试题库五——合成题及解答

1．由苯或甲苯及其它无机试剂制备：

COOHNO2CH3COOHNO2COOHCH3 BrBr a.b.c.Cld.e.f.g.BrBrNO ClCOOHClClBr2NO2

Br2．

NO2

CH3COOH3． CMe

COOH3 4．

NO2 5． OHO

6． CH3CH2CH2OH → CH3C≡CH 7．CH3CH2CH2OH → CH3CH2CH2OCH(CH3)2

8．CH3CH2CH2CH2OH → CH3CH2CH(OH)CH3 9． OHOH

SO3H10．CH2=CH2→ HOCH2CH2OCH2CH2OCH2CH2OH 11．CH3CH2CH=CH2 → CH3CH2CH2CH2OH 12．CH3CH2OH → CH3CH(OH)COOH 13． COClCO14．

OOH

15．HC≡CH → CH3CH2CH2CH2OH 16． CHCH33CH

2CCH3OH

1

17． 18． CH2CHCH3OH 19． CH2CH2CH2OH

20．CH3CH=CHCH3 → CH3CH-CHCHOOHOH21．CH3CH2CH2OH → CH3CH2CH2CH2OH

22．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． BrCH2(CH2)2CH2COOHOO 26． OCO2CHO3CH2COCH3

27． CH3COOHCOCH328． CH3COOC2H5HOOCCH-CHCOOEt

CH3CH3 29. COOHO

OH 30． CH3CH2CH2BrCH3CH2CH2COOH

31． (CH3)2CHOH(CH3)2CCOOH OOH32． CH3O O CHO3OO33．(CH3)2C=CH2 →(CH3)3CCOOH

COOH34．

Br

2

35． HC≡CH → CH3COOC2H5 36． O O

37．CH3CH2COOH → CH3CH2CH2CH2COOH 38．CH3COOH → CH2(COOC2H5)2 CO39． 2CH3COOH OHOOCCH340． NH2

NH2NH241．

NO242． CH3CH2OHCH3CHCH2CH3 N H 2

43． NH 2 NHCOCH 3

NO244． N N

45． CH3NNCH3OH 46． NH 2 NH 2 NONHNH2247． 2

NO48． NH2 2 NH 2

NO2OH49． BrNO

Br250．

Br 3

51． BrBrBr 52． CH3CH3

BrBrNO253．

NO254． Cl

Br55．由CH2(COOC2H5)2合成 H3CCHCOOH

CH2CH=CH256．由CH3COCH2COOC2H5合成 CH3CH2CH2CH2CH-CH3

COOH57． CH3COOHCOOH58．CH 3(CH2)3OHCH3(CH2)3SO2(CH2)3CH3 CH 3 59． H 3 C SO 2 NH CH 3 60． CH3CH2Br

61．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。 CH64．

3CH3

Br65． CH

3COCH2BrCH3COCHO2CH2CH2OH66． 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。

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69． CH3CH

3COCH3CH3CH-C-CH3CH70．由丙二酸二乙酯合成庚二酸3OH

71．由乙酰乙酸乙酯合成2,4－戊二酮 72.

NH2

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≡CHCH3CH2CH2CCH2CH2CH2CH376. 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. NH2NO2 79. CHO OH80.

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 OCOOH O83.

CHOBr84.由丙二酸合成2-苄基丁酸。

O85.由乙酰乙酸乙酯合成 OEt OOHCH2CH386.

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.

OHOCHOCHO

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90.

CH3CH3NO2OH91. 由CH3CH2CH2CH2BrCH3CH2CH-CHCH3CH3 CH3CH3NO292. 由CH 2CH2CH393. CH2CH2CH3

BrCOOH94．

NO295. 由1-丁烯合成BrCH2CH2CH2CH2Br96. OCH2CH2 CH3OH OCH2 CH397. OH

OCH2CH2CH2CH398. OH 99. OCH2CH2 CH3OH 100. CH2ClCH2CH=CH2 101． CH2ClCH2CH2CH2Cl Br102. Br NO2 OH103. BrBr

OH104. (CH(CH3)3CH3)3CCH2CHCH3BrHCCCH3

(不多于四步)6

105. 由乙炔合成3,4-二羟基已烷。

106.由环戊烷合成 OHCHCH 3 （其它试剂自选）

107.由甲苯合成 H3CCH2CH3

108.由苯合成 Br SO3H109.

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。

OH112. 以苯为原料合成苦味酸( ) O2NNO2OH113. NO2NO2

NO2114.由正丁醇合成2-丁醇。

115.由苯酚和两个碳原子及以下的有机物合成 CH3OC2H5

CH3116.五个C原子以下的有机物合成 C-CH3

OH117.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 2-CH-CH2ClClBr119. 以丙烯为唯一有机原料合成： CH3CH3-C-CH2CH2CH3 OH

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试题库之五：合成题答案

1． COOH CH3ClCl2 a.KMnO4AlCl3FeCl3Cl

NO2CH3CH3 b.HNO3Br2c.Cl2Cl2Cl H2SO4FeBr3BrFeCl3FeCl3Cl

COOHNO CH32KMnO4 d.Cl2FeCle.Br2HNO33FeBr3H2SO4

ClBr

CH3CH3 g.H2SO4Br2HNO3H2OBrBr100℃ FeBr3H2SO4180℃ NO2CHCOOH 3KMnO4HNO3 f.Br2CH3ClFeBr3AlCl3H2SO4 NOBr2

COOH2. CH3BrHNO3Br2KMnO4Br AlBr3H2SO4FeBr3

NO23． CH3COOH (CH3)3CBrKMnOAlCl4 3CMe3

COOH 4.CH3BrHNO3KMnO4

AlBr3H2SO4

OHONO2 5.K2CrO7

6.CHCHCBr2OH-NaNH2 32H2OHH2SO4170℃乙醇-HBrHBr 7.CH3CH2CH2OHNaMeBr-2CH

8.CH3CH2CH2CH2OHH2SO4H+ 170℃H2OOHOH OHOH浓 9.浓H9.H2SO42SO4100℃100℃ SO3HSO 3HOCHOAgO 10.22=CH2/H2O250℃ 8

11.CH3CH2CH=CHB22H6H2O-2 OHCH3CH2CH2CH2OH12. CHAgHCNH2O3CH2OH550℃ COCl13.CCO6H6

AlCl3

14. ONaBH4OH15. H2SO4 方法一：OH-H2HgSO4△Ni15.

O 方法二：NaHBrMgH2O液氨干醚H+ CH

3CH3NBSMgCH3COCH3H2OCH2CCH3 干醚H+CH2OH17. ClHCHOMgCH3CH2CHOH3O+

HCl，Zn Cl2干醚TM18. CHHCHO2ClMgCH 3CHOH3O+HCl，Zn Cl2干醚TM

19.CH3CH2BrMgHCHOH3O+

AlCl3干醚TM 20.CH3CH=CHCH3KMnO4-H2OCH 冷OHH+3CH-CHCH3OHOH 21.CHMgH3CH2CH2OHHBrHCHO2O

干醚H+CH3CH2CH2CH2OH 22.方法一：CHH3CHO+CH3CH2MgBr干醚2OH+CH3CH2CHCH 3H

22.方法二：CH3CH2CHO+CH3MgBr干醚2OOHH+CH3CH2CHCH3

OOH 23.Br2MgH2OCH2CH2OH FeCl3THFH+

24. CH3NBSMgHCHOH2OCHTHFH+2CH2OH

25.BrCH-OO2(CH2)2CH2COOHOH

H2O△ OCOO2CH3CO2CH3-H+OCH2COCH3 26.NaOEtCH3COCH2Br稀OHCH2COCH3△

27.CH3COOHEtOHNaOEtCH3COCH2COOEt NaOEtBrCHCOOEt2CH2CH2BrNaOEt

-HBr-HBrCOCH稀OH-COCH33

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16. 28.CH3COOC2H5NaOEtCH3COCH2COOEtCH3 -+ NaOEtBrCHCOOEtHHOOCCH-CHCOOEt

-NaOEtBrCH3浓OHHBrCH3CH3 H2O

29.HCNH+ ①NaCNH2O30．

H+H2OKMnO4 ②Mg干醚CH2OH+ 31.Na2CrO7HCNH2O

H+32．

KMnO4P2O5 △ 33.方法一：HBrNaCNH2OH+ 方法二：HBrMgCO2H2O

干醚H+ 34.CH3BrKMnO4Br2

AlCl3Fe 35.HgSO4KMnO4EtOH

H2SO4H+36．

Na2CrO7Ba(OH)2 H2SO4△△37. LiAlH4HBrMg环氧乙烷H2OKMnO4 干醚H+ PBr3NaCNH2OEtOH 38.H+H+ H2O 39.H+CH3COOH HNO3Fe+HCl 40.H2SO4

41．

(CH3CO)2OHNO3H+

乙酸42． HBrMgCH3CHOH+Na干醚2CrO7NH3 Ni43． (CH3CO)2O

44．

FeFe+HClHNO2C6H5NH2 Br2<5℃ OH 45.HNO3Fe+HClHNO

H22SO4<5℃HNO3ClFe+HClHNO46．

H2SO4浓HNO3OH -H2SOFeCl22CuBr-HBr4△3<5℃

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47.(CH3CO)2OHNO3H2O

乙酸H+48．

(CH3CO)2OHNO3+H2O 乙酐H或OH -49． HNO3NHSHNaNO2H2SO4HH乙醇液42SO4△0~5℃2O

△50．HNO

3Fe+HClBrSOH2NaNO2H24H3PO2+H2O2SO4△0~5℃ HNO 51.3Fe(CH3CO)2OHH2SO4H3O+Br2H2ONaNOH32SO4HCl△2PO2

180℃HCl＜5℃H2O 52.HNO3Fe+HClBr2NaNO2HClH3PO2+H2OH2SO4

△0~5℃ 53.HNO3Fe+HClHSO(CH3CO)2OHNO3H2OHNO2NaNO242HBF4

△乙酸H+<5℃Cu粉54． HNO3ClFe+HClHNO HCuBr-HBr2SO4△FeCl223<5℃+55. NaOC2H5CH3BrNaOC2H5CH2=CHCH2Br H / H2O

CH2(COOC2H5)2△TM56. CH3COCH2COOEtEtONaCH3CH2CH2CH2BrEtONaCH3Br酸式分解 TM57.

CHP,ClNaCN3COOHα-取代2EtOHEtONaCH2(CH2Br)2水解NaOHH2SO4-2NaBr

△-CO2TM58．NaSH NaOHCH3(CH2)3IHNO3

59．

H2SO4PCl3H2NCH3 60.Br2CHZn / HgFeAlCl3COCl3HCl 或CHAlCl3CH2BrBr3Fe2 61.①2EtONa①2EtONa①NaOH②BrCH2CH2Br②CH2I2②HCl△ 62.①2EtONaNa OHH3O+ ②Br(CH2)4BrTM 63.①EtONaOH- ②BrCH2CH2COOEt 64.HNO3Fe(CH3CO)2OBr2HNaNO HHCl3O+2H3PO22SO4△HCl＜5℃H2O 65.HOCH2CH2OHMgOH3O+乙醚 66.①EtONa①EtONaNaOH②CH3CH2CH2Br②CH3ITM

67.Na OH②BrCH①EtONa2CH2CHMe2酮式分解HNOTM3Cl2Fe+HClHNOHFeCl2CuBr-HBr2SO4△3<5℃

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68.①2EtONa①2EtONa①NaOH

②BrCH2CH2Br②BrCH2CH2Br②HCl△ 69.NiHClMgCH3COCH3H3O+H2Zn Cl2干醚 70.①2EtONa(EtOCO) ②Br(CH2)2CH(CH2)3CH(COOEt)2①NaOH②HClTM71.EtONa3BrCH3COClOH-△ H2OTM 72.HNO3FeHHNO3

H2SO4OH-2SO4△HCl保护氨基H2SO4△ 73.EtONaCH3COCH2ClOH-TM

H2O74.EtONa(CH3)2CHBr ①Na OH②HCl△TM

75.CH3CH=CH2HBrCH3CH2CH2Br CH≡CHNaNH2CH3CH2CH2BrNaNH2CH3CH2CH2Br 液氨液氨TM CH 76.2EtONa2(CH2Br)2水解-2NaBr △-CO2TM 77.CHKMnO3CH2OH4CH3CH2OHEtONaH+H+TM 酯缩合HNO 78.3HFe(CH3CO)2OHNO3H2O2SO4△HCl乙酐H+或OH -

79.①O3OH- ②Zn/H2O羟醛缩合-△H2OCHO 80.CuHNO3BaO250℃

脱羧△脱水 81.①EtONaH①EtONa②CNa OHHBr3O+25Br②C2H5△△TM O 82.①EtONaNa OHHCl△COOH

②O

Br 83.CHCH3CH2CH2CHO3CH2CH2MgH3O+CH3CH2CH2CHCH2CH2CH3CrO3Br2TM干醚乙酸 OHC 84.EtONaEtOHCH3CH2ClEtONa6H5CH2Cl①Na OHEtOH②HCl△CH3CH2CHCOOH CH2C6H5 85.①EtONaCOOEt①2EtONaNa OH②BrCH②CH3ITM2 OHO 86.NiCrO3CHCH2CH3

H3CH2MgBrH3O+2EtOOH2

87.①2EtONa①Na OHCOOH②Br(CH2)5Br②HCl△

CH388.EtONaCl-CHCOOC2H5Na OHH3O+EtOH△△CH3CCH2CHCOOH

OCH312

HOCH2CH2OHCrO3H3O+ 89.保护醛基TM 90.HNO3KMnO4Fe(CH3CO)2OHH2O HHNO33O+NaNO22SO4△NaOHHClH2SO4HCl＜5℃ 91.CH3CH2CH2BrHBrNa乙醇TM

92.CH3CH2COClHNO3HZn-HgAlCl△2SO4HClTM

3 93.CH3CH2COClBr2Zn-HgCH2CH2CH3

AlCl3FeCl3HCl94． CH3BrHNO3KMnOBr

AlCl43H2SO4△H+ 95. CH2=CHCH2CH3NBSNaOHBr2乙醇高温TM 96. ①CH3CH2CH2MgXHSO4①BCH2CH2 CH3②H2O/H+2H6△②H 2O2/OH-OH或①CH3CH2CH2MgXHSO4①HBr/H2O2 ②H2O/H+△②NaOH/H2O CH2 CH3 97.①CH3CH2MgXHSO4①B2H6②H2O/H+△②HOH 2O2/OH-CH

或①3CH2MgXHSO②H2O/H+4①HBr/H2O2△②NaOH/H2O CH 98.①CH3(CH2)3MgXHSO4B2H62CH2CH2 CH3

②H2O/H+①△②H2O2/OH-OH 或①CH3(CH2)3MgXHSO4①HBr/H②H+2O2②NaOH/

2O/H△H2O 99.①CH3CH2CH2MgXHSO4①BCH2CH2 CH3+2H6②

②H2O/H△H2O2/OH-OH 或①CH3CH2CH2MgXHSO4+①HBr/H2O2 ②H2O/H△②NaOH/H2O CH3BrHNO3KMnO AlCl43H2SO4△H+

101.Mg①OH2OSO2ClCH2CH2CH2Cl干醚 ②H2O/H+OH-102.Br 2HNO3Br2FeHFe 2SO4OH 103.H2SO4NBSH2OBr2170℃NaOH

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(CH)CH 104.(CH333)3CCH2CHCH3KOHBr

Br△2KOH△NaCC液氨HCH3 105. CH≡CHNaNH2EtBrNaNH2EtBrPd/CKMnOH4CH2OH-冷3CH2CHCHCH2CH3 OHOH 106.Cl2MgCH3CHOH3O+光干醚TM

CH3CH3 107.ZnCl2甲苯HCl，HCHOAlCl3TM CH2Cl 108.H2SO4Br2 FeBrTM3 光HgSO109.

ClCH≡CNa42H2OTM

110.

(CH3CH2CH2CH)2-CuLi+CH2BrCH2CHCH2CH2CH3 CH111.(CH3CH33CH)2-CuLi+CH3CH2CH2CH2BrCH3CHCH2CH2CH2CH3 CH3CH3 112.Br2HNO3OH-

FeHNOH32SO4△H2OH2SO4TM 113.ClHNOHNO

Fe233OH-H2SO4△HTM2SO4△H2O114. CHH3CH2CH2CH2OH2SO4HBrOH- 170℃HTM2O 115.OHCH3BrNa OHCH3CH2Br AlClTM3

116. +HBrMgCH3COCH3H △Br3O+干醚TM117.

+△BrTM118. CH2=CHCH3Br2CH2=CHCH2BrCl2 高温室温CH2-CH-CH2ClClBr HBrMg119. CH2=CHCH3HOCH3CH22干醚2CH2BrH3O+ CH2=CHCH3HBrOH-NaTM2Cr2O7CH3COCH3

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