徐寿昌主编《有机化学》(第二版)-课后1-13章习题答案

有机化学课后习题答案

CH3C6H5C=CCH3HB2H6NaOH,H2O2CH3C6H5CHCHOHCH3CH3B2H6CH2=CCH2CH2CH36. 写出下列化合物的脱水产物。

解: (1) (3) CH3CH=C(CH3)2 NaOH,H2O2CH3HOCH2CHCH2CH2CH3

(2) (4) (CH3)2C=CHCH2OH CH=CHCH3CH=CHCH(CH3)2 (5) CH3CH3CH3CH=CC=CHCH37.比较下列各组醇和溴化氢反应的相对速度。

解:(1) 反应速度顺序:对甲基苄醇 > 苄醇 > 对硝基苄醇。

(2) 苄醇 > β-苯基乙醇 > a-苯基乙醇。

8.(1) 3-丁烯-2-醇与溴化氢作用可能生成那些产物?试解释之。 解:反应产物和反应机理如下:

CH2=CHCHCH3OHCH2=CHCHCH3OHCH2=CHHBrCH2=CHCHCH3Br+BrCH2CH=CHCH3H+CH2=CHCHCH3+OH2+H2OCHCH3+CH2CH=CHCH3Br-BrCH2CH=CHCH3

Br-CH2=CHCHCH3Br (2) 2-丁烯-1-醇与溴化氢作用可能生成那些产物?试解释之。 解:反应产物和反应机理如下:

HOCH2CH=CHCH3HBrBrCH2CH=CHCH3+CH2=CHCHCH3OH

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有机化学课后习题答案

HOCH2CH=CHCH3H2O+H+H2OCH2CH=CHCH3CH2=CHCHCH3Br-CH2=CHCHCH3OH

++CH2CH=CHCH3Br-BrCH2CH=CHCH39. 应历程解释下列反应事实。 解: (1) 反应历程:

(CH3)3CCHCH3OHH+(CH3)3CCHCH3+H+(CH)CCH=CH332CH3CH3CHCH3C+CH3CH3CH3CCHCH3+H+CH3(CH3)2CHC=CH2CH3(2) 反应历程:

CH2OHH++(CH3)2C=(CH3)2

CH2++-HCH2CH2OH2+H2OCH2++H+CH2+H+CH3H+10. 用适当

地格利雅试剂和有关醛酮合成下列醇(各写出两种不同的组合)。 解:1.2-戊醇:

CH3CHO+CH3CH2CH2MgBrCH3CHCH2CH2CH3OMgBr

H2O.H+CH3CHCH2CH2CH3OH

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有机化学课后习题答案

CH3MgBr+OCHCH2CH2CH2CH3H2O.H+CH3CHCH2CH2CH3OMgBrCH3CHCH2CH2CH3OH

(2)2-甲基-2-丁醇:

CH3CH2MgBrCH3MgBr

+CH3COCH3+CH3COCH2CH3CH3CH3HO,H+2CH3CH2CCH3CH3CH2CCH3OHOMgBrCH3CH3HO,H+2CH3CH2CCH3CH3CH2CCH3OMgBrOH

(3)2-苯基-1-丙醇:

MgBr+OCHCH2CH3CHCH2CH3H3O+OMgBrCHCH2CH3OHCHO+CH3CH2CH2MgBrCHCH2CH3H3O+OMgBrCHCH2CH3OH

(4)2-苯基-2-丙醇:

CH3MgBr+CH3COC6H5MgBr+CH3CCH3H2O,H+OMgBrCH3+HO,H2CCH3OMgBrCH3CCH3OHCH3CCH3OH

CH3COCH3

11.合成题

解:(1)甲醇,2-丁醇合成2-甲基丁醇:

CH3CHCH2CH3PCl3CH3CHCHCH3Mg,(C2H5)2OCH3CHCH2CH3OHMgClCl

CH3OH[O]CH2O+H2O,H+CH3CHCH2CH3MgClCH3CH3CH2CHCH2OH

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有机化学课后习题答案

(2)正丙醇,异丙醇合成2- 甲基-2-戊醇

CH3CH2CH2OHCH3CHCH3OHCH3CH2CH2MgCl+CH3COCH3H2O,H+PCl3[O]CH3CH2CH2ClCH3COCH3CH3CH3CCH2CH2CH3OHMg,(C2H5)2OCH3CH2CH2MgCl

(3)甲醇,乙醇合成正丙醇,异丙醇:

PCl3CH3OHCH3OHCH3CH2OHCH3CH2OHCH3CH2MgClCH3MgCl+Mg,(C2H5)2OCH3ClCH3MgCl[O]PCl3[O]+CH2OCH2OCH3CH2ClCH3CHOMg,(C2H5)2OCH3CH2MgClH2O,H+H2O,H+CH3CH2CH2OHCH3CHCH3OHCH3CHO

(4)2-甲基-丙醇,异丙醇合成2,4-二甲基-2-戊烯

[O]CH3CHCH3CH3COCH3OHCH3CH3CH3Mg,(CH)OPCl3252CH3CHCH2MgClCH3CHCH2OHCH3CHCH2ClCH3COCH3

H2O,H+CH3CH3CH3CH3HSOCH3CHCH2CCH324CH3CHCH=CCH3OH

(5)丙烯合成甘油和三硝酸甘油酯

CH3CH=CH2

Cl2HOClClCHCH=CH225000CNaOH,H2OCH2CHCH2OHOHOHCH2CHCH2ClOHCl3HNO3Ca(OH)2

ClCH2CHCH2OH2SO4CH2CHCH2ONO2ONO2ONO2

(6)苯,乙烯,丙烯 合成3-甲基-1-苯基-2-丁烯

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有机化学课后习题答案

CH3CH=CH2+[O]CH3COCH3AlCl3CH2CH3-H2CH=CH2CH2=CH2HBr/ROORCH2CH2BrMg,(C2H5)2OCH3H2SO4CH2CH2MgClCH3CH2CH=CCH3+HO,HCH3COCH32CH2CH2CCH3OH下面转变。

解:(1) 乙基异丙基甲醇 2-甲基-2-氯戊烷

CH3CH3CH3CH2CHCHCH3HCl,ZnCl2CH3CH2CH2CCH3

OHCl

(2)3-甲基-2-丁醇 叔戊醇

CH3CH3CHHCH33CHCHCH32SO4CHH3CH=CCH32O,H+CH3CH2CCH3

OHOH

(3)异戊醇 2-甲基-2-丁烯

CH3CHCH2CH2OHH2O,H+CH3C=CHCH3

CH3CH3

13.用指定的原料合成下列化合物(其它试剂任选)。

解:

(1)(CH3)COH+HBr(CH3)3CBrMg,(C2H5)2O(CH3)3CMgBrCH2OCH2(CHH3)3CCH2CH2OMgBr2O,H+(CH3)3CCH2CH2OH

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12.完成

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