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：

COOH NO2COOHCH3 Cld.e.c.a.b.

BrCl ClCOOHCl Br2． NO2 COOHCH3

3．

CMe3 COOH 4． NO2 OHO5．

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

NO2COOHCH3BrBrNO2Brf.Brg.NO28．CH3CH2CH2CH2OH → CH3CH2CH(OH)CH3 9．

SO3HOHOH10．CH2=CH2→ HOCH2CH2OCH2CH2OCH2CH2OH 11．CH3CH2CH=CH2 → CH3CH2CH2CH2OH 12．CH3CH2OH → CH3CH(OH)COOH 13． 14．

COClCOOOH

15．HC≡CH → CH3CH2CH2CH2OH 16． 17． 18． 19．

CH2CH2CH2OHCH3CH3CH2CCH3OHCH2CHCH3OH20．CH3CH=CHCH3 → CHCH-CHCHO321．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． 26．

27． CH3COOHCOCH3OHOHBrCH2(CH2)2CH2COOHOOOCO2CH3OCH2COCH328． CH3COOC2H5HOOCCH-CHCOOEtCH3CH3

COOH29. OOH

CH3CH2CH2COOH 30． CH3CH2CH2Br

(CH3)2CCOOH31． (CH3)2CHOH OHOO32． CH3O OCH3 OO33．(CH3)2C=CH2 →(CH3)3CCOOH

COOH34．

35． HC≡CH →

OBrCH3COOC2H5

36． O

37．CH3CH2COOH → CH3CH2CH2CH2COOH 38．CH3COOH → CH2(COOC2H5)2 39． 40．

NH2NH2CO2CH3OHCOOHOOCCH3NH241．

NO242．

NH

2CH3CH2OHCH3CHCH2CH343． NHCOCH 3

NO2NH244． N N

45． OH NH2NH246．

NO2 NH2NH247．

NO2

NH248． NH

2CH3NNCH3

NO2OHBr49．

NO2Br50． 51． 52． 53．

NO2ClBrBrBrBrCH3CH3BrNO2Br54．

Br55．由CH2(COOC2H5)2合成

H3CCHCOOHCH2CH=CH256．由CH3COCH2COOC2H5合成 CH3CH2CH2CH2CH-CH3

57． CH3COOH58． 3(CH2)3OHCHCOOHCOOHCH3(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。 64． Br65． CH3COCH2BrCH3COCH2CH2CH2OHO

66． 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。 CH369． CH3COCH3CH3CH-C-CH3 CH3OH70．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

OCH3CH375. CHCH=CH，32CH≡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. 79. 80.

OHONH2NO2CHO81.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 83.

CHOBrOCOOHO84.由丙二酸合成2-苄基丁酸。

85.由乙酰乙酸乙酯合成 86.

OHOOEtCH2CH3OHO87. 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. CH390.

CHOOHNO2OHOCH3CHO91. 由CH3CH2CH2CH2Br 92. 93.

BrCOOHCH3CH2CH-CHCH3CH3CH3CH3NO2由CH2CH2CH3CH2CH2CH394．

NO295. 由1-丁烯合成BrCH2CH2CH2CH2Br96. 97.

OOCH2CH2 CH3OHOCH2 CH3OHCH2CH2CH2CH3OH98. 99. 100. 101． 102.

OHCH2ClOCH2CH2 CH3OHCH2ClCH2CH=CH2CH2CH2CH2ClBrBrNO2BrBr103.

104. (CH3)3CCH2CHCH3Br(CH3)3CHOHCCHCH3(不多于四步)105. 由乙炔合成3,4-二羟基已烷。

106.由环戊烷合成 CHCH 3 （其它试剂自选）

107.由甲苯合成 H3CCH2CH3

Br108.由苯合成 SO3H109. COCH3

110.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。

OHNO2O2N112. 以苯为原料合成苦味酸( ) 113.

OHNO2NO2NO2114.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

116.五个C原子以下的有机物合成

117.以不多于4个C的有机物为原料合成： CH118.以丙烯为原料合成： 2-CH-CH2ClClBrCH3OC2H5CH3C-CH3OHBr119. 以丙烯为唯一有机原料合成： CH3-C-CH2CH2CH3OH

CH3试题库之五：合成题答案

1．

COOH CH3ClKMnO4Cl2a. AlCl3FeCl3Cl

NO2CH3

Cl2Br2HNO3Cl2 b.c.FeCl3FeCl3H2SO4FeBr3 Br COOHCH3 Br2HNO3KMnO4Cl2e. d.CH3HFeBrC33H2SO4FeCl3Br BrHNO3Br2H2OH2SO4g.Cl 100℃180℃FeBr3H2SO4 COOHCH3NO2

Br2KMnO4HNO3CH3Cl f.FeBr3AlCl3H2SO4 NO2COOHBr

Br HNOCH3BrBr23KMnO42.H2SO4AlBr FeBr33

NO2COOHCH33．

(CH3)3CBrKMnO4 AlCl3

CMe3COOH

HNOCH3BrKMnO434.HSO AlBr243 OHONO2

K2CrO7 5.Br2NaNH2 6.CHCHCHOHH2SO4OH-322-HBr170℃乙醇

HBrMe2CHBr- CHCHCHOHNa7.322

H+ 8.CHCHCHCHOHH2SO43222H2O170℃ OHOHOHOH

浓H2SO49.浓H2SO4 9.100℃100℃

SO3HOO SO3HAgH2O 10.CH2=CH2O2/250℃

H2O2 11.CHCHCH=CHB2H6CH3CH2CH2CH2OH322OH- AgH2OHCN12.CH3CH2OH

550℃

COClCO CH66 13.AlCl3 NaBH4OHO14.

H2SO4H2OH-15.方法一： HgSO4Ni△O

Na H2OHBrMg15.方法二：干醚CH3 液氨H+CH3 NBSCH3COCH3H2OMg16.CH2CCH3+ H干醚CHCl2OH MgHCHOH3O+CH3CH2CHO17. TM干醚HCl，Zn Cl2 CH2ClMgCH3CHOH3O+HCHO 18.TM+干醚HCl，Zn ClMg HOCH2CHBrHCHO332TMAlCl3 19.干醚H2O 20.CHCH=CHCHKMnO4CH3CH-CHCH33-3H+ 冷OHOHOHCH3ClClNO2Br H2OMgCH3CH2CH2CH2OH21.CH3CH2CH2OHHBr干醚HCHO H+H2O 22.方法一：CH3CHO+CH3CH2MgBr干醚H+CH3CH2CHCH3

OHH2OCH3CH2CHO+CH3MgBr干醚 22.方法二：+CHCH32CHCH3H OOH Br2MgH2OCH2CH2OH+THF 23.FeClH3

H2OHCHOMgCH2CH2OHCH3NBS +24.HTHF

OO OH- 25.BrCH2(CH2)2CH2COOHH2O△OO O+COCHCH2COCH3COCH23-H23 稀OHCH3COCH2BrNaOEtCH2COCH3△ 26. 27.CH3COOHEtOHNaOEtCH3COCH2COOEt COOEt稀OH-COCH3 NaOEtBrCH2CH2CH2BrNaOEtCOCH--HBr3HBr

28.CH3COOC2H5NaOEtCHCOCHCOOEt32 CH3- BrCH3H+HOOCCH-CHCOOEt浓OHNaOEtBrCHCOOEtNaOEt -HBrCH3CH3H2O HCNH+ 29.NaCNH2O

①H+30． KMnO4H2OMg②+ CH2OH干醚H2O 31.Na2CrO7HCNH+

△

H2O 33.方法一：HBrNaCNH+

MgH2OCO2 方法二：HBrH+ CH3BrKMnO4干醚Br2 34.AlCl3FeHgSO4 EtOHKMnO435. H2SO4H+36． Na2CrO7Ba(OH)2H2SO4△△

Mg H2OKMnO4环氧乙烷LiAlH4HBr37. 干醚H+ PBr3EtOHNaCNH2O38. H+H+H2O CH3COOH39.+ HHNO3 Fe+HCl40. H2SO4

(CH3CO)2OHNOH+341．

乙酸

H+Na2CrO7NH342． HBrMgCH3CHO干醚Ni

43． (CH3CO)2O

C6H5NH2HNO2Fe+HCl44． Fe<5℃Br2

OH

HNO3 HNO2Fe+HCl 45.HNO3H2SO4<5℃Cl2Fe+HClHNO2-46． H2SO4浓HNO3OH H2SO4△FeCl3<5℃

32．

KMnO4P2O5CuBr-HBrH2O 47.(CH3CO)2OHNO3乙酸H+

H2O48． (CH3CO)2OHNO3+乙酐H或OH -

HNO3NH4SHNaNO2H2SO4H2O49．

H2SO4△乙醇液0~5℃△

HNOFe+HClBr2NaNO2H2SO4H3PO2+H2O50． H2SO430~5℃△

(CH3CO)2OBr2FeH2SO4H3O+H2OH3PO2NaNO2 51.HNO3H2SO4HCl△H2O 180℃HCl＜5℃HPO+HOHNOFe+HClBr2NaNO2HCl3223 52.H2SO4△0~5℃

HNOFe+HCl(CH3CO)2OHNO3H2O3HNO2 53.NaNO2HBF4HSO+24△ 乙酸H<5℃Cu粉Fe+HClHNO254． HNO3Cl2CuBr-HBrH2SO4△FeCl3<5℃

H + / H2ONaOC2H5CH2=CHCH2BrCH3BrNaOC2H555.TM CH2(COOC2H5)2△CH3CH2CH2CH2Br EtONaEtONaCHBr3酸式分解56.CH3COCH2COOEtTM

NaCNCH2(CH2Br)2EtONa水解EtOH CH3COOHP,Cl257.TMα-取代HSONaOH-CO-2NaBr242△

CH3(CH2)3IHNO3NaOH58．NaSH

CH359． H2SO4PCl3H2N

Zn / HgCH3COCl 60.Br2FeAlCl3HCl CH3CH2BrBr2或 AlCl3Fe①EtONa①①NaOH2EtONa2 61.②HCl△②BrCH2CH2Br②CH2I2

H3O+ 62.①2EtONaNa OHTM②Br(CH2)4Br

OH- 63.①EtONa②BrCH2CH2COOEt

HNO3 (CH3CO)2OBr2FeH3O+H3PO2NaNO264. HClH2SO4△HCl＜5℃H2O

MgH3O+O 65.HOCH2CH2OH乙醚

NaOH①EtONa①EtONa 66.TM②CH3I②CH3CH2CH2Br

Na OH①EtONaTM 67.②BrCH酮式分解2CH2CHMe2 68.①2EtONa①2EtONa①NaOH ②HCl②BrCH2CH2Br②BrCH2CH2Br△

MgHClCH3COCH3H3O+ 69.NiZn Cl2干醚H2 70.①①NaOH2EtONa(EtOCO)2CH(CH2)3CH(COOEt)2TM②HCl ②Br(CH2)3Br△Cl2Fe+HClHNO2EtONaOH-HNO3CH3COClCuBr-HBr 71.TMHSO24FeClH2O△3<5℃HNO3 72.HNO3FeH2SO4OH- H2SO4△HCl保护氨基-H2SO4△CH3COCH2ClOH 73.EtONaTMH2O (CH3)2CHBrEtONa①Na OH 74.TM△②HCl

75.CH3CH=CH2HBrCH3CH2CH2Br

NaNH2CH3CH2CH2BrNaNH2CH3CH2CH2Br CH≡CHTM液氨液氨

CH2(CH2Br)2水解 76.2EtONaTM-CO-2NaBr2△

KMnO4CH3CH2OHEtONa77.CH3CH2OHTM+HH+酯缩合

HNO3Fe(CH3CO)2OH2OHNO3 78.+HSO乙酐△HCl24H或OH -

①O3OH-△79.CHO ②Zn/H2O羟醛缩合-H2OHNO3BaO 80.Cu△250℃ 脱羧脱水EtONaH3O+Na OH①EtONa 81.①CHBrTM②25②C2H5Br△△ O HCl①EtONaNa OH△COOHO 82.②

CH3CH2CH2MgH3O+Br2Br 83.CH3CH2CHCH3CH2CH2CHCH2CH2CH3CrO3TMCHO2乙酸干醚OH

C6H5CH2ClEtONaCH3CH2Cl①Na OHEtONa 84.EtOHCH3CH2CHCOOH②HClEtOH△CH2C6H5

Na OHEtONaEtONa①2 85.①TMCH3I②BrCH2COOEt②

OHO CH2CH3CrO3NiCH3CH2MgBrH3O+86. OHH2EtO2COOH ①2EtONa①Na OH 87.②Br(CH2)5Br②HCl△CH 3 88.EtONaH3O+Cl-CHCOOC2H5Na OHCH3CCH2CHCOOH EtOH△△+CrO3CH3H3OO 89.HOCH2CH2OHTMHNO3 90.保护醛基KMnO4(CH3CO)2OH2OFeH3O+NaNO2HNO3 H2SO4△HClH2SO4HCl＜5℃NaOHHBrNa 91.CH3CH2CH2BrTM乙醇

Zn-HgCH3CH2COClHNO3H2SO4 92.TM△HClAlCl3

Zn-HgCH3CH2COClBr2CH2CH2CH3

93. AlCl3FeCl3HClHNO3KMnO494． CH3BrBrAlCl3+HSO△24H

Br2 CH2=CHCH2CH3NBSNaOHTM95.乙醇高温 CH2CH2 CH3HSO4①CH3CH2CH2MgX①B2H6 96.+②H2O2/OH-②H2O/H△OH

CHCHCHMgXHSO4 ①HBr/H2O2或①32+2 ②NaOH/H2O②H2O/H△CH2 CH3CH3CH2MgXHSO4B2H6①① 97.+②H2O/HOH②H2O2/OH-△

CHCHMgXHSO4①HBr/H2O2 或①32+②NaOH/H2O②H2O/H △CH2CH2CH2 CH3HSO4①CH3(CH2)3MgX 98.①B2H6+②H2O/HOH ②H2O2/OH-△ HSO4①HBr/H2O2或①CH3(CH2)3MgX +②NaOH/H2O②H2O/H△

CH2CH2 CH3 HSO4①CH3CH2CH2MgX①B2H699.+ ②H2O2/OH-②H2O/H△OH

HSO4①HBr/H2O2或①CH3CH2CH2MgX +②NaOH/H2O②H2O/H△

CH2CH2CH2ClH2O①OSO2Cl 101.Mg干醚OH- ②H2O/H+Br2Br2HNO3 102.FeFeH2SO4 HNO3CH3BrKMnOOH103.H2SO4170℃NBSH2ONaOHBr2AlCl34H2SO4△H+

(CH3)3C 104.(CH)CCHCHCHKOHBr2KOHNaC3323H△△液氨 Br

Pd/CNaNH2NaNH2EtBrEtBrKMnO4CH≡CH 105.H2OH-冷

H3O+MgCH3CHOCl2TM 106.干醚光

CH3CH3

107.ZnCl2HCl，HCHO甲苯AlCl3CHCH3CH3CH2CHCHCH2CH3OHOHTMCH2Cl