有机化学试题库五——合成题及解答

1、12.3.4.5.6.7.8.9.10111213141516试题库五一一合成题及解答由苯或甲苯及其它无机试剂制备:c.ClCH3ClCle.BrCOOH NO 2Br*COOHCH30OH1#CH3CH2CH2OH CH3C 三 CHCH3CH2CH2OH CH3CH2CH2OCH2H 3)2CH3CH2CH2CH2OH CH3CH2CH(OH)CH 3OHOH#SO3HCH2=CH2HOCH2CH2OCH2CH2OCH2CH2OH#.CH3CH2CH=CH2 CH3CH2CH2CH2OH.CH3CH2OH CH3CH(OH)COOH#HC 三 CH CH3CH2CH2CH2OH#CH2一

2、CCH3CH 3OH#17一 _ ch2chch2ch3 OH18.：_ CH2CHCH3 OH2#BrCH2(CH2)2CH2COOHCH 3COOH lCOCH 326.29.OCOOHOH19.'J' _ CH2CH2CH2OH20. CH3CH=CHCH3 CH3CH-CHCHOOH OH21. 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。25.27.28. CH3COOC2H5HOOCCH-CHCOOEtCH3CH3#31.32.CH3

3、O34.30.CH 3CH 2CH 2Br CH 3CH 2CH 2COOH(CH 3)2CHOH (CH 3)2CCOOHOH33. (CH3)2C=CH2 (CH3)3CCOOHCOOHBr#HC三CH f CH3COOC2H535.36.37.38.39.40.41.42.43.44.45.46.47.48.49.50.3#CH3CH2COOH f CH3CH2CH2CH2COOHCH3COOH f CH2（COOC2H5）2CO 2CH 3NH2COOHOOCCHOH#1.1. NH2no2CH3CH2OH CH3CHCH 2CH3NH2:-J NHCOCH#nh2nh26-NO 2n

4、h26'NH22 NO2BrBr4CH 3NO 2BrBr Br 亠丨.丨CH3BrBr51.52.53.54.55.56.57.58.59.60.61.62.63.64.65.66.67.68.5#由 CH2（COOC2H5）2 合成HbC-CHCOOHCH2CH=CH2由 CH3COCH2COOc2H5 合成 CH3CH2CH2CH2CH-CH 3/COOHCH3COOHCH 3（CH 2）3OH* CH3 （CH2）3SO 2（CH 2）3CH 3#用丙二酸二乙酯合成1,3-环戊二甲酸。用丙二酸二乙酯合成1,1-环戊二甲酸。用乙酰乙酸乙酯合成CH3COCH2CH2CH2COOH。

5、#ch3ch3BrCHgCOCHzBr CH3COCH2CH2CH2OH用乙酰乙酸乙酯合成用乙酰乙酸乙酯合成用丙二酸二乙酯合成1 ,CH369 - CH3COCH3 » CH3CH-C-CH 3CH3OH70.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NH272. NO273. 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O75. CH3CH=CH2, CH CH CH3CH2CH2CCH2CH2CH2CH376. 由丙二酸二乙酯合成环丁基甲酸。NH2NO 2CHO77. 由乙醇合成乙酰乙酸乙酯78.79. 111OH80. I J I /

6、 O81. 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5.COOHO87.用丙二酸二乙酯合成环已基甲酸6#OCHO88. 用乙酰乙酸乙酯合成2-甲基-4-戊酮酸OH89. 门CHO#90.NO27#91.由 CH3CH2CH2CH2BrCH3CH2CH-CHCH 3CH311CH3CH3#92.CH2CH2CH393.CH2CH2CH3COOH#96.97.98.99.OHch2ch2ch3100.CH2CIch2ch=ch 2101.102.103.IJO-BrBr94. 1|_no295. 由 1-丁烯合成 BrCH2CH2CH2CH2BrxxvCH2CH2 CH3OH

7、ch2ch2ch2ch3OH#OH#104.(CH 3)3CCH 2CHCH 3(CH3)3C：c二cH(不多于四步)BrCH3#105. 由乙炔合成3,4-二羟基已烷。OH由环戊烷合成| _chch3 （其它试剂自选）8#106. 由甲苯合成H3C O ch2ch#108.由苯合成1 BrSO3H109. 1 ' 一-|COCH 3110.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NO 2OHO2N - 1 ) NO2NO2#114. 由正丁醇合成2-丁醇。CH3-.- OC2H5115. 由苯酚和两个碳原子及以下的有机物合

8、成CH3116.五个C原子以下的有机物合成 C-CH3OH117. 以不多于4个C的有机物为原料合成：Br118. 以丙烯为原料合成：CH扌的2CH3CH3-C-CH2CH2CH3IOHCl Cl Br119. 以丙烯为唯一有机原料合成：试题库之五：合成题答案#b.HNO 3Br2no2H2SO4FeBr3UkBrCH3.Ai.Cl2KMnO 4COOHd.FeCl3CH3ClBr2CH3CIKMnO4f f.FeBr3AICI3NO2Br?HNO 3e.FeBr 3H2SO4BrCOOH1HNO 3&NO2H2SO4Br9CH3g.CH3H2SO4100 CBr2FeBr 3HNO

9、3H2SO 4H2OBr人八八” 180 CNO2Br10#2.COOHCH3Brhno3Br2KMnO 4BrAlBr 3H2SO4FeBr3V1NO2COOH3.4.OCH3BrHNO3KMnO 4AlBr 3H2SO4NO25.H2SO4Br2CH3CH2CH2OH 170C 6.OH乙醇NaNH2-HBrCH3(CH3)3CBr KMnO 4 A*CMe3COOH#-HBr7. CH3CH2CH2OH Na. Me2CHBr .8. CH3CH2CH2CH2OH ：驚 H10.9.OH#R q HHo O11. CH3CH2CH=CH 22 6 A OH-2，CH3CH2CH2CH2O

10、H12. CH3CH2OH550 C#15.、.H2SO4CI_TH?方法一：OHH2HgSO4Ni#15.方法二液N氨HBr干醚H2OH+1116.17.18.CH3NBS Mg CH3COCH 3 H2O+干醚HCH 3CH2CIHCHOMgHCI Zn Cl 2 CH2CIHCHO_&HCI Zn Cl2CH3CH2CHOCH 2 C CH 3OHH3O+ TMMgch3choh3o+干醚TM1219.OCH3CH2BrMg HCHOH3O+Aici： A 干*20. CH3CH=CHCH 3H2°. CH3CH-CHCH 3冷 OHH1OH OH21. CH3CH2C

11、H2OH HBr.干醚 HCHO * 日眷.ch 3CH 2CH 2CH 2OH干醚 h2o22. 方法一：CH3CHO + CH 3CH 2MgBr 醚»h* CH3CH2CHCH 322.方法二：CH3CH2CHO+ CHsMgBr 干醚 日眷 ch3CHOCHCH 3OH23.MgTHF24.NBSMgTHFHCHOH2OH+25.26.BrCH 2(CH2)2CH2COOH2O. ch3ch2ch2ohII /CO2CH3NaOEtOH-H2OHBr Mg干醚CH3COCH 2BrCH2COCH 327. CH3COOH EtOH NaOEt CH3COCH 2COOEtCO

12、OEt 沖“ 稀OHCOCH 3NaOEt BrCH2CH2CH2Br NaOEt-HBr-HBr28.CH 3COOC 2H5NaOEt CH 3COCH 2COOEtCH3NaOEt- BrCHCOOEt j. NaOEt- BrCHL 浓OH* H+.HBrHOOCCH-CHCOOEtCH3CH329.HCNH2O30.31. NaCNH2(+H H2O _ KMnO 4 -H +干醚CH 2。Na2CrO7HCNH2OH+KMnO4P2。5方法一:HBr NaCNH2OH +方法二：HBrMgCO2H2O干醚H+Br2FeCH3BrKMnO 4AAICI 3Hgs。4 KMnO 4Et

13、OHH2SO4H+Na2CrO7Ba(OH)2- =H2SO 4 LiAIH 4 HBr Mg环氧乙烷H2O KMnO 44干醚H+PBr3NaCN H2OEtOHAA + +HHH2OCH3COOHHHNO3 Fe + HCIH2SO 4(CH3CO)2O HNO3 h +32.33.34.35.36.37.38.39.40.41.42.43.44.45.46.47.48.49.50.51.52.乙酸13#HBr MgCH3CHOH+ Na2CrO7NH3#Ni(CH3CO)2OFe 尸 Fe +HC|» _HNO 2C6H5NH2Bs<5 CHN°3Fe +HCI

14、 HNO2H2 SO4H2SO4 浓 HNO3 ohooOH<5 CHNO3 CI2 Fe+HCI FeCI3h2so4HN。2 CuBr -HBr<5C(CH3CO)2。HNO3乙酸H2。#(CH3CO)2。HNO3H2O乙酐 H 或OH -HNO3 NH4SH NaNO2 H2SO4H2OH2SO4A 乙醇液05CHNO 3 Fe+HCIBr2 NaNO2H2SO4 H3PO2+H2OH2SO4 05CHNO3 FeH2SO4HCI(CH3C62。H2SO4H2。180CNaNO2HCI v 5CH3PO2H2O#HNO 3 Fe+HCI B2NaNO2 HCI H3PO2+H

15、2OH2SO4 05 C1453.”驚3»严+旳（CH3CO）2Ohno3乙酸H2OHNO2<5 CNaNO2 HBF4Cu粉15HN。2CuBr -HBr<5 C54 HNO3- Cl2 Fe+HCI .塚04 J F】Cl 3 L*#55. CH2(COOC2H5)2NaOC2H5CH3BrNaOC2H5 CH2=CHCH2Bra*H + /H2OTM#56. CH3COCH 2COOEt EtONa CH 3CH2CH2CH2BrEtONa CH3Br 酸式分解 TM57. CH3COOHP,CI2NaCNa -取代 NaOHEtOH EtONaCH2(CH2Br)

16、2水解H2SO4-2NaBr -CO2 TM58. NaSH NaOHCH3(CH2)3IHNO359.H2SO4 PCl3 H2NcH3 60.Br2 FeCH3COCI Zn / HgAlCl 3HClCHbCHqBfB2AlCl 3Fe61. 2EtONa 2 EtONa 严 NaOH BrCH2CH2Br CH2I2 HCl62.2 EtONa 竺 OH 出。+_ Br(CH 2)4BrTM63. EtONa BrCH2CH2COOEtOH-#64.HNO3Fe(CH3CO)2。Br2H3O+NaNO2 H3PO2H2SO4 HClHCl v 5 CH2O#65.HOCH2CH2OHM

17、g乙醚 EtONaNaOH CH3CH2CH2Br CH3ITM67.68. EtONa Na OH BrCH 2CH2CHMe2酮式分解 HNOl3Cl2 Fe+HClh2SO4 FeCl 3 2EtONa 2EtONa NaOH BrCH2CH2Br BrCH 2CH2Br HCl HNO 2 CuBr -HBr<5 C69.70.71.Ni HCl MgCH3COCH3 H3O+H2Zn Cl2 干醚 2 EtONa NaOH £伪2朋：(Et0C0)2CH(CH2)3CH(COOEt)2 HCl » Ft。Na_CH3COCIOHl tmH2OTM72. HN

18、O FeH2S6 严HN°3 - OH-h2SO4 HCl 保护氨基H2SO4 73.EtONaCH38CH2CIH2OTM1674.EtONa(CH3)2CHBr Na OHHCIATMHBr75. CH3CH=CH2 CH3CH2CH2BrNaNH2CH3CH2CH2BrNaNH2CH3CH2CH2Br液氨液氨76 2EtONaCH2(CH2Br)2 水解 “76 TM-2NaBr -CO277.CH3CH2OHKMnO4 acH3CH2OHH+EtONa TM酯缩合78.HNO 3FeH2SO4 HCl79.。3OHCHO80.81.Zn /H2o羟醛缩合 -H2oCu HNO

19、3 BaO250 C脱羧脱水 Eg » EtONa 一 NaOH _ H 3。- TM C2H5Br _ TM C2H5Br82.aBrOCOOHCH3CH2CH2Mg83.CH3CH2CH2CHO 322干醚H3O » CH3CH2CH2CHCH 2CH2CH3c° 引2 OH乙酸TMEtONa84. EtOHCH3CH2ClEtONaC6H5CH2Cl Na OHEtOH HClCH3CH2CHCOOHCH2C6H585. EtONa BrCH2COOEt 2 EtONa Na OH TM CH3I86.OHNiH2OCrO3CH3CH2MgBrEt2OCH2

20、CH3OH87. 2 EtONa Na OH Br(CH 2)5Br HCl COOHCH388.EtONa 尸 Cl-CHCOOC 2H5 “ Na OH EtOHH3O+-3ch3cch2chcooh3II 21O CH3HOCH2CH2OHCrO3H3O+ tm保护醛基90 HNO 3” KMnO 4 尸 Fe 严(CH 38)2。_ HNO 3H30： " h2so489.H 2SO 4 HClNaOH HBr91. CH3CH2CH2Br 乙醇HBrNaNO2H2OHCl v 5C92.AlCl3Na TMCH3CH2COCIHNO 3 H2SO4 Zn-Hg tmHClC

21、H3CH2COCIAlCl 3Br2FeCl3Zn-HgHClCH2CH2CH393.Br1894CH3Br _ HNO3 KMnO 4AlCl3H2SO495. CH 2=CHCH 2CH3 NBS .乙醇H .高1温.TM96. CH3CH2CH2MgXHSO4 B2H6 H2O / HH2O2/OH-ch2ch2 ch3OH97.98.或CH3CH2CH2MgXHSO 4 HBr / H2O2 H2O / H+ NaOH /h2o CH3CH2MgXHSO4 B2H6 H2O / H+H2O2/OH-或 CHgCHzMgXHSO4 HBr / HqO? H2O / H+ NaOH /h2OCH2CH3OH CH3(CH2)3MgXHSO4 B2H6CH2CH2CH2 CH3 H2O / H+ *H2°2/OH_ OH或 CH3(CH2)3MgXHSO4 HBr / H2O2 H2O / H+ NaOH /h2O100.干醚X+ HSO或 NaC老H101-干醚X+OH-Br2HNO 3CH2CH=CH 2Na /液氨H2OSO2ClCH2CH=CH 2ch