有机化学课后习题答案南开大学版17章胺

1第十七章胺1．命名下列化合物：（1）N-甲基-N-乙基苄基胺；（2）1，2-环己二胺；（3）2-甲基-4-丙氨基戊烷；（4）4-氨基戊醛；（5）N-甲基间甲苯胺；（6）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)2NCNCN(CH3)2N3．分别比较下列各组化合物的碱性：（1）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（2）氢氧化四甲铵苄胺苯胺N-乙酰苯胺（3）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：稀CH3CH3(CH3CH2)2NCH2CNHOCH3CH3(CH3CH2)2NCH2CNHOHSO4-H+H2SO4CH3CH3(CH3CH2)2NCH2CNHOCH3CH3H2NH+HCl稀(CH3CH2)2NCH2COOHCl-+CH3CH3(CH3CH2)2NCH2CNHOCH3CH3H2N稀(CH3CH2)2NCH2CO2-+NaOH5．完成下列反应式：(1)O2NClClNa2CO3H2OO2NClOH(2)H+CH3NO2ZnNaOHNHNHCH3CH3NH2CH3CH3H2N(3)ClO2NNO2ClNH4SHClO2NNH2Cl+(4)CH3CH2NO2CH3CH2CHOOH-H2/PtCH3CH2CH=CNO2CH3CH3CH2CH2CHNH2CH3+(5)CH3NO2OH-HCHO3HOCH2CCH2OHNO2CH2OHO+(6)(CH3)2CHNH2(CH3)2CHNHCH2CH2OH2+(7)NHBr(CH2)4BrNBr-+(8)CH3IAg2O过量NHCH3H3CNCH3CH3CCHC6H5OCH3(9)H+C6H5CCH3OHCHCH3NH2NaNO2(10)KOHNHOOCH3CHCOOC2H5ClNH2NH2CH3CHCOOHNH2+H+(11)NaNO2OHCH2NH2OO+(12)C6H5COCH2CH3HCHO(C2H5)2NH+C6H5COCHCH2N(C2H5)2CH3Br2NaOH(13)H+NaNO2NHOOCOO-NH2KICOOHIBr2(14)CONH2NH2(15)CH2CNNH3H2/NiCH2CH2NH2CH3COClLiAlH4CH2CH2NHCH2CH3(16)CH2N=C=OCH3OHCH2NHCOOCH3(17)OH(NH4)2SO3NH2压力H2OH+(18)ONH+NCH2=CHCNOCH2CH2CN(19)NCH3CH3H2O2OHNCH3CH3(20)CH2NH2NaNO2HCl(H2O)CH2OH(21)CH2CH2CNOH2/PtNH36．用简单化学方法分别鉴别下列两组化合物：SO2Cl不反应C6H5NH2C6H5CH2NH2C6H5N(CH3)2C6H5CH2N(CH3)2沉淀沉淀不反应Br2H2OBr2H2O白色沉淀白色沉淀无沉淀无沉淀（1）HClNaNO2SO2Cl不反应不溶于NaOH水溶液沉淀沉淀CH3NH2NHCOCH3CH2NHCH2CH3CH2CH2NH2沉淀NaOH/H2O溶于NaOH水溶液溶于NaOH水溶液2-萘酚红色气体(2)7．用化学方法分离下列混合物：NaOHCH2OHOHCH3CH2NH2NaOH/H2O(1)NHCH3水层油层ONaCH3HCl/H2O水层油层CH2OHCH2NH3Cl-NH2CH3Cl-++水层SO2Cl水层油层NSO2CH3CH2NSO2NaH3O+H3O+中和中和CH2NH2NHCH3CH3OHCH2CH3NH2CH3NHCH3NaHCO3(2)水层油层HCl/H2O水层油层NH3Cl-CH3++水层油层COOHOHCOONaOHNaOH1)2)H+CH3ONaH3O+CH3OHCH2CH3NH2CH3Cl-NaOH水层SO2ClNSO2CH3NSO2NaH3O+H3O+中和中和NH2CH3水层油层NHCH348．写出下列反应的机理：H2OHR'NRCOOCO碱R'NRCOOCORCOO-RN=C=O+RN=C=ORNHC=OOHRNH2CO2+9．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。FeHNO3H2SO4KMnO4HCl(1)CH3CH3O2NCOOHO2NCOOHH2NCl2(2)CH3hvCH2ClHN(CH3)2CH2N(CH3)2(3)COCH3CH3COClAlCl3NH3H2/PdCHNH2CH3FeEt2OOH2OCH2CH2OHBr(4)NH3H2/PdBr2MgN.CrO3CH2CHOCH2CH2NH2H2/NiCHO(5)CHCH2NH2OHCO,HClZnCl2CHCNOHHCNHNO3H2SO4CH3(6)CH3NO2H+ZnNaOHNHNHCH3CH3NH2CH3CH3H2N10．完成下列转化：(1)COOHCOOHNCH3OOCH3NH2LiAlH4NCH3H2OCH2COOHCH2NH2(2)H+CH2CCH2ONH2OHCH2CCH2NOHCH2CNHCH2O+PCl3(3)NH3CHCOOHCHCOClBr2/OH-CHCONH2CHNH2CH3COClH2OFeCH3O2N(4)Br2HClCH3H2NCH3CH3COCHNBrOH-CH3H2NBr5H+H2OH+(5)ONHNCH2=CHCH2ClOCH2CH=CH2phCO3HOCH2CHCH2OLiAlH4(6)CH3CH2COClC6H5NHCH3CH3CH2CONC6H5CH3CH3CH2CH2NC6H5CH3H2SO4NaOH(NH4)2SO3(7)SO3HOH熔融压力NH211．根据下列反应写出各化合物的结构：(1)(2)Br2(1)LiAlH4H+NCH3ONCH3HONCH3CH3I过量NCH3CH3+I-AgOHN(CH3)2ABCDEFGCH3I(1)(2)AgOHBrBr(1)(2)过量(CH3)2NHCH3IN(CH3)3I-N(CH3)3I-++(1)(2)AgOH(2)CH3I过量ABCDCH3IAgOHAgOHNCH3CH3CH2CH3CH2=CH2+NCH3CH3CH3NCH3CH3CH3CH3CH3IAgOHCH3CH3++(CH3)3NO3Zn/H2OHCHOCH3COCOCH3212．Prolitane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：Cl2C2H5ONahvCH3CH2COCl(1)H+H2ONHCH3CH2ClMgEt2OCO2C2H5OHH+CH2COOC2H5CHCOCH2CH3COOC2H5OH-CH2COCH2CH3H2/PdN(2)H+FeHNO3H2SO4KMnO4HClCH3CH3O2NCOOHO2NCOOHH2NHOCH2CH2N(CH3)2COOCH2CH2N(CH3)2H2NCH3(CH2)3BrCOOCH2CH2N(CH3)2CH3(CH2)3NH13．通过重氮盐完成下列转化：H2SO4CH3COCl(1)H2OOH-HNO3BrNH2BrNHCOCH3BrNH2NO2NaNO2HBrCu2Br2BrNO2Br6(2)CH3NO2FeKMnO4HClNaNO2HBrCu2Br2COOHNO2COOHNH2COOHBr(3)H2/PdKMnO4NH2CH3NaNO2HClCuCNCH3CNCOOHCNCOOHCH2NH2NaNO2HClCuCNHNO3H2SO4CH3(4)CH3NO2H+ZnNaOHNHNHCH3CH3NH2CH3CH3H2NCNCH3CH3CNFeHClNaNO2COOHNO2H2SO4(5)COOHNH2HBF4COOHFPCl3NH3Br2/OH-CONH2FFNH214．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：AlCl3NaOHHgZn浓(1)熔融H2SO4HClOHCH3CH2COClOCCH2CH3OCOCH2CH3HOCH2CH2CH3HOH2SO4AlCl3HgZn浓H2OH+FeHNO3H2SO4HClNaNO2HClCH3CH2COClCOCH2CH3CH2CH2CH3HOCH2CH2CH3CH2CH2CH3O2NCH2CH2CH3H2N或(2)H2OFeHNO3H2SO4HClNaNO2HClCH3COClNO2NH2HNO3H2SO4NHCOCH3NO2OH-Br2BrBrNH2NO2H3PO2BrBrNO2FeHClBrBrNH2(3)HNO3H2SO4HClNaNO2Br2H3PO2FeHClCH3CH3NO2CH3NH2CH3NH2BrBrCH3BrBr7(4)HClNaNO2Br2/OH-O2V2O5NH3OOONHOOCOO-CONH2KICOOHI(5)HNO3H2SO4CH3CH3NO2NH3NBSCH2BrNO2CH2NH2NO2H2O(6)HNO3H2SO4NO2NH2Br2FeHClHClNaNO2H3PO2BrBrNH2BrBrBrBrHCl(7)CH3COClBr2H2OFeHNO3H2SO4NaNO2HClNO2NH2HNO3H2SO4NHCOCH3OH-BrBrNH2NO2H3PO2FeHClNHCOCH3O2NNH2O2NHBrCu2Br2BrBrNO2BrBrBrNH2BrNaNO2BrBrBrNaNO2HClCuCNHNO3H2SO4CH3(8)CH3NO2H+ZnNaOHNHNHCH3CH3NH2CH3CH3H2NCNCH3CH3CNH3+OCOOHCH3CH3HOOCHNO3H2SO4CH3(9)CH3NO2FeKMnO4HClNaNO2HBrCOOHNO2COOHNH2COOHN2+Cl-OHpH=8COOHN=NOHH2OFeHNO3H2SO4HClNO2NH2H2SO4HNO3H2SO4(10)FeHClNaNO2HBrpH=8NH2HO3SN2+Cl-HO3SNH2NaHSO3OHN=NHOSO3H15．多巴胺（Dopamine）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，怎样由生物碱——tyramine合成Dopamine？8H2/PdH2SO4H2OH+HNO3H2SO4NaNO2CH3COClCH2CH2NH2HOCH2CH2NHCOCH3HOCH2CH2NHCOCH3HOH2NCH2CH2NH2HOHOTyramineDopamine16．叶酸可由下列反应制备，写出反应机理：H2ONNOHNH2NH2H2N+Br2CHCOCH2BrHBrNNOHNHNH2H2NCHCOCH2BrBrHBrCHCOCH2BrNNOHNNH2H2NNNOHH2NNHNOHCH2BrNNOHH2NNNCH2BrCONHCHCH2CH2COOHCOOHH2NNNOHH2NNNCH2NHCONHCHCH2CH2COOHCOOHNaHCO3/H2O叶酸（folicacid）17.(1)H2NCOOHABCHOCH2CH2N(C2H5)2CH3COOCH2CH2N(C2H5)2H2NCOOCH2CH2N(C2H5)2奴弗卡因(2)H+FeHNO3H2SO4KMnO4HClCH3CH3O2NCOOHO2NCOOHH2NHOCH2CH2N(CH3)2COOCH2CH2N(CH3)2H2N18.ABCCONCH3ClCOClOHNHCH3HClCOClNH2ClNH2CD19.20.CH2NCH2CH3N(CH2CH3)221.ABCHN(CH2CH3)2DCH3CH2N(CH3)2(CH3)3CNH2(CH3)2CHCH2NH222.H2NCH323.CH3CH2CHCH3NH2