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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