CH3CH2OH[O]CH3COOHNaBrH2SO4CH3CH2OHH+△CH3COOC2H5C2H5ONaH+CH3COCH2COOC2H5
(1)CH3CH2OHCH3CH2Br①C2H5ONa②C2H5Br①C2H5ONa②C2H5Br5%NaOHCH3COCH2COOC2H5CH3CH2CH(C2H5)COCH3
(2)CH3OHNaBrH2SO4CH3Br①C2H5ONa②CH3BrCH3COCH2COOC2H5[O]①C2H5ONa②CH3Br40%NaOH(CH3)2CHCOOH
(3)CH3CH2OHCH3COOHCl2PClCH2COOHCH3CH2OHH+ClCH2COOC2H5CH3COCH2COOC2H5H+①C2H5ONa②ClCH2COOC2H5CH2BrCH2Br5%NaOHCH3COCH2CH2COOH
(4)CH3CH2OHBr2- H2O2CH3COCH2COOC2H5NaBrH2SO4①2C2H5ONa②CH2BrCH2BrCH3CH2BrHCHOHBr过氧化物①Mg干醚+5%NaOHCH3COCH2CH2CH2CH2COCH3
(5)CH3CH2OHCH3OHCH3CH2MgBrCH3CH2CH2OHH+CrO3 / 吡啶Br2光①CH3CH2MgBr②H3O- H2OCH3CH=CH2BrCH2CH2CH2Br5%NaOHCH3COCH2COOC2H52C2H5ONa②BrCH2CH2CH2BrCCH3O
10、该化合物为：CH3COCH2CH2COOH 反应式略。 11、A: CH3CH2COOC2H5 B: CH3CH2COCH(CH3)COOC2H5
C: C2H5COC(C2H5)(CH3)COOC2H5 D: CH3CH2COCH(CH3)CH2CH3 反应式略。
第十五章 硝基化合物和胺
1、 （1）2-甲基-3-硝基戊烷 （2）丙胺 （3）甲异丙胺 （4）N-乙基间甲苯胺
（5）对氨基二苯胺 （6）氢氧化三甲基异丙铵 （7）N-甲基苯磺酰胺 （8）氯化三甲基对溴苯铵 （9）对亚硝基-N，N-二甲基苯胺 （10）丙烯腈
2、
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NHCOCH(1)NO23CH3(2)CH3NH2 ·H2SO4(3)NC2H5CH3NH2(4)CH2NH2(8)N=C=O
(5)CH2CH2CH2NH2CH2CH2CH2NH2(6)CH3NC(7)3、(1) ① Ag(NH3)2OH ② CHCl3/KOH (异腈反应) ③NaHCO3 溶液
NH2(2)CH3SO2Cl√√NaOHH2O溶解不溶解NHCH3N(CH3)2(3) CHCl3/KOH (异腈反应)
(4) Br2/H2O (或用漂白粉溶液，苯胺显紫色) 4、
×
CH3CH2CH2NH2(1)CH3CH2CH2NO2(CH3)3CNO2HCl√HO-溶解CH3CH2CH2NH2溶于水H+××NaOHH2OCH3CH2CH2NO2
不溶于水-H2N(2)COOHOHNH2NaOHH2O√溶于水√溶于水过量HCl溶于水HOH2NOHCOOH不溶于水×油
(3)(CH3CH2)3NH2O溶于水CH3CO(CH2)3CH3CH3(CH2)4CH2NH2CH3(CH2)4CH2OH5、（1）甲胺 ＞ 氨 ＞ 苯胺 ＞ 乙酰胺
×××NaHSO3√H+××H2O△CH3CO(CH2)3CH3溶于水HO-CH3(CH2)4CH2NH2
稀HCl不溶于水 （2）苄胺 ＞ 对甲苯胺 ＞ 对硝基苯胺 ＞ 2，4-二硝基苯胺 （3）甲胺 ＞ N-甲基苯胺 ＞ 苯胺 ＞ 三苯胺
NH2(4)∨NH2∨NHCOCH3(5)NH∨NH
6、（1）CH3CH2COOH , CH3CH2COCl , CH3CH2CON(CH2CH2CH3)2 , (CH3CH2CH2)3N
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H3C(2)CH3N+CH3HO-H3CCH3NCH2H3CCH3CH3N+；CH3；CH3CH2HO-CH2CH2H3CO(3)+N(CH3)3ONO+H2O
CH2C6H5CH2C6H5CH2C6H5NCH(COOC2H5)2；OC(COOC2H5)2；H2NC(COOC2H5)2；H2NCHCOOH
7、
(1)(CH3)2CHCH2CH2OH[O](CH3)2CHCH2COOHBr2NaOH①SOCl2②NH3
(CH3)2CHCH2CONH2PCl3(CH3)2CHCH2NH2NH3(2)(CH3)2CHCH2CH2OH(3)(CH3)2CHCH2CH2OH(CH3)2CHCH2CH2Cl(CH3)2CHCH2CH2Cl(CH3)2CHCH2CH2NH2
PCl3H2 , NiNaCN(CH3)2CHCH2CH2CN
(CH3)2CHCH2CH2CH2NH22NaCNH2 , Ni(4)CH2=CH2Br2BrCH2CH2BrCH3CH2Br2NaCNH2NCH2CH2CH2CH2NH2
(5)CH2=CH2HBr(6)CH3CH=CH2Br2NaCNH3O△+CH3CH2CN
HOOCCH2CH(CH3)COOHBr2
(7)8、
O2NCH3[O]①SOCl2②NH3HO-O2NNH2
CH3(1)混酸CH3KMnO4△COOHFe+HClCOOHNO2混酸NO2NO2(NH4)2SNH2
NO2(2)发烟H2SO4HNO3△NH2NO2NO2
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NO2NHCOCH(3)混酸Fe+HCl(CH33CO)2OHNO3(CH3CO)2ONHCOCH3NOH+NH23OFe+HCl2NH△2
CH3CH3CH3CH3(4)混酸Fe+HClH2SO4混酸O2NNO-2HOO2N△NO+2NH3OSO2HN+H3OSO2HNO2(5)混酸Fe+HClNH2SO2NHSO3HClSO3HNO2NO2
NO2(6)混酸Zn过量NHNHNaOH醇溶液
CH3CH3CH3混酸(7)Fe+HClNONHNHCH222CH3Cl2光CH2Cl
SO3HONa3(8)H2SO4CHOCH①NaSO3OCH33IBr2②NaOH熔融FeBr3①Mg 干醚①H+OCH3OOCH3O①NK3Br②O②PBr3OCH2CH2NH2②NaOHH2OCH2CH2Br
OCH3CH2BrNKCH2NH2CH+(CH(9)NBS①O3CH3Br2N3)3Br-②NaOHH2O
CH3NO2NH2
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CH3(10)混酸CH3[O]COOHSOCl2COClNO2NO2NO2AlCl3O2NCONHCOCH3混酸Fe+HClCH3COCl硝化还原乙酰化NHCOCH39、（3）的合成路线最合理。 10、略
11、A：CH2=CHCH2NH2 B：CH3CH2CH2CH2NH2 C：[CH2=CHCH2CH2N(CH3)3]+ I –
E:COOHD：CH2=CH—CH=CH2
COOH
CH2CH3CH2N12、该化合物为：
第十六章 重氮化合物和偶氮化合物
1、(1) 重氮苯硫酸盐 (2) 对乙酰基重氮苯盐酸盐 (3) 4-甲基-4’-羟基偶氮苯 (4) 4-(N,N-二甲胺基)-4’-甲基偶氮苯 (5) 2,2’-二甲基氢化偶氮苯 (6) 二氯碳烯
2、增强。因为苯基重氮盐是一种弱的亲电试剂，故当重氮基邻位或对位上连有强吸电子基硝基时，增强了重氮盐的亲电性，使偶合反应活性提高。3、重氮盐与苯胺偶合在弱酸中有利，重氮盐与酚偶合在弱碱中有利。
CH3CH3CH3CH34、(1)Fe，HCl；NaNO2，HCl；；；；；OHCH3BrCNHH2N3CNNCH3；F
OCH3CH3CH(2)3CH2CH2H(3)ClCl(4)HCH2CH2CH2CH3
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