有機化學(xué)試題庫五——合成題及解答

1、12.3.4.5.6.7.8.9.10111213141516試題庫五一一合成題及解答由苯或甲苯及其它無機試劑制備:CH3COOH1NO 21c.-Cld. e.6TTCl1ClBrCOOHCH3BrNO 2CH3COOH 一CH3CH2CH2OH CH3C 三 CHCH3CH2CH2OH CH3CH2CH2OCH(CH 3)2CH3CH2CH2CH2OH CH3CH2CH(OH)CH 3OHOHSO3HCH2=CH2HOCH2CH2OCH2CH2OCH2CH2OH.CH3CH2CH=CH2 CH3CH2CH2CH2OH.CH3CH2OH CH3CH(OH)COOH.弋CO 1HC 三 CH

2、CH3CH2CH2CH2OH17 I | _ ch2chch2ch3Oh18.勺鄉(xiāng) ch2chch3 Oh何 I -I _ CH2CH2CH2OH20. CH3CH=CHCH3 CHsCH-CHCHOOH OH21. CH3CH2CH2OH CH3CH2CH2CH2OH22. 寫出由相應(yīng)的羰基化合物及格氏試劑合成 2-丁醇的兩條路線23. 由苯合成2-苯基乙醇。24. 由甲苯合成2-苯基乙醇。25.BrCH2(CH2)2CH2COOH26.OCH2COCH 3CH3COOHCOCH 329.COOHOH31.32.30.CH 3CH2CH2Br- CH3CH2CH2COOH27.28. CH3

3、COOC 2H5A HOOCCH-CHCOOEtCH3CH3COOH33. (CH3)2C=CH2 (CH3)3CCOOH34.HC三CH f CH3COOC2H5OO35.36.37.38.39.40.41.42.43.44.45.46.47.48.49.50.CH3CH2COOH f CH3CH2CH2CH2COOHCH3COOH f CH2(COOC2H5)2CO 2CH 3OHNH2COOHOOCCH 333CHNH26-NH26'NO2nh2/Inh2NO 2NO 2ABrNO 251.52.53.54.55.56.57.58.59.60.61.62.63.64.65.66.

4、67.68.CH3COOH CH3CH 23SO2CH23C H3Cl OkBr由 CH2COOC2H52 合成H3C CHCOOHch2ch=ch2由 CH3COCH2COOC2H5 合成 CH3CH2CH2CH2CH-CH 3COOHCOOHCH3CH23OH用丙二酸二乙酯合成1,3-環(huán)戊二甲酸。用丙二酸二乙酯合成1,1-環(huán)戊二甲酸。用乙酰乙酸乙酯合成CH3COCH2CH2CH2COOHch3ch3BrCHgCOCHzBrCH3COCH2CH2CH2OH用乙酰乙酸乙酯合成用乙酰乙酸乙酯合成O. .1用丙二酸二乙酯合成1, 4環(huán)已二甲酸CH 369. CH3COCH3 ch3ch-c-ch

5、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, CHCH CH3CH2CH2CCH2CH2CH2CH376. 由丙二酸二乙酯合成環(huán)丁基甲酸。77. 由乙醇合成乙酰乙酸乙酯78. ©一OH80. 0 0081. 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ACOOH087.用丙二酸二乙酯合成環(huán)已基甲酸88.用乙酰乙酸乙酯合成2-甲基-4-戊酮酸89.OHd 一CHOOCHO90.no291.由 CH3CH2C

6、H2CH2Br CH 3CH 2CH-CHCH 3CH 3r 1CH3CH3NO 2由一 “CH2CH2CH393.ch2ch2ch399. CH2CH2 ch3r OH100.CH 2CH=CH 2101.aCH2CI-廠 ch2ch2ch2ci102.BrBr95.由1- 丁烯合成BrCH2CH2CH2CH2Br96.>Xx CH2CH2 CH3OH97.1 O CH 2 CH3_ OH98.XXCH2CH2CH2CHa：'"1 OHNO2103.OHBrBrOH*104.(CH 3)3CCH 2CHCH 3Br(CH3)3c：c二c：H(不多于四步)h'C

7、H3105. 由乙炔合成3,4-二羥基已烷。OH107.由甲苯合成106. 由環(huán)戊烷合成| CHCH3 其它試劑自選H3C O ch2ch3108.由苯合成IBr109. | 'SO3H1- COCH 3110.以銅鋰試劑合成1-苯基-2-甲基戊烷。111.以銅鋰試劑合成2-甲基已烷。112.以苯為原料合成苦味酸no2OHO2NNO 21 )NO2CH3OC2H5116.五個C原子以下的有機物合成_CH3d/C-CH3OH117. 以不多于4個C的有機物為原料合成：IJ Br118. 以丙烯為原料合成：CH 2-CH-CH 2Cl Cl Br119. 以丙烯為唯一有機原料合成：CH3I

8、ch3-c-ch 2ch 2chOH試題庫之五：合成題答案COOH114. 由正丁醇合成2-丁醇。a.CH3CI KMnO 4AICI 3CI23FeClBr?FeBr3NO2心心Clch3c.BrCI2FeCI3CH3ciFeCI3ClCl?COOHd.CH3CI2FeCI3KMnO 4Cle.Br2FeBr 3HNO 3NO2H2SO4BrCH3f.FB：3CH3CIKMnO4AICI 3COOHHNO3H2SONO2Br115. 由苯酚和兩個碳原子及以下的有機物合成2.OCH3BrHNO3Br2AlBr 3H2SO4FeBr3KMnO4COOHBrNO23.4.OH5.no2CH3CH

9、3g AH2SO4Br2hno3H2O BrBr100 cFeBr3h2so4180 C-*-TNO 26.8.CH3CH2CH2CH2OH ;款9.OHOH濃 H2S°4 、血100 e9.OH6 濃 H2SO4100 eOHSO3HSO3H10. CH2=CH2獸亠竺OH2SO4Br2OH- NaNH2CH 3CH 2cH 2°H we 丄乙醇.-hb：-HBr7.CH3CH2CH2OH NaMe2CHBr11. CH3CH2CH=CH 2 B2H6 聘2 CH3CH2CH2CH2OH12. CH3CH2OH _ Ag . HCN. H2O.550 e15.方法一:H2

10、SO4oh-HgSO4H2NiONaHBr MgH2O方法一：+液氨干醚H +16.17.18.CHNBS Mg尸十醚"CH2CIHCHOMgHCI Zn Cl 2干醚'CH2CIhchoHCI Zn Cl2CH3COCH 3 h2O _H +CH3CH2 C CH3OH19.CH3CH2CHOH3o+TMMgch3choh3o+干醚TMOCH3CH2BrMgAICI3*干醚HCHOH3O+ TM20. CHsCH=CHCH 3 :"OACH3CH-CHCH 3冷Oh OH21. CH3CH2CH2OH HBr 干醚 HCHO H眷 CH3CH2CH2CH2OH干醚

11、 h2O22. 方法一：CH3CHO+ CH3CH2MgBr H 產(chǎn) CH3CH2CHCH 322.方法二：CH3CH2CHO+ CH3MgBr 干醚 H CH3CH°CHCH 3OHO23.OBgMgFeCI3THF24.NBSMgTHFHCHOH2O25.26.I°2O2O. CH3CH2CH2OHB 干醚a廬0。 CO 2CH 3I.NaOEt CHaCOCH2BrBrCH 2(CH2)2CH2COOH CH3CH2CH2CH2OH3 稀 OH- CH2COCH 3 'H+ch2coch 327. CH3COOH Et°H Na0Et CH3COCH

12、 2COOEtNaOEt BrCH2CH2CH2Br NaOEt-HBr"HBryx COOEt J產(chǎn) COCH稀OH-328.CH3COOC2H5NaOEt CH3COCH2COOBtCH3*NaOEtBrCHCOOEtNaOEt BrCH 卜濃0H嚴 H：-HBrHOOCCH-CHCOOECH3CH329.HCN» _H2oH +30.31.NaCNMg干醚CH 20H2OH +KMnO 4Na 2CrO 7HCNH2OH+32.33.34.35.36.37.38.39.40.41.42.43.44.45.46.47.48.49.50.51.52.KMnO4P2。5方法

13、一:方法二：HBrNaCNH2OHBr MgCO2h2。干醚H+CH3BrKMnO4AICI 3Br2FeHgSO 4 KMnO 4EtOH + H2SO4HNa2CrO 7 Ba(OH) 2H2SO 4 LiAlH 4 HBr Mg環(huán)氧乙烷H2O KMnO 44干醚"»PBr3NaCN H2OEtOHA TAHHH2Och3coohHHNO3 Fe+HCI H2SO 4(CH3CO)2。HNO3H+乙酸NH3NiHBrMgCH3CHOh+ Na2CrO 7(CH3CO)2。 Fe Fe +HClBr2HNO2c6H5NH2<5 °C_HNO 3»

14、_Fe +HClHNO 2H2SO4<5COH»h2so濃 hno3- oh JCl2 Fe+HClFeCl3hno2 CuBr<5 C-HBr.(CH3CO)2。HNO 3H2O乙h+ *"(CH3CO)2Ohno3h2o乙酐 H 或OH -HNO3 NH4SHNaNO2 h2so4H2OH2SO4A 乙醇液05CHNO 3 Fe+HCl Br2 NaNO2H2SO4 H3PO2+H2OH2SO4 05CHNO3 Fe(CH3CO)2。H2SO4HClh2so4出。+Br2_ H2O LNaNO2 嚴180C HCl v 5CH3PO2h2oHNO3 Fe+H

15、ClB2 NaNO2 HCl出卩+匕。h2SO4 05C53.HNSH2SO4 Fe+HCICH3CO2O HNO 3H2O乙酸H，HNO 2 NaNO2HBF4<5Ccu粉54.HNO2CuBr -HBr<5 CHNO3Cl2Fe+HCIH2SO4 FeCl355. CH2COOC2H52NaOC2H5CH3BrNaOC2H5 CH2=CHCH2BrH + / H2OTM56. CH 3COCH 2COOEt EtONa CH3CH2CH2CH2BrEtONa CH3Br 酸式分解 TM57. CH3COOHP,Cl2NaCN EtOH 亍a -取代 NaOH H2SO4EtON

16、a CH2CH2Br2水解-2NaBr -CoTTM58. NaSHNaOH CH3CH23l HNO 3 AA-59.H2SO- PCl32N©CH3.60.Br2CH3COCIFe AlCl 3Zn / HgHClCH3CH2BrAICI361 2 EtONa 曠 2 EtONa 嚴 NaOH . BrCH2CH2Br CH2I2 HCl62. 2 EtONa Na OH _ 出0二 TM BrCH 24BrTM63.OH-A4 BrCH2CH2COOEt EtONa64.HNO3FeCH3CO2。Br2H3O+NaNO2 H3PO2H2SO4 HClHCl v 5 CH2O65

17、.HOCH 2CH2OHMg乙醚H3O +66. EtONa EtONa NaOHI l/l CH3CH2CH2BrCH3I ch3i EtONaNa OH67. BrCH 2CH2CHMe2酮式分解日噸3Cl2 Fe+HCI HN°2 . CuBr -HBr 2 EtONa 2EtONa504 FCNaOH<5 C687' BrCH2CH2Br BrCH 2CH2Br HCl69.70.71.Ni HCl MgCH3COCH3 H3O+H2 Zn CI2 干醚 2 EtONa BrCH23B：EtOCO2CHCH 23CHCOOEt NaOH2 HClTMEt0NaC

18、H3C0CITMH2O72 HN037e L H2SO4 L HN03 嚴 OHy'H2SO4 HCl保護氨基H2SO4 73.EtONa CH3COCH2CI *_OH TMH2O74.EtONa(CH3)2CHBr Na OH HCl"TM75. CH3CH=CH2 _* CH3CH2CH2BrCHCHNaNH2液氨ACH3CH2CH2BrNaNH2液氨76. 2EtONa CH2(CH2Br)2 水解 TM -2NaBr -CO2773沖讐 CH3ChH+2OHE囂 tm78._HNO3Fe (CH3CO)2O HNOH2SO4 HCl79.。3OH乙酐CHO80.81

19、._AZn /H2o羥醛縮合 -H2oCu HNO 3 BaO250 C脫羧脫水 EtONa EtONa Na OHHgO+.F C i Q C LJ D"TM C2H5Br C2h 5Br82. EtONa Na OH HCl&；BrOCOOHCH3CH2CH2MgH 3O83.CH3CH2CH2CHOJ84.» CH3CH2CH2CHCH2CH2CH3Cr°3B2OH乙酸EtONa CH3CH2CI EtONaC6H5CH2CI Na OHCH CH CHCOOHEtOHEtOHCH2C6H5干醚TM85. EtONa 2 EtONa Na OH TM

20、 BrCH 2COOEt CH3IOHO86.87. 2 EtONa Na OH Br(CH 2)5Br HCl CH3CH2MgBrEt2OCOOHAH3° +CH2CH3OH88.CH3EtONa C|-CHCOOC 2H 5 _ Na OHH3OtEtOHHOCH2CH2OHCrO3H3O+ tmCH3CCH2cHCOOHO2 - -CH389.保護醛基HN°3KMnO 4. Fe » 偽38)2。嚴 HNO3- H3o HClH2SO491. CH3CH2CH2Br HBr Na ,m90.H2SO4 NaNO2*HCl v 5C92. Ich3ch2co

21、ciaici3HNO3 H2SO4Zn-HgHClA TMOCH3CH2COCIBr2FeCl3Zn-HgHClCH2CH2CH394. gBrHNO3 - KMnO4 -AlCl3 eH+95. CH 2=CHCH 2CH3 NBS 乙醇H高溫 TM96. CH3CH2CH2MgX+ H2O / H+HSO4 B2H6CH2CH2 CH 3 H2O2/OH-OH97.98.或 CH3CH2CH2MgX H2O / H+HSO4 HBr / H2O2 NaOH /H2O CH3CH2MgXHSO4 B2H6CH2 CH3 H2° / HH2O2 / OH OH或 CH3CH2MgXHSO4 HBr / H2O2 H2O / H+ NaOH /H2O CH3(CH2)3MgXHSO4 B2H6CH2CH2cH2 CH3 h2° / H+ *H2O2/OH_ OH或 CH3(CH2)3MgXHSO4 HBr / H2O2 H2O / H+ NaOH /H2O100. 干醚;2O/H +3 CH2CH=CH 2或 NaC毛HNa/液氨101. 干醚OHSOCH2CH2CH2CIH2OSO2CICH