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第2章烷烃1.解:(1)2,3,5,5-四甲基庚烷;(3)2,6-二甲基-4-乙基庚烷;(5)3-甲基-4-乙基庚烷2.解:CH3CH3(1)CH3CCH3;(3)CH3CH2CH2CHCH2CH2CH3;(5)CH3CCH2CHCH3CH3C(CH3)3CH3CH33.解:ClHHClHHHHHHClCl最稳定构象最不稳定构象5.解:(2)(b)>(d)>(e)>(a)>(c)6.解:按稳定性由大到小排列有:(3)>(2)>(1)。第3章烯烃和二烯烃1.解:(2)(E)-2-溴-2-戊烯;(4)4-甲基-3-乙基-1-戊烯;(6)(Z)-3,6,6-三甲基-4-异丙基-3-庚烯2.解:CH3(1)CH3C=CH2;(4)C=CCH3CH2CH3HCH2CH2CH34.解:CH3CH3(1)CH3CCH3;CH3CHCH2Br;(2)CH2CH2CHCH2Cl;(3)CH3CH2CH2CH2OH;(4)CCl3CH2CH2I(反马氏规则产物)BrOH(5)CH3CH2COOH;(6)CH3CHCH=CH2;CH3CHCHCH2ClClClCl5.解:(1);(2)H2/Lindlar催化剂;H2/Ni;(3)BrBr(4)由于中间体,有4种形式:CH3CCH=CH2CH2=CCHCH3CH3C=CHCH2CH2C=CHCH3CH3CH3CH3CH3(A)(B)(C)(D)BrCH3CCH=CH2CH3++++其中(A)最稳定。故主要产物为:(5)由于中间体,有2种形式:CH3CH=CHCHCH2CH3CH2CHCH=CHCH2CH3++稳定性,不好评价。故此有2种产物。BrBrCH3CH=CHCHCH2CH3CH2CHCH=CHCH2CH3(A)(B)(6)OCCO=O(7)CH3CH3COOCH3COOCH3COCH3Br(8);BrCOCH3=6.解:(3)>(2)>(5)>(4)>(1)9.解:(1)丙烯醛大于丙烯。(亲双烯体具有吸电子基团是有利于方应进行。醛基是吸电子基团。)(2)2-甲基-1,3-丁二烯大于1,3-丁二烯。(双烯体具有供电子基团是有利于双烯合成方应进行,甲基是供电子基团。)10.解:HBr(1)CH3CH=CH2CH3CHCH3BrCl2Cl2(3)CH3CH=CH2CH2CH=CH2CH2CHCH2hvClClCl(BH3)2H2O2/OH-(5)CH3CH=CH2CH3CH2CH2OH11.解:++甲基迁移H+(CH3)3CCH=CH2(CH3)3CCHCH3(CH3)2CCH(CH3)2H3O+(CH3)3CCH2CH2OHH3O+(CH3)3CCHCH3OHH3O+(CH3)2CCH(CH3)2OH(CH3)3CCH2CH2OH属于反马氏规则产物,难于生成。13.解:(a)CH3CH=CCH2CH3(b)CH3CH2CH=CHCH2CH3CH3反应的各步方程式:OOOO3Zn/HO2CH3CH=CCH2CH3CH3CHCCH2CH3CH3CHO+CH3CCH2CH3乙醛甲乙酮OCH3CH3(a)KMnO4CH3CH2CH=CHCH2CH32CH3CH2COOH(b)第4章炔烃3.解:BrClOCHCH333;(5)CH3CH2CCH3(1)CH3CCH3;(2)CH3CHCH2CCH;(3)C=C(4)CH3CCCH2CH2CCHHHBr4.解:NaNH2/液NH3(1)CH3CCHCH3CCNaH2HBrCH3CCHCH3CH=CH2CH3CH2CH2Br(两步合成,不可颠倒!)ROORLindlar催化剂H2CH3CCNaCH3CH2CH2BrCH3CH2CH2CCCH3CH3CH2CH2CH=CHCH3Lindlar催化剂BrH2HBr(2)CH3CCHCH3CH=CH2CH3CHCH3Lindlar催化剂=Br2HBr(3)CH3CCHCH3CCH3Br5.解:NaNH2/液NH3(1)HCCHHCCNaH2HBrHCCHCH2=CH2CH3CH2BrLindlar催化剂OHH2HOHCCNa2CH3CH2BrCH3CH2CCHCH3CH2CH=CH2CH3CH2CHCH3H3PO4Lindlar催化剂(1)B2H6(3)CH3CH2CH2CH2CH=CH2CH3CH2CH2CH2CH2CH2OH(2)H2O2/OH-6.解:CH3CH2CCHAgNO3/NH4OH(2)CH3CCCH3己烷1,3-己二烯Br2/CCl4(-)褪色褪色白色沉淀(-)(-)白色沉淀AgNO3/NH4OH(3)8.解:1-己炔OA.(CH3)2CHCCH;B.(CH3)2CHCCCH2CH2CH3;C.(CH3)2CHCOOH;D.CH3CH2CH2COOH;E.(CH3)2CHCCH3=各步反应式:CH3CH2CH2BrNa(CH3)2CHCCH(CH3)2CHCCH(CH3)2CHCCCH2CH2CH3(B)(A)KMnO4/H+(CH3)2CHCCCH2CH2CH3(CH3)2CHCOOH+CH3CH2CH2COOH(B)(C)(D)OHgSO/HSO424(CH3)2CHCCH+H2O(CH3)2CHCCH3(A)(E)第五章脂环烃2.解:(1)1,3-二甲基环己烯;(2)5,5-二甲基-1,3-环戊二烯;(4)7,7-二甲基双环[4.1.0]庚烷;(6)4-甲基-1-乙基螺[2.5]辛烷;(8)4-甲基-1-异丙基双环[3.1.0]己烷3.解:CH3(4)(6)CH3C2H55.解:(1)CH3CH2CH2CH3;CH3CHCH2CH2;CH3CH2CHCH3BrBrICH3(2)CH3CH3BrOOO==OHCCH2CH2CH2CH2CCH3O=COOH(3)+CO2(4)Br(5)HCNHCOOCH36.解:丙烷环丙烷丙烯Br2/CCl4(-)褪色褪色KMnO4溶液(-)褪色第6章有机化合物的波谱分析3.解:(B)>(A)>(C)。属于磁各向异性效应的影响。可参见表6-2。6.解:(1)CH3CCH2CH=OOCH3OCH3O(2)CH3CCH2CH2BrO(3)CH3CH2CCH2CH2Cl==(4)建议将“C3H6Cl2”修改为“C4H7Cl3”。为:ClClCH3CHCCH3Cl。第七章芳烃芳香性1.解:(1)反(或E)-2-苯基-2-丁烯;(3)1,5-二硝基萘;(5)2-甲基-4-溴苯胺;(6)4-羟基-5-溴-1,3-苯二磺酸;CH3HON(7)(10)C=C2NO2CH3CH2CHCH2CH3NO2HCH22.解:OHCH3HClNO2(1)NH2BrCOOHCOOHNO2(2)CH33.解:COOHCH3CH3CH3CH3NO2SO3H+NO2CH3SO3HNO2(1)(2);;+COOHNO2CH2CH3CH3CHBrCH3CH2Cl(3);(4)(5)O2NNO2BrCH3COCH2CH3NO2C(CH3)3C(CH3)3C(CH3)3COCH2CH3(6);;(7)CHO+HCHO;(8);CH2CH3COOHCH3COOHBrCOOH(9)(10)+NO2Br(-)Br2/CCl4褪色褪色Ag(NH3)2NO3(-)(白色)4.解:CH2CH3(1)CH=CH2CCH苯(3)甲苯苯乙炔KMnO4(-)褪色褪色Ag(NH3)2NO3或Cu(NH3)2Cl(-)Ag镜7.解:注意多步合成,不可颠倒!!!CH3(2)KMnO4COOHBr2/FeBrCOOHCH3(3)浓HNO3浓H2SO4CH3KMnO4NO2COOHNO28.解:注意多步合成,不可颠倒!!!(2)CH3CH2CH2COClAlCl3OCCH2CH2CH3Zn-Hg,HCl=CH2CH2CH2CH39.解:(4)(5)具有芳香性,(1)(2)(3)(6)无芳香性。第8章立体化学2.解:只有(3)、(4)、(5)是非手性分子,其余都是手性分子。须说明的是(3):CH3最稳定的结构为:CH3,有对称中心,非手性分子。(4)(5)则有对称面。6.解:先把题目的各个手性碳原子,进行RS标记,再进行画Fischer投影式:CH3H(1)BrBrCH3(2)HBrCHOCH3HC2H5(2S,3S)CH3(2R,3S)7.解:(1)对映体;(2)同一种物质;(3)对映体;(4)非对映体;(5)同一种物质;(6)同一种物质(有对称中心);(7)同一种物质(有对称中心);(8)对映体9.解:本题要进行修改!原文:旋光性物质A,分子式为C7H11Br。A和HBr反应产生异构体B和C,B有光学活性,C则没有光学活性。B用1mol的叔丁醇钾处理得到A,C用1mol的叔丁醇钾处理得到没有光学活性的混合物。A用1mol的叔丁醇钾处理得到D,D的分子式为C7H10。1molD经臭氧化,用Zn和水处理后,得到两分子的甲醛和一分子的1,3-环戊二酮。试推测A、B、C、D的立体结构式,并写出各步化学反应。将上述下画线文字内容删除。A、B、C、D的结构式为:BrCH3BrBrA、B、C、D、CHCH2Br2CH2CH3CH3BrCH3CH3各步化学反应式略。第9章卤代烃相转移催化反应邻基效应1.解:(2)(E)-3-溴-2-戊烯;(4)1-甲基-2-氯螺[2.3]-4-己烯;(6)1-氯甲基环己烷;(8)3-甲基-6-溴环己烯2.解:CH3(1)CH2=CHCH2Br;(2)CH2Cl;(3)CHCl3;(5)CH3CH2MgBr;(6)BrHC3H75.解:由易到难顺序:(2)BCA。CH3CH3(A)CH3CHCH=CH2;(B)CH3C=CHCH3;(C)CH3C=CHCH3CH3产物ABC分别为:同的。6.解:,其中(B)(C)的产物是相(1)CH3CHCH=CH2;CH2=CHCH=CH2;CH3CHCH=CH2+CH3CH=CHCH2;BrBrBrCH3CH3BrBr(2)CH3C=CHCH3;(3);(4)CHCH3;CHCH3;CH2BrCH2OHCH3ClCH3CH3CH3CH3(5)C2H6+CH3CCMgBr;(6);;;;CH2ClCH2ICH2CNCH2COOH(7)(CH3)2C=CH2;(8)CH3CH37.解:(1)反应机理一般认为属于SN1。活性顺序为:(a)C>A>B;(b)C>A>B。(2)反应机理一般认为属于SN2。活性顺序为:B>A>C。8.解:9.解:(1)B>C>A;(2)B>C>A。10.解:(1)B>A>C;(2)A>B>C;(3)D>C>B>A(参见离去基团的影响)。11.解:(1)A>C>D>B;(2)C>A>B。12.解:(2)氯化苄烯丙基氯Br2/CCl4(-)(褪色)CH3CH3-+OH(1)CH3CCHCH2CH3CH3CCHCH2CH3--BrCH3CH3CH3CH3OHCH3-甲基迁移++OHCH3CCHCH2CH3CH3CCHCH2CH3CH3CCHCH2CH3CH3CH3CH3Br++重排(2)CH3CHCH=CH2CH3CHCH=CH2CH3CH=CHCH2OH-OH-CH3CHCH=CH2CH3CH=CHCH2OHOH第10章醇酚醚1.解:(3)3-环己烯-1-醇;(3)(3Z)-4-甲基-3-己烯-1-醇;(4)1-苯基-1-丙醇;(8)8-羟基-2-萘磺酸2.解:(1)CH3OH;(2)CH2CHCH2;(3)CH3CH2CHCH3OHOHOHOHO2NNO2(4)(5)(6)NO2HCH2OHHO(7)C=C(8)HOHCH3OHOHOCH3CH3HHCH3O3.解:CH2CH2Cl(1)CH3CH2CH2OCH2CH2CH3;(2);(3)OHOH3CCH3CH3CH=CHCHOOOCCH3(7)CH3CCH2;(8)(CH3)2C=CH2+CH3OH(4)(CH3)2C=CH2;(5)(6)OCH3OHCH34.解:CH3(2)CH3CH3OHCH2OHOCH3FeCl3(紫色)(-)(-)Na(-)6.解:(C)﹥(D)﹥(A)﹥(B)7.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