有机化学课后习题答案 南开大学7章 胺.docx

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1、有机化学课后习题答案 南开大学7章 胺第十七章 胺 1命名下列化合物： N-甲基-N-乙基苄基胺； 1，2-环己二胺； 2-甲基-4-丙氨基戊烷；4-氨基戊醛； N-甲基间甲苯胺；二甲基环己胺氢溴酸盐 2比较下列化合物偶极距的大小： (CH3)2N(CH3)2NCNCN3分别比较下列各组化合物的碱性： 二乙胺乙胺对甲氧基苯胺苯胺对氯苯胺对硝基苯胺2，4-二硝基苯胺 氢氧化四甲铵苄胺苯胺N-乙酰苯胺 环己胺环己酮亚胺邻苯二甲酰亚胺 4预言下列化合物的反应： OCH3H2SO4稀(CH3CH2)2NCH2CNHCH3H(CH3CH2)2NCH2CNH+OCH3HSO4-CH3OCH3稀HCl(CH

2、3CH2)2NCH2CNHCH3H(CH3CH2)2NCH2C+OCH3OHCl-+H2NCH3OCH3NaOH稀CH3(CH3CH2)2NCH2CO2-(CH3CH2)2NCH2CNHCH3+H2NCH35完成下列反应式： Cl(1)O2NClNa2CO3H2OClO2NOHNO2(2)CH3ZnNaOHNHNHCH3CH3H+H2NCH3NH2CH3NO2(3)O2NClClNH4SHNH2O2NClClCH3-CH3H2/Pt(4)CH3CH2NO2+CH3CH2CHOOH-OHCH3CH2CH=CNO2CH3CH2CH2CHNH2CH2OH(5)CH3NO2+3HCHOHOCH2CNO

3、2CH2OH(6)(CH3)2CHNH2+O(CH3)2CHNHCH2CH2OH 1 (7)NH+Br(CH2)4BrN+Br-CH3(8)NHCH3I过量Ag2OH3CNCH3CH3(9)C6H5COHO(10)NHOKOHOCHCH3NH2ClCH3CHCOOC2H5NH2NH2NaNO2H+CH3CCHC6H5CH3NH2CH3CHCOOHO(11)OHCH2NH2ONaNO2H+(12)C6H5COCH2CH3+HCHO+(C2H5)2NHC6H5COCHCH2N(C2H5)2CH3O(13)NHOBr2NaOHCOO-COOHNaNO2H+KINH2I(14)CONH2Br2NH2(

4、15)CH2CNH2/NiNH3CH2CH2NH2CH3COClLiAlH4CH2CH2NHCH2CH3(16)CH2N=C=OCH3OHCH2NHCOOCH3(17)OH(NH4)2SO3压力NH2O(18)+OH+NCH2=CHCNH2OCH2CH2CNNHCH3(19)NCH3H2O2CH3NCH3OH(20)CH2NH2NaNO2HCl(H2O)CH2OHCH2CH2CN(21)OH2/PtNH 2 6用简单化学方法分别鉴别下列两组化合物： C6H5NH2沉淀Br白色沉淀2CH2O无沉淀6H5CH2NH2SO2Cl沉淀C6H5N(CH3)2不反应Br2白色沉淀C6H5CH2N(CH3)

5、2不反应H2O无沉淀CH3(2)NH2沉淀溶于NaOH水溶液NaNO22-萘酚HClCH2CH2NH2SO液2Cl沉淀溶于NaOH水溶NaOH/H2OCH2NHCH2CH3沉淀不溶于NaOH水溶液NHCOCH3不反应7用化学方法分离下列混合物： (1)CH2NH2水层CH3ONaNHCH3NaOH/H2O油层CH2OHCH2OH油层HCl/H2O+CH水层CH2NH3Cl-NH2CH3Cl-3OHCH3O+中和SO2Cl油层NSOH32NHCH3水层NaOH水层CHH3O+中和2NSO2CH2NH2NaCH3(2)OHCOONaCOOH水层OHOHCH3CH3NaHCO3水层ONaH3O+OH

6、NHCH3油层1)NaOHCH2)H+CH3NH2油层2CH3HCl/HO油层2CH+3NH3Cl-CH2CH3水层+NH2CH3Cl-CH33O+中和NHCHSO32Cl油层NSOH2水层NaOHNa水层NSOH3O+中和2CH3NH2 3 红色气体8写出下列反应的机理： ORCHNOOCH2OORR碱ONOCRRCOO-RC=OOC+RN=C=ORN=C=ONHRNH2+CO2H9由甲苯、苯和不超过四个碳的醇及必要的无机试剂合成下列化合物。 (1)CH3HNO3H2SO4O2NCH3KMnO4O2NCOOHFeHClH2NCOOH(2)CH3Cl2hvCH2ClHN(CH3)2CH2N(C

7、H3)2(3)CH3COClAlCl3COCH3NH3H2/PdCHNH2CH3N. CrO3(4)FeBr2BrMgEt2OOH2OCH2CH2OHCH2CHONH3H2/PdCH2CH2NH2OH(5)CO,HClZnCl2OHH2/NiCHOHCNCHCNCHCH2NH2CH3(6)CH3HNO3H2SO4NO2ZnNaOHNHNHCH3CH3H+H2NCH3NH2CH310完成下列转化： COOH(1)COOHCH3NH2ONCH3OONOHNH2OHLiAlH4NCH3H+OCH2CNHCH2(2)CH2CCH2CH2CCH2H2OCH2COOH+CH2NH2COOH(3)CHPCl

8、3COClCHNH3CONH2CHBr2/OH-NH2CHBr(4)O2NCH3FeHClBrCH3OH-H2OH2NCH3CH3COClBr2CH3COCHNH2NCH3 4 O(5)NHONCH2=CHCH2ClH2OH+CH2CH=CH2OphCO3HOCH2CHCH2H+CH3(6)CH3CH2COClC6H5NHCH3CH3LiAlH4CH3CH2CONC6H5SO3HCH3CH2CH2NC6H5OH(7)H2SO4NaOH熔融(NH4)2SO3压力NH211根据下列反应写出各化合物的结构： LiAlH4H+CH3NCH3CH3I过量+N(1)ONCH3NCH3HOACH3I-(1)

9、AgOH(2)BBrCN(CH3)3 I(1)过量(CH3)2NH(2)CH3I+-D(1)AgOH(2)N(CH3)2(1)CH3I(2)AgOHBr2EFBrGN(CH3)3 I-CH3CH3CH3(2)NCH3CH3I过量AgOHCH3CH2=CH2+CH3CH3IAgOHNCH3BOCH3NCH3COCCH3Zn/H2OCH2CH3AAgOHO3CH3I(CH3)3N+2HCHO+CH3CCH3DCH312Prolitane是抗抑郁药物，Tetracaine是麻醉药物。试从苯、甲苯和不超过4个碳的有机原料及必要的无机试剂设计合成路线： (1)CH3Cl2hvCH2ClMgEt2OCO2

10、C2H5OHH+CH2COOC2H5C2H5ONaCH3CH2COClCHCOCH2CH3COOC2H5OH-H2OH+CH2COCH2CH3NHH2/PdN(2)CH3HNO3H2SO4O2NCH3KMnO4O2NCOOHFeHClH2NCOOHHOCH2CH2N(CH3)2H+H2NCOOCH2CH2N(CH3)2CH3(CH2)3BrCH3(CH2)3NHCOOCH2CH2N(CH3)213通过重氮盐完成下列转化： Br(1)NH2CH3COClBrH2SO4HNO3OH-H2OBrNaNO2HBrCu2Br2BrNO2NHCOCH3NH2BrNO2 5 NO2(2)CH3KMnO4NO

11、2COOHFeHClNH2COOHNaNO2HBrCu2Br2BrCOOHCH3(3)NH2NaNO2HClCuCNCH3KMnO4COOHH2/PdCOOHCNCNCH2NH2CH3(4)CH3HNO3H2SO4NO2ZnNaOHNHNHCH3CH3H+H2NCH3NH2CH3NaNO2HClCuCNCNCH3CNCH3COOH(5)FeHClCOOHNaNO2H2SO4HBF4COOHPCl3NH3CONH2Br2/OH-NH2NO2NH2FFF14由苯、萘、甲苯及不超过4个碳的有机原料和必要的无机试剂合成下列化合物： H2SO4NaOH熔融CH3CH2COClOOCCH2CH3(1)OH

12、AlCl3HOCOCH2CH3ZnHg浓HClHOCH2CH2CH3CH3CH2COClAlCl3ZnHgH2SO4HNO3或COCH2CH3浓HClCH2CH2CH3O2NCH2CH2CH3FeHClH2NCH2CH2CH3NaNO2H2SO4H+H2OHOCH2CH2CH3(2)H2SO4HNO3NO2FeHClNH2CH3COClH2SO4HNO3NO2NHCOCH3NH2OH-Br2BrBrNaNO2HClH3PO2BrBrFeHClBrBrH2ONO2NO2NH2CH3(3)H2SO4HNO3CH3FeHClCH3Br2CH3NaNO2HClH3PO2CH3BrNO2NH2NH2Br

13、BrBr 6 O(4)O2V2O5ONH3OOCOOHNHOBr2/OH-COO-CONH2NaNO2HClKIICH2BrNBSNH3CH3(5)H2SO4HNO3CH3CH2NH2NO2NO2NO2NH2BrBrNaNO2HClH3PO2BrBr(6)H2SO4HNO3NO2FeHClNH2Br2H2OBr(7)H2SO4HNO3BrNHCOCH3H2SO4HNO3NO2FeHClNH2CH3COClNH2O2NNHCOCH3BrBrFeHClOH-H2OBrBrNaNO2HBrCu2Br2BrO2NNH2BrBr2BrBrBrNaNO2HClH3PO2NO2BrNO2BrNH2CH3NO

14、2(8)CH3HNO3H2SO4ZnNaOHNHNHCH3CH3H+H2NCH3NH2CH3NaNO2HClCuCNCNCH3CNCH3H3+OHOOCCH3COOHCH3NaNO2HBrNO2(9)CH3HNO3H2SO4-NO2COOHFeHClNH2COOHCH3KMnO4N2Cl+COOHOHCOOHpH=8N=NOHFeHCl(10)H2SO4HNO3NO2NH2H2SO4HO3SNH2NaNO2HBrHO3SN2Cl+-NH2HNO3H2SO4FeHClNaHSO3H2OOHpH=8HON=NSO3H15多巴胺是存在于中枢神经及其辐射系统的化学物质，若缺少它会得震颤性麻痹症，怎样由

15、生物碱tyramine合成Dopamine？ 7 HOCH2CH2NH2TyramineCH3COClHOCH2CH2NHCOCH3H2SO4HNO3H2/PdH2NHOCH2CH2NHCOCH3NaNO2H2SO4H+H2OHOHOCH2CH2NH2Dopamine16叶酸可由下列反应制备，写出反应机理： BrH2NNOHOH2NNOHNNCHCCH2BrH2NNNH2OHNNOHNHCH2BrH2OOCCH2BrHBrNNH2+NH2Br2CHOCCH2BrHBrH2NNNNHCHNH2OHH2NNOHNNNCH2BrH2NCONHCHCH2CH2COOHCOOHH2NNNNNaHCO3/

16、H2ONOHCH2NHCONHCHCH2CH2COOHCOOH叶酸17.(1)AH2NCOOHBHOCH2CH2N(C2H5)2CCH3COOCH2CH2N(C2H5)2奴弗卡因H2NCOOCH2CH2N(C2H5)2(2)CH3HNO3H2SO4O2NCH3KMnO4O2NCOOHFeHClH2NCOOHHOCH2CH2N(CH3)2H+H2NCOOCH2CH2N(CH3)2O18.AClCOCClCCH3NBClOCOHCNHCH3HClNH2DClNH2CH2CH319.CH2N20.N(CH2CH3)221.AHN(CH2CH3)2BCH3CH2N(CH3)2C(CH3)3CNH2D(CH3)2CHCH2NH2NH222.H2NCH323.CH3CH2CHCH3 8