10 - 11章习题及参考答案-1

第十章 醇和酚

问题10.1写出下列化合物的构造异构体并命名.

(1) C5H12O (2) C4H8O 答案:

(1)CH3CH2CHCH2CH3CH3CH2CH2CHCH3CH3CH2CH2CH2CH2OH(CH3)3CH2OH3-戊醇OHHO2-戊醇OH正戊醇2,2-二甲基丙醇CH3CCH2CH3CH3CHCHCH3HOCH2CHCH2CH3CH3CHCH2CH2OHCH3CH2OCHCH3CHCH33CHCH33CHOH32-甲基-2-丁醇3-甲基-2-丁醇2-甲基-1-丁醇3-甲基-1-丁醇2-乙氧基丙烷CH3OCH2CH2CH2CH3CH3CH2OCH2CH2CH3CH3OCHCH2CH3CH3OCH2CHCH3CH3甲基丁基醚乙基丙基醚2-甲氧基丁烷2-甲基-3-甲氧基丙CH3烷(2)H3CCH2OHHCH2OHHCCCCHH(Z)-2-丁烯-1-醇H3C(E)-2-丁烯-1-醇CH2=C(CH3)CH2OHCH2=CHCHCH3OHCH2=CHCH2CH2OH2-甲基-2-丙稀-1-醇3-丁烯-2-醇3-丁烯-1-醇CH2OHCHOH3CH3OH环丁醇环丙基甲醇反-2-甲基环丙醇顺-2-甲基环丙醇OHH

问题10.2 上题中哪些化合物有立体异构体?写出它们的构型和名称.

答案:

(1)CH3CH2CH2CHCH3CH3CHCHCH3HOCH2CHCH2CH3CH3OCHCH2CH3OHCHOHCH33CH32R-戊醇3-甲基-2R-丁醇2R-甲基-1-丁醇2R-甲氧基丁烷

CH(2)3CHCH3OH2=CHCHCH3OHSSSR3-丁烯-2-醇反-2-甲基环丙醇顺-2-甲基环丙醇OH

问题10.3 (1) 将下列化合物命名:

(CH3)2CHCH2CH2CH2CH2OH(C6H5)3OH(CH3)2CHCH2CHCH2OHC6H5C(CH2CH=CH2)2CHOH3

(2)写出下列化合物的构造或构型.

3-甲基-2-戊醇 , 2-环己烯-1-醇 , (E)-4-庚烯-2-醇 , 叔戊醇

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答案: (1) 5-甲基己醇 三苯甲醇 2,4-二甲基戊醇 4-苯基-1,6-庚二烯-4-醇

HOHCH3OHCH3CH(OH)CH2CHCCH2CH3CH3CHCHCH2CH3（CH3）2C（OH）CH2CH3 问题10.4 下列化合物应如何合成?

(1)CHCHCHCH6523OH(2)C6H5C(CH3)2OH(3)CH3(4)CH3CH3CH2CCH2CH3OHCH3CHCH3(CH2)4C(CH2)4CH3OHCH3(5)(6)CH3CH2CHCH2CH(CH3)2OH(7)(C6H5)3CCH2OH(8)CH3CH2CCOHC6H5CCH2CH3OH

答案:

(1)CH3CH2BrMg乙醚CHOCH3CH2MgBrCHOMgBrCH2CH3OMgBrH3OC6H5CHCH2CH3OH

(2)OCCH3CH3MgBrC(CH3)2H3OC6H5C(CH3)2OH或从苯和丙酮合成更好

CH3(3)OMgBrOCH3MgBrCH3CH2CCH2CH3CH3CH2CCH2CH3CH3H3OCH3CH2CCH2CH3OH从乙醇和2-丁酮更好

CH3CH3(4)CH3CO(CH2)4CH3CH3(CH2)4MgBrCH3(CH2)4C(CH2)4CH3OMgBrH3OCH3(CH2)4C(CH2)4CH3OH从乙酸乙酯和1-戊醇

(5)OCH3CH2CH(CH3)2CHCH2MgBrCH3CH2CHCH2CH(CH3)2OMgBrH3OCH3CH2CHCH2CH(CH3)2OH从丙醇和异丁烯

(6)(C6H5)3CBrOHCHO(C6H5)3CCH2OMgBrCH3CNaH3O(C6H5)3CCH2OH三苯基溴甲烷的合成？

CH3(7)CH3CH2CCH3HCCH3CH2CCONaCHH3OCH3CH2CCOHCH

(8)OCCH3OMgBrCH3CH3CH2MgBrCCH3CH2CH3H3OC6H5CCH2CH3OH

问题10.5如何由下列原料合成1-苯乙醇(C6H5CH(OH)CH3?

2

(1)溴苯 (2)苯甲醛 (3)苯乙酮 (4) 苯乙烯 答案:

(1)BrMgMgBrCH3CHOCH3(2)乙醚CHOCH3MgClOHCH3H3O(3)OHOCH3NaBH4H2OH+OHCH3(4)CHCH2OHCH3

问题10.6如何由下列原料合成2--苯乙醇(C6H5CH2CH2OH)? (1)溴苯 (2)苯乙烯 (3)苯乙炔 (4)苯乙酸乙酯 答案:

(1)Br1. Mg, Et2OOMgBrH2O,H+OH(2)CH=CH21. B2H62. H2O2,OHOH2.(3)CCHOCH=CH21. B2H62. H2O2,OHOH(4)OCH2COEtlindlerLiAlH4CH2CH2OH

问题10.7 1,2--,1,3—和1,4—环己二醇各有几种立体异构体. 答案:1，2-，1，3-各有三种，1，4-有两种如下图所示

OHOHOHOHOHOHOHOH,OHOH,OH_+_+OH

问题10.8 写出下列化合物用高碘酸氧化生成的产物.

CH3OHOHCH3CH3OHCH2OHOHOHOHOH

O答案:

OCH3O,OOO,HCHO,O

问题10.9 氯苯酚和环己醇如何分离?

答案: 在混和液中加入氢氧化钠溶液,对氯苯酚在无机层中,加乙醚萃取环己醇，分出有机层，蒸

去乙醚再进行常压蒸馏即得到环己醇, 水相酸化可得到对氯酚.

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问题10.10 写出下列反应的产物.

OH(1)H3COH(2)CH3H(CH3)2CCH2C2CH3Br2, CHCl3H0℃2SO4(3)OHBrCHOCH3CH2CCl,AlCl3O(4)HNO3,HOAcOCH3CH3OH

答案:

(1)H3COHOH(2)HCH3C2CH3OHBr(3)CCH2CH3(4)CHOBrOCHO2NOCH33OH

习题

1. 推测下列反应的机理。

CH6H5C6H5H(1)H+(2)OHOHBrHH3C3COH

CH2=CH2CH3

(3)OOHH+OH100%(4)H+++

答案：

CH6H5CH6H5C6H5+H(1)H+-H2OOHOHH3C2+ 4