有机化学第二版 - - 徐寿昌 - 课后答案

(1)CH3CH2OHNaBrH2SO2H5)24CH3CH2BrC2H5ONaCH3OHNaBrH2SO4CH3BrCH2(COOC①C2H5ONa②CH3BrNaHC(COOC2H5)2C2H5BrC2H5CH(COOC2H5)2H+- CO△2H2OCH3CH2CH(CHO23)COOH

(2)CH3CH2OHH△+CH2=CH2AgH2COCH2H3O+CH3CH2OHNaBrH2SO4CH3CH2BrMg干醚CH3CH2MgBr

CH3CH2CH2CH2OHCH2(COOC2H5)2NaBrH2SOC2H5ONa4CH3CH2CH2CH2BrCH3CH2CH2CH2BrH+- CO△2H2OCH3CH2CH2CH2CH2COOH

+(3)CH3CH2OHLiAlH4NaBrH2SO4CH3CH2BrH△+NaCNCH3CH2CNCH2=CHCHHH2OBr2CH3CH2COOHCH3CH(Br)CH2BrCH3CH2CH2OH2C2H5ONa- H2O32Br2CH2(COOCH+2H5)22NaCH(COOC2H5)2CH3CH(Br)CH- CO2CH2CH2COOHH3CCHCH2COOH

H2O△1,2-二溴乙烷合成酮 (3).

(4)CH3CH2OH2CH2(COOCH△+- H2OCH2=CHBr22CH2BrCH2Br2H5)22Br2H5)22H5)22H5)22C2H5ONa2NaCH(COOCCH2BrCHCH2BrCH2BrCH2CH(COOCCH2CH(COOCC2H5OCO

2C2H5ONaCOOCCOOC2H52H5H+- CO△2C2H5OCOH2OHOOCCOOH

(5) 1,2-二溴乙烷合成同 (4).

2C2H5ONaCH2(COOC2H5)2CH2BrCH2BrCOOCCOOC2H52H5H+- CO△2H2OCOOH

9、乙酰乙酸乙酯合成:

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CH3CH2OH[O]CH3COOHNaBrH2SO4CH3CH2OHH+△CH3COOC2H5C2H5ONaH+CH3COCH2COOC2H5

(1)CH3CH2OHCH3COCHCH3CH2Br2H52COOC①C2H5ONa②C2H5Br①C2H5ONa②C2H5Br5%NaOHCH3CH2CH(C2H5)COCH3

(2)CH3OHNaBrH2SO4CH3Br①C2H5ONa②CH3BrCl2PCH3COCH2COOC2H5①C2H5ONa②CH3Br40%NaOH(CH3)2CHCOOH

(3)CH3CH2OH[O]CH3COOHClCH2COOHCH3CH2OHH+ClCH2COOC2H5CH3COCH2COOC2H5①C2H5ONa②ClCH2COOC2H55%NaOHCH3COCH2CH2COOH

(4)CH3CH2OHH+Br2- H2O2H5CH2BrCH2Br①2C2H5ONa5%NaOH2CH3COCH2COOC②CH2BrCH2BrMgCH3COCH2CH2CH2CH2COCH3

(5)CH3CH2OHCH3OHNaBrH2SOCH3CH2Br4干醚CH3CH2MgBrCH3CH2CH2OHH+CrO3 / 吡啶Br22HCHOHBr过氧化物2H5①CH3CH2MgBr②H3O+- H2OCH3CH=CH光BrCH2CH2CH2Br2C2H5ONa2CH2CH2BrCH3COCH2COOC①5%NaOHCOCH3

②BrCH10、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)NC2H5(4)CH2NH2CH3(5)CH2CH2CH2NH2CH2CH2CH2NH2(6)CH3NC(7)NH2(8)N=C=O

3、(1) ① Ag(NH3)2OH ② CHCl3/KOH (异腈反应) ③NaHCO3 溶液

NH2(2)CH3SO2Cl√3NaOHH2O溶解不溶解NHCH√N(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)3CNO2√HClHO-溶解NaOHH2OCH3CH2CH2NH2溶于水H+××CH3CH2CH2NO2

HO-不溶于水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)4CH2OH5、（1）甲胺 ＞ 氨 ＞ 苯胺 ＞ 乙酰胺

××稀HClHOCH3(CH2)4CH2NH2

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-H3CCH3NCH2H3CCH3N+CH3CH2HO-；CH3；CH3CH2CH2H3C+N(CH3)3+H2O

O(3)NCH(COOCO7、

[O]2H5)2OCH2C6H5C(COOC2H5)2CH2C6H5CH2C6H5；NO；H2NC(COOC2H5)2；HNCHCOOH2

(1)(CH3)2CHCH2CH2OH(CH3)2CHCH2COOH2①SOCl②NH32(CH3)2CHCH2CONHPClBr2NaOH(CH3)2CHCH2NH2NH

(2)(CH3)2CHCH2CH2OH3(CH3)2CHCH2CH2Cl3(CH3)2CHCH2CH2NH2

(3)(CH3)2CHCH2CH2OHPCl3(CH3)2CHCH2CH2ClNaCN(CH3)2CHCH2CH2CN

H2 , Ni(CH3)2CHCH2CH2CH2NH22NaCNH2 , Ni(4)CH2=CH2Br2BrCH2CH2BrH2NCH2CH2CH2CH2NH2

(5)CH=CH22HBrCH3CH2Br2NaCNNaCNCH3CH2CN+

(6)CH3CH=CHBr22H3O△HOOCCHBr22CH(CH3)COOH

(7)8、

O2NCH3[O]①SOCl②NH32HO-O2NNH2

CH3混酸CH3KMnO△4COOHFe+HClCOOH(1)NO2NO2(2)混酸NO2NO2(NH4)2SNH2

NH2NO2发烟HNOH2SO34△NO2

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