《有机化学》课程教学资源_试题库_题库二_试题库2-5：合成题答案

试题库之五：合成题答案 1. 000 13 0器 。品 COOH NO .0 M OH 8ou0o0aH二 H 1o Gtroro e

试题库之五：合成题答案 1． 3． a. CH3Cl AlCl3 KMnO4 Cl2 FeCl3 COOH Cl NO2 Br b. Br2 FeBr3 HNO3 H2SO4 CH3 Cl Cl c. Cl2 CH3 Cl2 FeCl3 FeCl3 COOH Cl d. Cl2 KMnO4 CH3 FeCl3 NO2 Br e. Br2 FeBr3 HNO3 H2SO4 COOH Br NO2 f. CH3Cl AlCl3 B KMnO4 r2 FeBr3 HNO3 H2SO4 CH3 CH3 NO2 Br Br g. Br2 FeBr3 HNO3 H2SO4 CH3 H2SO4 100℃ 180℃ H2O COOH NO2 KMnO4 Br2 FeBr3 HNO3 H2SO4 CH3Br AlBr3 Br 2. CH3 COOH CMe3 AlCl3 (CH3 )3CBr KMnO4 CH3CH2CH2OH H2SO4 Br2 OH - - HBr HBr NaNH2 170℃ 乙醇 - 6. CH3CH2CH2OH Na Me2CHBr 7. COOH NO2 CH3B KMnO4 r AlBr3 HNO3 H2SO4 4. OH O 5 K2CrO7 . CH3CH2CH2CH2OH H2SO4 H + 170℃ H2O 8. OH OH SO3H 浓H2SO4 100℃ 9. CH2=CH2 O2 /Ag 250℃ H2O O O 10. OH OH SO3H 浓H2SO4 100℃ 9

11.CH,CH.CH-CH CHCH CHCHOH 2o00如 no"00 14Oo些○oH CH3 16"画0ot80t OH n=台a心m 18器m匹w H 19,⑦4出MH0HgTw 20.CH,GHGH GLGIGGI 21.GHCNOIOUOLOOHOH 2.方i达-，aH,Ci0+CH,CH2MgBr0 CHaCH2CHCH 2.方i法=，CH,CH,Ci0+CHMg8r王9CH,CH98,CH OH 3O急÷△，ooor 24◇o6s÷iao9◇ar,aom 25.BCH:(CH2):CH.COOH 00 CH CH-CH2CH2OH CH2COCH3 26.● 4Le4 ccmc00,4世 27.CH.COOHCHgCOCH2COOE 鱼2ane◇u◇0

CH3CH2CH=CH2 B2H6 H2O2 OH 11. - CH3CH2CH2CH2OH CH3CH2OH Ag 550℃ HCN H2O 12. C6H6 AlCl3 COCl CO 13. O OH NaBH4 14. H2SO4 方法一：HgSO4 OH - △ Ni H2 15. O 方法二： Na 液氨 HBr Mg 干醚 H2O H + 15. CH3 CH2 C CH3 OH CH3 NBS Mg 干醚 CH3COCH3 H2O H + 16. CH3CH=CHCH 3 H2O H + KMnO4 OH - 冷 CH3CH-CHCH 3 OH OH 20. HCHO CH3CH2CH2OH Mg 干醚 H2O H + HBr 21. CH3CH2CH2CH2OH HCl Zn Cl2 干醚 Mg HCHO CH3CH2CHO ， CH2Cl H3O + 17. TM HCl Zn Cl2 干醚 HCHO Mg ， CH2Cl H3O + TM CH3CHO 18. 干醚 Mg HCHO H3O + TM CH3CH2Br AlCl3 19. HCHO CH3CH2CH2OH Mg 干醚 H2O H + HBr 21. CH3CH2CH2CH2OH 干醚 H2O H + CH3CH2CHCH3 OH 方法一：CH CH3CH2MgBr 22. 3CHO + 干醚 H2O H + CH3CH2CHCH3 OH CH CH3MgBr 22. 方法二： 3CH2CHO+ Br2 FeCl3 Mg THF O H2O CH2CH2OH H 23. + NBS Mg THF CH3 HCHO H2O CH2CH2OH H 24. + H2O OH - BrCH2 (CH2 )2CH2COOH △ O O 25. OH - 稀 O CO2CH3 O CH2COCH3 NaOEt CH3COCH2Br O CO2CH3 CH2COCH3 H + △ 26. CH3COOH EtOH NaOEt 27. CH3COCH2COOEt N COCH3 aOEt BrCH2CH2CH2Br - HBr NaOEt -HBr COCH3 COOEt 稀OH -

28.CHaCOOC2H NaOCHaCOCH2COOEt CH3 NORNB HOOCCH-CHCOOE CHCH3 29.℃9 NCN Ho H 32.Kho4P20, 33.方法-上B出0 ®普0品 34器0÷ 37山区0Z904 38.Pe90 39.9出，co04 H 40e2a4 41.(CHCOnO HNO 乙酸 42.8青C0LeC0学 43.(CHconQ 4.e+HGHw9、CsN Br2 <5C 45受a2 yoH 46.0◆四，2品业2e电地 <5℃

30 ． 32 ． 36 ． 41 ． 42 ． 43 ． 44 ． 46 ． C H3C O O C2H5NaO Et C H3C O C H2C O O Et NaOEt BrCHCOOEt HBr NaOEt H O O C C H-C H C O O Et CH3CH3 CH3 - 浓OH- H+ BrCH3 28. HCN H2OH 29. + NaCN H2OH ① + ② Mg 干醚 CH2O H2OH+ KMnO4 Na2CrO7 H2OH+ HCN 31. KMnO4 P2O5 △ 方法一： 方法二： Mg 干醚 H2OH+ HBr NaCN HBr CO2 H2OH+ 33. CH3Br KMnO4 AlCl3 Br2 Fe 34. H2SO4 HgSO4 KMnO4 EtOH H+ 35. H2SO4 Na2CrO7 △ △ Ba(OH)2 KMnO4 H+ LiAlH4 HBr Mg 干醚 环氧乙烷 H2O 37. EtOH H+ PBr3 NaCN H2O H 38 + . CH3COOH H+ H2O 39. H2SO4 HNO3 Fe +HCl 40. H HNO + 3 (CH3CO)2O 乙酸 H HBr M + Na2CrO7 g 干醚 CH3CHO NH3 Ni (CH3CO)2O FeBr2 Fe +HCl HNO2 <5℃ C6H5NH2 +HCl H2SO4 HNO3 OH Fe <5℃ 45 HNO2 . H2SO4 OH - 浓HNO3 FeCl3 HBr <5℃HNO2 HNO3 H2SO4 △ C Fe+HCl CuBr - l2

47.co49e 4.4 从器 △ 0.器出0 05℃ 22四40心0 05℃ 532aw42鹊20画 Cu粉 542e凸9，e8 5.qH(c0OC,HhN04a些0c49 -CHCHB H产9TM 56.cH,coCH,COOELO出CHCHCHCHB,EION CHr分TM auow9rag女w -2NaBr 58.NaSt NaDl!CH(CH)N 59.h04P0w①0 60.4a HCI 或地 62oL出0w 63 O 4。品o心以器盼 66心山M 61a器之山，c地

48 ． 49 ． 50 ． 54 ． 58 ． 59 ． ( C H3 C O )2 O H N O3 H2 O H 乙 酸 + 4 7. (CH3 C O )2 O H N O3 乙 酐 H2 O H+ O H 或 - H N O 3 H 2 S O 4 NH 4 S H N aN O 2 H 2 S O 4 H 2 O △ 乙 醇 液 0 ~ 5 ℃ △ HN O 3 H2 S O4 △ F e +H Cl Br 2 N aN O 2 H2 S O4 0 ~ 5 ℃ H 3 P O2 + H2 O HN O 3 H2 S O4 △ F e +H Cl Br2 N aN O 2 0 ~ 5 ℃H Cl H 3 P O2 + H2 O 5 2. F e Cl3 H Br <5℃HNO2 HN O 3 H2 S O4 △ C F e +H Cl C u Br - l2 <5℃ (CH3CO)2O HNO3 HNO2 乙酸 NaNO2 HNO3 H2SO4 △ Fe+HCl H B F4 Cu粉 H2OH+ 53. H2SO4 HNO3 Fe HCl Br H2SO4 2 △ (CH3CO)2O H3O+ 180℃H2O NaN O2 HCl ＜5℃ H3P O2 H2O 51. FeCl3 HBr <5℃HNO2 HNO3 H2SO4 △ C Fe+HCl CuBr - l2 NaOC2H5 △ H + / H2O CH2(COOC2H5)2 TM CH3Br NaOC2H5 CH2=CHCH2Br 55. CH3COCH2COOEt 56. EtONa CH3CH2CH2CH2Br EtONa CH3Br 酸式分解 TM CH3COOH P,Cl 2 NaCN EtOH α NaOH H2SO4 -取代 EtONa CH2(CH2Br)2 -2NaBr △ -CO2 水解 57. TM NaSH NaOH CH3(CH2)3I HNO3 H2SO4 PCl3 H2N CH3 Br2 Fe CH3CH2Br AlCl3 Br2 Fe CH3COCl AlCl3 Zn / Hg HCl 60. 或① EtONa NaOH ② BrCH2CH2Br 2 ① EtONa ② CH2I2 2 ①② HCl △ 61. ① EtONa ② BrCH2CH2COOEt OH- 63. H2SO4 △ HNO3 Fe HCl (CH3CO)2O Br2 H3O+ NaNO2 HCl ＜5℃ H3PO2 H2O 64. H3O+ ① TM ② 2 Br(CH2)4Br 62. EtONa Na OH Mg H3O HOCH + 2CH2OH 乙醚 65. O ① EtONa NaOH ②CH3CH2CH2Br ①EtONa ②CH3I 66. TM ① TM ②BrCH2CH2CHMe2 EtONa Na OH 酮式分解 67

RGICILB RUCIUB 69.出品尝coaL0 71coa,恶w HNO 73.BON CHCOCH-CI0 TM 4.ea。→ 75.cAF6e→cm0 aa尝aaa尝a 62心a女m -2NaBr TICICILO器m 22s0☆Oc0 9.℃00 80.101 飘发展水 82.DEONa NaOI HCLC00M 8 83CCILCICHO CHCCME O CCILOLGCLOLGI CO TM 干壁 4aa6a0。一aaaa OH 0 860e0♂a→9" 7漂，0 应鸟云产gao

① EtONa NaOH ② BrCH2CH2Br 2 ① ② HCl ① EtONa ② BrCH2CH2Br 2 △ 68. H2 Ni HCl Zn Cl2 干醚 Mg CH3COCH3 H3O + 69. ① EtONa ② Br(CH2 )3Br 2 (EtOCO)2CH(CH2 )3CH(COOEt)2 ① NaOH ② HCl △ 70. TM EtONa CH3COCl TM OH - H2O 71. H2SO4 △ HNO3 Fe HCl H2SO4 保护氨基 H2SO4 △ HNO3 OH - 72. EtONa CH3COCH2Cl TM OH - H2O 73. EtONa (CH3 )2CHBr TM ① Na OH ② HCl △ 74. CH3CH=CH2 HBr CH3CH2CH2Br CH≡CH 液氨 NaNH2 CH3CH2CH2Br 液氨 NaNH2 CH3CH2CH2Br TM 75. (CH3CO)2O HNO3 乙酐 H2O H + OH H △ 或 - 2SO4 HNO3 Fe HCl 78. EtONa CH2 (CH2Br)2 -2NaBr △ -CO2 水解 TM 2 76. EtONa CH3CH2OH TM KMnO4 H + CH3CH2OH H + 酯缩合 77. CHO ① O3 ②Zn /H2O OH - 羟醛缩合 △ -H2O 79. Cu 250℃ HNO3 BaO △ 脱羧 脱水 80. ① ② C2H5Br EtONa ① ② C2H5Br EtONa Na OH △ H3O + △ 81. TM Na OH O Br ① EtONa ② HCl △ O 82. COOH CH3CH2CH2CHO 干醚 CH3CH2CH2Mg H3O + CH3CH2CH2CHCH2CH2CH3 OH Br C 2 rO3 乙酸 83. TM ① ② BrCH2COOEt EtONa ① ② 2 CH3 I EtONa Na OH 85. TM EtONa CH3CH2Cl EtOH EtONa EtOH C6H5CH2Cl ① ② HCl Na OH △ CH3CH2CHCOOH CH2C6H5 84. OH CH2CH3 H OH 2 Ni CrO3 O CH3CH2MgBr Et2O H3O + 86. COOH ① ② 2 Br(CH2 )5Br EtONa ① HCl Na OH ② △ 87. EtONa EtOH Cl-CHCOOC2H5 CH3 Na OH △ H3O + △ CH3CCH2CHCOOH O CH3 88

8 occo,CO、HC、TM 保基 0品心0 91TM 2☑eeo00.s042m g⊙0品oco AICl Br “赠京学 94. CHCH CHMX HSO CHCH CH 96. ①BHe ②H0/ HBr H2Oz OH 雪S业巴冷 -OH △ 98①CHCH)MgX HSO①B2L。 CH-CH-CH CH ②01 或①CH(CH)MX HSO,m,.0 ②H0/H a②NOH/H,0 99. o◇ BL ②H01r OH H 1m普品验40waad 12⊙器 103.了"8品

94． HOCH2CH2OH 保护醛基 CrO3 H3O + 89. TM H2SO4 △ HNO3 KMnO4 Fe HCl (CH3CO)2O H2SO4 HNO3 H3O + NaNO2 HCl ＜5℃ H2O 90. CH3CH2CH2Br NaOH 乙醇 HBr Na 91. TM CH3CH2COCl TM AlCl3 △ HNO3 H2SO4 Zn-Hg HCl 92. CH2CH2CH3 Br CH3CH2COCl AlCl3 Br2 FeCl3 Zn-Hg HCl 93. CH3Br AlCl3 H2SO4 △ HNO3 KMnO4 H + CH3Br AlCl3 H2SO4 △ HNO3 KMnO4 H + CH2=CHCH2CH3 TM NBS NaOH Br2 乙醇 高温 95. △ B2H6 H2O2 OH - CH2CH2 CH3 OH HSO4 H2O H + HBr NaOH ①CH3CH2CH2MgX ② / ① ② / △ HSO4 H2O H + ①CH3CH2CH2MgX ② / ② /H2O 或 ① / H2O2 96. △ B2H6 H2O2 OH - CH2 CH3 OH HSO4 H2O H + HBr NaOH ① CH3CH2MgX ② / ① ② / △ HSO4 H2O H + ①CH3CH2MgX ② / ② /H2O 或 ① / H2O2 97. △ B2H6 H2O2 OH - CH2CH2CH2 CH3 OH HSO4 H2O H + HBr NaOH CH3 (CH2 ) ① 3MgX ② / ① ② / △ HSO4 H2O H + ① ② / ② /H2O 或 CH3 (CH2 )3MgX ① / H2O2 98. △ B2H6 H2O2 O H- HSO4 H2O H + HBr NaOH ①CH3CH2CH2MgX ② / ① ② / △ HSO4 H2O H + ①CH3CH2CH2MgX ② / ② /H2O 或 ① / H2O2 CH2CH2 CH3 OH 99. H2SO4 Fe Br2 HNO3 Fe Br2 102. H2SO4 NBS OH 170℃ H2O NaOH Br2 103. Mg CH2CH2CH2Cl H2O H + ① O H2O 干醚 ② / OH - SO2Cl 101

104eweeeot2gaerc=6 100o1出m等曾o0g8eo 16Q完常4aogm 1m时斯m CH2CI ◇典m 109盖台48w 110.(CH,c,C,CHCM+○-chm→{○-CH.CHCH.CH,CH CH 111.(CH;CH)-CuLi CH,CH2CH2CH2Br->CH;CHCH2CH2CH2CH3 CH3 1B丹220w 114.CH.CH.CH.CIOM TM 115.OH CHBr NaOH CHCHB TM AICh 6《+。○告a@N n《+LA一M aaia0aaaa台gg 119.C-CCH CCHI.CHaB CH2-CHCHO NaCO CH.COCHJ HOTM 99 OCHCH,CM 2H0/H 品o〔丫CHaCH:CHs OH 或CHCH-CH-MgX、HsO,HBr0, ②H01H △ ②NaOH/H20

109. 116. 117. 118. 119. Br2 (CH3)3CCH2CHCH3 Br (CH3)3C C H C H CH3 KOH △ KOH △ Na 液氨 104. CH≡CH NaNH2 EtBr NaNH2 EtBr Pd/C H2 KMnO4 OH - 冷 CH3CH2CHCHCH2CH3 OHOH 105. Cl2 光 Mg 干醚 CH3CHO H3O + 106. TM TM CH3 ZnCl2 HC，l HCHO 甲苯 CH3 CH2Cl AlCl3 107. TM H2SO4 Br2 FeBr3 108. CH≡CNa TM HgSO4 Cl2 H2O 光 (CH3CH2CH2CH)2 -CuL+i CH2Br CH3 CH2CHCH2CH2CH3 CH3 110. (CH3CH)2 -CuLi + CH3CH2CH2CH2Br CH3 CH3CHCH2CH2CH2CH3 CH3 111. Br2 Fe H2SO4 △ HNO3 H2O OH - H2SO4 HNO3 112. TM Cl2 Fe H2SO4 △ HNO3 H2O OH - TM H2SO4 HNO3 △ 113. H2O OH H - 2SO4 CH3CH2CH2CH2OH 170℃ HBr 114. TM CH3CH2Br OH CH3Br AlCl3 Na OH 115. TM + HBr △ Br 干醚 Mg CH3COCH 3 H3O + TM + Br △ TM CH2=CHCH 3 Br2 高温 CH2=CHCH 2Br Cl2 室温 CH2 -CH-CH 2 Cl Cl Br CH2=CHCH 3 HBr CH3CH2CH2Br H2O2 干醚 Mg CH2=CHCH 3 HBr OH - Na2Cr2O7 CH3COCH3 H3O + TM △ B2H6 H2O2 O H- HSO4 H2O H + HBr NaOH ①CH3CH2CH2MgX ② / ① ② / △ HSO4 H2O H + ①CH3CH2CH2MgX ② / ② /H2O 或 ① / H2O2 CH2CH2 CH3 OH 99