CH3CH2CH2NH2(1)CH3CH2CH2NO2(CH3)3CNO2√HClHO-溶解NaOHH2OCH3CH2CH2NH2溶于水H+××CH3CH2CH2NO2不溶于水
HO-H2N(2)COOHOHNH2NaOHH2O√溶于水√溶于水过量HCl溶于水H2NOHCOOH不溶于水×油
(3)(CH3CH2)3N2)3CH3溶于水H2OCH3CO(CH×××NaHSO3√H+H2O△CH3CO(CH溶于水2)3CH3-CH3(CH2)4CH2NH2CH3(CH2)4CH2OH××稀HClHOCH3(CH2)4CH2NH2不溶于水
5、（1）甲胺 ＞ 氨 ＞ 苯胺 ＞ 乙酰胺
（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
H3C(2)CH3CH2CH2H3CN+CH3HO-H3CCH3NCH2H3CCH3N+CH3CH2HO-；CH3；CH3+N(CH3)3+H2O
CH2C6H5CH2C6H5O(3)NCH(COOCO2H5)2OCH2C6H5C(COOC2H5)2；NO；H2NC(COOC2H5)2；HNCHCOOH2
7、
(1)(CH3)2CHCH2CH2OH[O](CH3)2CHCH2COOH2①SOCl②NH32(CH3)2CHCH2CONHPClBr2NaOH(CH3)2CHCH2NH2NH
(2)(CH3)2CHCH2CH2OH3(CH3)2CHCH2CH2Cl3(CH3)2CHCH2CH2NH2
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(3)(CH3)2CHCH2CH2OHPCl3(CH3)2CHCH2CH2ClNaCN(CH3)2CHCH2CH2CNH2 , Ni(CH3)2CHCH2CH2CH2NH22NaCNH2 , Ni
(4)CH2=CH2Br2BrCH2CH2BrH2NCH2CH2CH2CH2NH2(5)CH=CH22HBrCH3CH2Br2NaCNNaCNCH3CH2CN+
(6)CH3CH=CHBr22H3O△HOOCCHBr22CH(CH3)COOH(7)O2NCH3[O]①SOCl②NH32HO-O2NNH2
8、
CH3混酸CH3KMnO△4COOHFe+HClCOOH(1)NO2NO2(2)混酸NO2NO2(NH4)2SNH2
NH2NO2发烟HNOH2SO34△NO2
(3)混酸NO2Fe+HCl(CH3CO)2ONHCOCH3HNO32O(CH3CO)NHCOCHNO23H3O△+NH2Fe+HClNH2
CH3Fe+HClCH3(4)混酸CH3H2SO4CH3混酸△O2N+NO2NH3OSOHO-CH3O2NNO2NH2NO2NH3OSO+2H2H
NO2(5)混酸Fe+HClNH2SO2NHSO3HClSO3HNO2NO2
NHNHNO2(6)混酸Zn过量NaOH醇溶液
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CH3混酸CH3Fe+HClCH3(7)NOCl2NHCH2NH2CH2ClCH32光
ONaOCHCH3IO3SO3H(8)H2SO4OCHBr2FeBr33①NaSO3②NaOH熔融①Mg 干醚②O①H3O②PBr+OCH3OCH①3NKO3BrCH2CH2NH2②NaOHH2OCH2CH2Br
OCH3(9)NBSCH2Br①②NaOHNKOH2OCH2NH23CH3BrCH2N(CH3)3Br-+
COCl2CH3(10)混酸CH3[O]COOHSOClNO2混酸硝化NO2CH3COCl乙酰化NO2NHCOCHAlCl3COO2NNHCOCH3Fe+HCl还原3
9、（3）的合成路线最合理。 10、略
11、A：CH2=CHCH2NH2 B：CH3CH2CH2CH2NH2 C：[CH2=CHCH2CH2N(CH3)3]
D：CH2=CH—CH=CH2
E:COOHCOOH+ –
I
CH2CH312、该化合物为：
CH2N
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。
CH34、(1)Fe，HCl；NaNO2CH3CH3CH3，HCl；OH；CH3；Br；CN；H3CH2NNNCH3；F
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OCH(2)3CH3(3)ClCl(4)CH3CH2CH2HCH2HCH2CH2CH3
5、(1)(2)(3)重氮组分HO3SNNN2+偶氮组分+N(CH3)2OH重氮组分N2N2N2++偶氮组分重氮组分CH3CONHNa2O3SN2+偶氮组分偶氮组分HOOHNH2CH3(4)重氮组分(5)重氮组分N2+偶氮组分SO3H
ClNO26、(1)Fe，HClFeClCl23ClNH2ClNaNO24ClC2H5OHClH2SOCl
CH3CH3(2)混酸Fe，HClCH3FeBrBr23CH3NaNO24C2H5OHBrNH2BrH2SONH2BrBr
NO2(3)混酸发烟H2SOHNO34NH2Fe，HClNaNO2CNKCNNO2NH2HClCN
NHCOCH(4)3Br2H3O+NH2①NaNO②H2O2OH，H2SO4BrCH3，△BrCH3(5)混酸Fe
+CH3，HClNH2CH3①NaNO②2(CH3CO)2OHNO3H3OH2SO4，NO2NHCOCH33C2H5OHNO2
BrBrNH2(6)(CH3CO)2ONHCOCH混酸Br2FeBr3BrNHCOCHBr3H3O+①NaNO②2，H2SO4NO2NO2C2H5OHNO2
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NH2(7)(CH3CO)2ONHCOCH混酸3Br2FeBrBr3NHCOCHBr3H3O+BrNH2BrNO2①NaNO②KCN2NO2①NaNO②H2，NO2COOH2SO4HCl，H3O+COOHBrBrFe+HClNO2BrBr，CuCNC2H5OH
COOHNH2(8)CH3NO7、(1)混酸2CN①NaNO②KCN2HClH3O△+[O]，CuCNCH3COOHNH22CH3OH
3)2N(CHFe，HClN2ClNaNOHCl2，弱酸性NNN(CH3)2
CH3(2)混酸Fe，HClCH3NaNOHCl2，CH3NH2NO混酸发烟H2SOHNO34N2ClFe，HCl弱酸性NH2NH3CNNH22NH2NH2NO2
CH3(3)H2SO4CH3Na2SO3CH3①NaOH，熔融②H+SO3H混酸H3O△+①Fe，HCl②NaNOHCl2，OHCH3N2Cl弱碱性CH3NNHOCH3
N2ClNH2(4)混酸Fe，HClH2SO4180℃～190℃NSO3H弱碱性NOHHO3SH2SO4Na2SO3①NaOH，熔融②H+OH∧80℃
NHCOCH(5)混酸Fe，HClCH3COCl混酸CH3COOH混酸Fe，HCl2CH3OH3+N2ClHCl2，①H3O②NaNON(CH3)2NO2弱酸性N2ClN(CH3)2NNNO2O2N
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