SO4Cl2FeCl3Fe+HClHNO25CuBr-HBr47.(CH3CO)2OHNO3乙酸H2OH+48(CH3CO)2OHNO3乙酐H或OH-+H2OHNO349H2SO4NH4SH乙醇液NaNO2H2SO405H2OHNO3H2SO4Fe+HClBr2NaNO2H2SO4H3PO2+H2O0550HNO(CH3CO)2OBr2FeH2SO4H3O+3H2OH3PO2NaNO251.H2SO4HClH2O180HC

15、l5HNO3Fe+HClBr2NaNO2HClH3PO2+H2O52.H2SO405HNO3Fe+HCl(CH CO)OHNOH2OHNO2NaNO2HBF432353.H2SO4+乙酸H5Cu粉542SO4HHNO3Cl2FeCl3Fe+HClHNO25CuBr-HBr H+/H2ONaOC2H5CH2=CHCH2BrCH3BrNaOC2H555.CH2(COOC2H5)2TMEtONaCH3Br酸式分解CH3COCH2COOE tEtONaCH3CH2CH2CH2Br56.TMNaCNP,Cl2CHCH2 2(CH(CH2 2Br)Br)2 2EtONa水解EtOH57.CH COOHTM

16、3-取代NaOHH2SO4-CO-2NaBr258NaSHNaOHCH3(CH2)3IHNO35960.61.62.63.64.65.66.67.H2SO4PCl3H2NCH3Br2FeCH3COClAlCl3CH3CH2BrAlCl3Zn/HgHClBr2Fe2EtONa CH2I2NaOH HCl或2EtONa BrCH2CH2Br 2EtONaBr(CH2)4BrNa OHH3O+TMEtONa BrCH2CH2COOEtOH-H3O+HNO3H2SO4FeHCl(CH3CO)2OBr2NaNO2HCl5H3PO2H2OHOCH2CH2OHMg乙醚OH3O+EtONaCH3CH2CH2B

17、rEtONaBrCH2CH2CHMe2NaOHEtONaHNOClTM32CH3IH SO24FeCl3Na OH酮式分解Fe+HClHNO25CuBr-HBrTM2EtONaNaOH68.2EtONa HCl BrCH2CH2Br BrCH2CH2BrMgHClCH3COCH3H3O+Ni69.Zn Cl2干醚H2NaOH70.2EtONa(EtOCO)2CH(CH2)3CH(COOEt)2TMBr(CH2)3Br HCl-71.EtONaCH3COClOHTMH2OHNO3HNO372.FeH2SO4OH-H2SO4HCl保护氨基H2SO4CH3COCH2ClOH-73.EtONaTMH2

18、ONa OH74.EtONa(CH3)2CHBrTMHClCH3CH2CH2Br75.CH3CH=CH2HBrNaNH2CH3CH2CH2BrNaNH2CH3CH2CH2BrCH CHTM液氨液氨CHCH2 2(CH(CH2 2Br)Br)2 22EtONa水解76.TM-CO-2NaBr2KMnO4CH3CH2OHEtONaCH CH OH77.TM32+HH酯缩合HNO3Fe(CH3CO)2OH2OHNO378.+H2SO4乙酐HClH或OH-O3OH-79.CHOZn/H2O羟醛缩合-H2OHNO3BaOCu80.250脱羧 脱水EtONaH3O+Na OHEtONa81.TM C2H5

19、Br C2H5BrOEtONaHClNa OH82.COOHOBrCH3CH2CH2MgH3O+Br2CH3CH2CH2CHCH2CH2CH3CrO3TM83.CH3CH2CH2CHO乙酸干醚OHC6H5CH2ClEtONaCH3CH2ClNa OHEtONa84.CH3CH2CHCOOHEtOH HClEtOHCH2C6H5Na OHEtONa2EtONaTM85.BrCH2COOEtCH3IOHOCH2CH386.CrO3NiCH3CH2MgBrH3O+OHH2Et2OCOOH2 EtONaNa OH87.Br(CH2)5BrHClCH3H3O+Cl-CHCOOC2H5Na OH88.Et

20、ONaCH3CCH2CHCOOHEtOHOCH3CrO3HOCH2CH2OHH3O+TM89.保护醛基KMnO4(CH3CO)2OH2O90.HNO3FeH3O+NaNO2HNO3H2SO4HClH2SO4HCl5NaOHHBrNaTM91.CH3CH2CH2Br乙醇Zn-HgCH3CH2COClHNO3H2SO4TM92.HClAlCl3Zn-HgCH3CH2COClBr2CH2CH2CH393.AlCl3FeCl3HClBrHNO94CH3BrAlCl33KMnO4H+H2SO4Br2NaOHNBSTMCH=CHCH CH95.223乙醇高温CH2CH2 CH3HSO4B2H62MgX96

21、.CH3CH2CH+H2O2/OH-H2O/HOHCH CH CH MgXHSO4HBr/H2O2或32+2 NaOH/H2O H2O/HCH2 CH3HSO4CH3CH2MgXB2H697.+H2O/HOHH2O2/OH-CH CH MgXHSO4HBr/H2O2或32+NaOH/H2O H2O/HCH2CH2CH2 CH3HSO4B2H6CH3(CH2)3MgX98.+H2O/HOHH2O2/OH-HSO4CH3(CH2)3MgXHBr/H2O2或/HH2O/CHH+H2OHSO4 NaOHCH2CH2 CH3CH CHMgXB2322699.+H2O2/OH-H2O/HOHHSO4HBr

22、/H2O2或CH3CH2CH2MgX+NaOH/H2O H2O/HHNO3CH3BrKMnO4AlCl3H2SO4H+CH2CH2CH2ClMgH2OOSO2Cl101.干醚OH-H2O/H+Br2Br2HNO3102.FeFeH2SO4OHBr2H2SO4H2ONBS103.170NaOH(CH3)3CH104.(CH)CCH CHCHKOHBr2KOHNaCC3 323CH3H液氨BrPd/CNaNH2NaNH2EtBrEtBrKMnO4CH3CH2CHCHCH2CH3CH CH105.H2OH-冷OHOHH3O+MgCH3CHOCl2TMTM106.干醚光CH3CH3ZnCl2甲苯TMT

23、M107.AlCl3HCl，HCHOCH2ClH2SO4Br2108.TMTMFeBr3HgSO4光CH CNaTM109.Cl2H2OCH2CHCH2CH2CH3CH2Br110.(CH3CH2CH2CH)2-CuLi+CH3CH3CH3CHCH2CH2CH2CH3111.(CH3CH)2-CuLi+CH3CH2CH2CH2BrCH3CH3-Br2HNO3OHHNO3112.TMFeH2SO4H2SO4H2OHNO3Cl2HNO3OH-TM113.FeH2SO4H2SO4H2OH2SO4OH-HBrTM114.CH3CH2CH2CH2OHCH2CH2 CH3H O170CH CH CH MgXHSOB232242H699.H2O/H+H2O2/OH-OH115.OHCH3BrCH CH BrNa OH32TMAlClHSO43或CH3CH2CH2MgXHBr/H2O2+NaOH/H2O H2O/HCH3COCH3MgH3O+HBrBrTM+116.干醚117.+BrTMCl118.CH2=CHCH3Br2CH2-CH-CH2CH2=CHCH2Br2高温室温ClClBrMgCH3CH2CH2BrCH2=CHCH3HBr119.H2O2干醚H3O+TMOH-Na2Cr2O7HBrCH2=CHCH3CH3COCH3