考研有机化学之合成题及答案.doc
：合成题1. 由苯或甲苯及其它无机试剂制备：NO2COOHNO3rg.COOHCH1COOHCH23BBra. b.c.Cl d.e.f.BrClBrNO22ClClBrNOCOOHBr2NO2CH3COOH3CMe3COOH4NO2OHO56. CH3CH2CH2OH CH3CCH7. CHCH CH OH CH CH CH OCH(CH )3223223 28. CHCH CH CH OH CH CH CH(OH)CH32223239. OHOHSO3H10. CH2=CH2 HOCH2CH2OCH2CH2OCH2CH2OH11. CH3CH2CH=CH2 CH3CH2CH2CH2OH12. CH3CH2OH CH3CH(OH)COOH13. COClCO14. 14OOH15. HCCH CH3CH2CH2CH2OH16. 16CHCH33CH2CCH3 OH17. 17CH2CHCH2CH3 OH18. CH2CHCH3OH22219. CH CH CH OH20. 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。OO25. BrCH 2(CH2)2CH2COOH26. 26CO2CH3CH2COCH3OO327. CH COOHCOCH 328. CHCOOC HHOOCCH-CHCOOEt325CH3CH329. OCOOHOH30. CH3CH2CH2BrCH3CH2CH2COOH3 231. (CH ) CHOH(CH3)2CCOOHOOH332. CHOOOCH3OO33(CH3)2C=CH2 (CH3)3CCOOHCOOH34 Br35. HCCH CH3COOC2H5O36. O37. CH3CH2COOH CH3CH2CH2CH2COOH38. CH3COOH CH2(COOC2H5)239. 39CO CHCOOH23OHOOCCH340. NH241. 41NHNH22NO232342. CH CH OHCH CHCHCH32NH243. NH2NHCOCH3NO244. NN45. 45NCHNCH33OHNHNH4622NO2NHNH224748 NH249 50NO2NH2 NO2 OHBrBrNO2BrBrBr51. Br52. CH3CH353. 53NO2BrBrNO254. ClBr55. 由 CH(COOC H )合成 H CCHCOOH225 23CH CH=CH22322556. 由 CH COCH COOC H 合成 CH CH CH CH CH-CH32223COOH57. CH3COOHCOOH32 332 322 3358. CH (CH ) OHCH (CH ) SO (CH ) CHCH359. H CSO NHCH33260. 60CH3CH2Br61. 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。CH363. 用乙酰乙酸乙酯合成 CH3COCH2CH2CH2COOH。64. 64CH365. CH3COCHBr3 O222BrCHCOCHCH CH2OH66. 用乙酰乙酸乙酯合成O67. 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。69. CH3CH COCH33CH CH-C-CH33CH3OH70. 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. 72.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. CHCH=CH ，CHCHCHCH CHCCH CH CH CH32322222376. 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. NH2NO279. CHOOH80. O81. 由乙酰乙酸乙酯合成 3-乙基-2-戊酮。O82. 由丙二酸二乙酯合成COOHOCHO83. 83.Br84. 由丙二酸合成 2-苄基丁酸。O85. 由乙酰乙酸乙酯合成OEtOOHCH CH2386. OH87. 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. OHOCHOCHO90. CH3CH3NO2OH91. 由 CH3CH2CH2CH2BrCH3CH2CH-CHCH 3CH33CH CH392. 由NO2CH2CH2CH393. CH2CH2CH3BrCOOH94. 94NO295. 由1-丁烯合成BrCH2CH2CH2CH2Br96. OCH2CH2 CH3 OHOCH2 CH397. OH98. 98.OCH2CH2CH2CH3 OH99. 99.CH2CH2 CH3 OHO100. CH2ClCH2CH=CH 2101. CH2ClCH2CH2CH2ClBr102. BrNO2OHBr103. BrOH104. (CH3)3CCH2CHCH3Br(CH3)3CHHCCCH3(不多于四步)105. 由乙炔合成 3,4-二羟基已烷。OH106. 由环戊烷合成CHCH3 其它试剂自选107. 由甲苯合成H CCHCH323108. 由苯合成 Br SO3H109. 109.COCH3110. 以铜锂试剂合成 1-苯基-2-甲基戊烷。OH111. 以铜锂试剂合成 2-甲基已烷。112. 以苯为原料合成苦味酸(O2NNO2)OH113. NO2NO2NO2114. 由正丁醇合成 2-丁醇。3115. 由苯酚和两个碳原子及以下的有机物合成CHOC2H5CH3116. 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：CH2-CH-CH 2ClClBrCH3119. 以丙烯为唯一有机原料合成：试题库之五：合成题答案CH3-C-CH2CH2CH3OH1a. CH3ClKMnO4Cl2COOHAlCl3FeCl3ClCH3CH3Cl2 FeCl3Cl2 FeCl3ClClNO2b. HNO3Br2c.H2SO4FeBr3BrCH3d.Cl2KMnO4COOHNO2e. Br2HNO3FeCl3FeBr3H2SO4ClBrCHCOOH3Br2CH ClKMnO4HNO3f. FeBr33AlCl3H2SO4NO2BrCH3H2SO4100Br2FeBr3g. HNO3H OBrBrCH327H2SO4180NO2COOH2. CH3BrHNO3Br2KMnO4BrAlBr3H2SO4FeBr3103. CH3COOH(CH3)3CBrKMnO4AlCl3NO24. CH3BrHNO3KMnO4 AlBr3H2SO4CMe3COOHK2CrO7OHONO25.6. CH CHCH OH H2SO4Br2OH-N-aNH2322170NaMeCHBr乙醇HBrHBr7. CH3CH2CH2OH2-8. CH3CH2CH2CHOH H2SO4H+2170H2OOHOH9. 浓H2SO4SO3HO2 / AgOOH O210010. CH2=CH225011. CHCH CH=CHCH CHCH CH OHB2H6H2O212.32CH CH OH2OH-AgHCNH2O322232550COClCO13. C6H6AlCl314.O NaBH4OH15.H2SO4OH-H215.HgSO4NiO方法二： NaHBrMg方法一：H2O液氨干醚H+CHCH316. 3NBSMgCH COCHH OCHCCH332 +23干醚HOH17.CH2ClHCHOHCl，Zn Cl2HCHOHCl，Zn Cl2MgCH3CH2CHOH3O+干醚TM18.CH2Cl MgCH3CHOH3O+TM干醚CH3CH2BrAlCl3Mg干醚HCHOH3O+19.KMnO4H2O20. CH3CH=CHCH3TMCH CH-CHCH21. CH3CH2CH2OH冷 OH-H+3OH OH3HBrMg干醚HCHOH2OH+CH3CH2CH2CH2OH322. 方法一：CHCHO + CH3CHMgBr 干醚H2OH+CH3CH2CHCH3232322. 方法二：CHCH CHO+ CH干醚H OOHMgBr2H+CH3CH2CHCH3OH23.CH2CH2OHOBr2FeClMgTHFH2O3H+24. CH3NBSMgHCHOH2OCH2CH2OHTHFH+25. BrCH2(CH2)2CH2COOHOH-OOH2OOCO2CH3OCO2CH3CH2COCH326.NaOEtCH3COCH2BrCH2COCH3O稀OH-H+327. CHCOOH EtOHNaOEtCH3COCH2COOEtNaOEt-BrCH2CH2CH2BrHBrNaOEtCOOEt- HBrCOCH稀OH-COCH333228. CH3COOC2H5NaOEtCH COCHCOOEtNaOEtBrC-HCOOEtNaOEt浓OH-H+HBrBrCH3CH3HOOCCH-CHCOOEt29.HCNH2OH+ NaCNH2OCH3CH3H2OH+KMnO430. MgH+干醚Na2CrO7HCNH2O31.CH2OH+32. KMnO4P2O533.HBrNaCNH2O方法一：H+方法二： HBrMgCO2H2O干醚H+CH3BrKMnO4Br234.AlCl3Fe35. HgSO4 H2SO436. Na2CrO7H2SO4 KMnO4Ba(OH)2EtOH H+LiAlH4HBrMg环氧乙烷H2OH+KMnO437.PBr 3NaCNH2OH+EtOHH+干醚38.H2OCH3COOH39.H+40.41.HNO3Fe +HClH2SO4(CH3CO)2OHNO3H+乙酸HBrMgCH3CHO干醚H+Na2CrO7NH3Ni42.43. (CH3CO)2OC6H5NH244. FeFe +HClHNO2 Br2<5OHHNO3H2SO4Fe +HClHNO2<545.HNO3Cl2Fe+HClHNO2CuBr - HBr46. H2SO4浓HNO 3OH -H2SO4 FeCl3<5(CH3CO)2OHNO3H2O47.(CH3CO)2OHNO3乙酐H+或OH -H2O48.HNO3 H2SO4NH4SH乙醇液NaNO2 H2SO405H2O49.HNO3Fe+HClBr2NaNO2 H2SO4H3PO2+H2O50.乙酸H+H2SO4 05H2SO4H3O+Br22180H ONaNOHCl25H3PO2 H2O51. HNO3Fe(CH3CO)2OHNO 3Fe+HClBr 2NaNO2 HClH3PO2+H2O52.H2SO4HClHNO3 H2SO4 Fe+HCl(CH3CO)2OHNO3乙酸H2OH+HNO2<5NaNO2 HBF4Cu粉H2SO4 0553.54. HNO3Cl2Fe+HClHNO2CuBr - HBrH2SO4 FeCl3<5NaOC HH + / H O55.CH2(COOC2H5)22 52TMCH3BrNaOC H2 5CH =CHCH Br22EtONaCH3CH2CH2CH2BrEtONaCH3Br 酸式分解3256. CH COCH COOEtTM57. CHCOOHP,Cl2NaCNEtOHEtONaCH2(CH2Br)2水解TM3 -取代NaOHH2SO 4-2NaBr-CO258. NaSHNaOHCH3(CH2)3IHNO3H2SO4PCl 3H2NCH359.60. Br2CH3COClZn / HgFeAlCl3HCl或 CH3CH2BrBr2AlCl3Fe61. 2EtONa 2 EtONa NaOH BrCH2CH2Br CH2I2 HCl62. 2 EtONaNa OHH3O+TM Br(CH2)4Br63. EtONaOH- BrCH2CH2COOEtHNO3H2SO4Fe HCl(CH3CO)2OBr2H3O+NaNO2HCl5H3PO2 H2O64.HOCH2CH2OHMgOH3O+65.乙醚66. EtONaEtONaNaOHTM CH3CH2CH2BrCH3I67. EtONa酮式分解Na OH HNTOM3Cl2 FeCl3Fe+HClHNO2<5CuBr - HBr2H2SO4 BrCH2CH2CHMe2268.EtONaEtONa NaOH BrCH2CH2Br BrCH2CH2Br HCl69.NiHClMgCH3COCH3H3O+H2Zn Cl2干醚270.EtONa(EtOCO)CH(CH )CH(COOEt) NaOHTM Br(CH2)3Br22 32 HCl71.EtONaCH3COClOH-TMH2O72. HNO3FeH2SO4HNO3OH- H2SO4 HCl保护氨基H2SO4 73. EtONaCH3COCH2ClOH-TMH2OEtONa(CH3)2CHBr74. Na OH HClTM3275. CH CH=CHNaNH2CH3CH2CH2BrNaNH2CH3CH2CH2Br液氨液氨CHCHCH3CH2CH2BrHBrTM2EtONaCH2(CH2Br)2水解76.77. CHCH OH-2NaBrTMKMnO4CH3CH2OHEtONao-CO2TM32HNO3H SO24FeHCl(CH3CO)2OHNO乙酐3H+H2O或OH-78. O3Zn /H2O羟醛缩合OH- H2O79.H+H+酯缩合CHO80. CuHNO3BaO81.250 EtONa C2H5Br EtONa C2H5BrNa OHH3O+脱羧 脱水TMO82.BrO EtONaNa OHHClCOOH83. CH3CH2CH2CHO CH3CH2CH2MgH3O+CH3干醚CH2CH2CHCH2CH2CHTM3CrO3Br2乙酸84.EtONa EtOHOHCH3CH2ClEtONaC6H5CH2Cl Na OHEtOH HClCH3CH2CHCOOH85. EtONa BrCH2COOEtONi H2CrO3OH 2 EtONaNa OHTM CH3ICH CHCH2C6H586. CH3CH2MgBrH3O+2387. 2 EtONa Na OH Br(CH2)5Br HClCH3Et2OOHCOOH88. EtONaCl-CHCOOC2H5Na OHH3O+CH EtOH3CCH O2CHCOOH CH389.TMHOCH CH OH22CrO3H3O+保护醛基90. HNO3KMnO4Fe(CH3CO)2OHNO3H3O+NaNO2H2OH2SO4 HClH2SO4HCl 591. CH92.3CH2CH2BrNaOH乙醇HBrNaTMCH3CH2COClAlCl3HNO3H2SO4Zn-HgHClTM93.94.Zn-HgCH2CH2CH3CH3CH2COClBr2AlCl3FeCl3HClCH3BrHNO3KMnO4BrNBSNaOHBr2AlCl3H2SO4 H+95. CHCH3CH2CH2MgXHSO4 B2H696.2=CHCH2CH3TM乙醇高温CH2CH2 CH3CH3CH2CH2MgXHSO4 HBr / H2O2 H2O /H+H2O2 / OH-OH或 H2O /H+ NaOH / H2O1297. CH3CH2MgXHSO4 B2H6CH2 CH3 H2O / H+H2O2 / OH-OH或 CH3CH2MgXHSO4 HBr / H2O2 H2O /H+ NaOH / H2O1398. CH3(CH2)3MgXHSO4 B2H6CH2CH2CH2 CH3 H2O / H+oH2O2 / OH-OH或 CH3(CH2)3MgXHSO4 HBr / H2O2 H2O /H+ NaOH / H2O99. CH3CH2CH2MgXHSO4 B2H6CH2CH2 CH3 H2O /H+H2O2 / OH-OH或 CH3CH2CH2MgXHSO4 HBr / H2O2HSO4 H2O /H+ NaOH / H2ONaCCHNa / 液氨100.MgO干醚 H2O / H+或CH2CH=CH2 CH2CH=CH2101. Mg OH2OSO2ClBr2FeHNO3H2SO4Br2Fe干醚H2O / H+OH-CH2CH2CH2Cl102.103.OHH SONBSH2OBr224170NaOH104.KOHBr2KOHNa(CH3)3CH(CH3)3CCH2CHCH3Bro液氨CCHCH3NaNH2EtBrNaNH2EtBrPd/C105. CHCHKMnO4CH CH CHCHCH CH106.H2OH- 冷3Cl光2Mg干醚CH3CHOH3O+TM223OHOHCH3CH3107.2ZnCl甲苯TMHC，l HCHOAlCl3CH2ClH SOBr108.242TMFeBr3光109.CHCNaHgSO4TMCl2H2O110. (CH3CH2CH2CH)2-CuL+i CH2BrCH2CHCH2CH2CH3CH3CH3111.(CH3CH)2-CuLi +Br2 FeHNO3 H2SO4 OH-H2OHNO3 H2SO4CH3112.CH3CH2CH2CH2BrCH3CHCH2CH2CH2CH3CH3TM113.Cl2HNO3HNO3OH-TMFeH2SO4 H2SO4 H2O114. CHCH CH CHOHH2SO4HBrOH-TM3222170H2O115. OHCH3BrNa OHCH3CH2BrTMAlCl3116. +117.+BrTMBr MgCH3COCH3H3O+TMHBr干醚Br223118. CH =CHCH高温CH2=CHCH2BrCH2-CH-CH2Cl2室温ClClBr119. CH2=CHCH3H2O2干醚CH3CH2CH2BrHBrMgHBrOH-Na2Cr2O7H3O+TMCH =CHCHCH COCH2333
