有机化学答案(何建玲)

第二章烷烃1.写出庚烷的所有的构造异构体的结构式，并用系统命名法命名。2.写出下列化合物的结构式，并指出化合物分子中碳原子和氢原子的类型。CH3CH2CH2CH2CH2CH2CH3CH3CH2CH2CH2CHCH3CH3CH3CH2CH2CHCH2CH3CH3正庚烷2-甲基己烷3-甲基己烷CH3CH2CHCH(CH3)2CH3CH3CHCH2CHCH3CH3CH3(CH3)3CCH2CH2CH32，3-二甲基戊烷2，4-二甲基戊烷2，2-二甲基戊烷CH3CH2CCH2CH3CH3CH2CHCH2CH3(CH3)3CCH(CH3)2CH3CH3CH2CH33，3-二甲基戊烷3-乙基戊烷2，2，3-三甲基丁烷(CH3)2CHCCH2CH2CH2CH3CH3CH3CH3CHCHCH2CH3CH3CH2CH3CH3CHCH3CCHCH3CH2CH3CH3CH3CH3CH2CHCHCH2CH2CH2CH2CH3CH3CH2CH3(1)(2)(3)(4)CH3CHCH3CHCH2CH3CHCH3CH2CH2CH3CCH3CH3H3CCH3CH3CH2CH2CHCH2CH2CH2CH2CH3CH(CH3)2CH3CHCH2CH2CHCHCH2CH2CH2CH3CH3CH2CH3C(CH3)3CH3CHCH3CH2CCH3CHCH2CH3CH(CH3)2CH3CH3CH2CHCH2CHCH2CH2CH2CH3CH2CH3CHCH2CH3H3C(5)(6)(7)(8)(9)(10)3.用系统命名法命名下列各化合物。⑴4-异丙基辛烷⑵2,2,4-三甲基庚烷⑶2-甲基-3-乙基己烷⑷2,5-二甲基-4-乙基辛烷⑸3,5-二甲基-4-异丙基壬烷⑹3-甲基-4,6-二乙基壬烷⑺2,3-二甲基-5-乙基辛烷⑻2,5-二甲基-3-乙基庚烷4.以纽曼投影式，画出下列化合物的最稳定和最不稳定的构象式。⑴乙烷⑵1，2-二氯乙烷⑶丙烷⑷1-溴丙烷5.不查表，试给下列烃类化合物按沸点升高的次序排列。⑴2，4-二甲基戊烷⑵正庚烷⑶2，3-二甲基己烷⑷3-甲基戊烷⑸正己烷⑹3-甲基己烷解：烷烃类化合物的沸点高低遵循以下规律：随着化合物分子质量的增加（即随着化合物碳原子数的增多），沸点升高；同碳原子数的化合物，支链越多沸点越低；化合物的沸点由高到低的顺序：⑶⑵⑹⑴⑸⑷6.已知某化合物，其相对分子质量为86，写出符合下列条件的该化合物的结构式：⑴一氯代时，能生成五种一氯衍生物⑵一氯代时，能生成四种一氯衍生物⑶一氯代时，能生成三种一氯衍生物⑷一氯代时，能生成两种一氯衍生物解：CnH2n+2=86解得n=6故该化合物为六个碳的烷烃HHHHHHHHHHHHClHHClHHHClHClHHHHHCH3HHHHHCH3HHCH3HHBrHHHBrHCH3HH(1)(2)(3)(4)CH3CHCH2CH2CH3CH3CH3CH2CHCH2CH3CH3CH3CH2CH2CH2CH2CH3(CH3)3CCH2CH3(CH3)2CHCH(CH3)2(1)(2)(3)(4)或7.某烷烃相对分子质量为72，一元溴代产物只有一种，试推断此烷烃的结构式。解：CnH2n+2=72解得n=5故该化合物为五个碳的烷烃该烷烃的结构式为CH3CCH3CH3CH3第三章不饱和烃1.试写出分子式为C6H12的烯烃的所有可能的异构体，并用系统命名法命名解：2.写出下列化合物的结构式3.用系统命名法命名下列化合物⑴3，5-二甲基-2-庚烯⑵3-甲基-4-异丙基-3-庚烯⑶（E）-2-氯-3-碘-2-戊烯⑷（Z）-3-异丙基-2-己烯⑸反-2-氯-3-溴-2-丁烯⑹（2Z，4E）-3-甲基-2，4-庚二烯⑺5-甲基-3-乙基-1-己炔⑻4-甲基-2-己炔4.试写出异丁烯与下列各试剂反应的主要产物H2CCHCH2CH2CH2CH3CH3CHCHCH2CH2CH3CH3CH2CHCHCH2CH3H2CCCH3CH2CH2CH3(CH3)2CCHCH2CH3(CH3)2CHCHCHCH3(CH3)2CHCH2CHCH2H2CCHCHCH2CH3CH3CH3CHCCH2CH3CH3H2CCCH2CH3CH2CH3H2CCCH(CH3)2CH3(CH3)2CC(CH3)2H2CCHC(CH3)3(1)(2)(3)(4)CH3CCCH2CH2CH3CH3CH3CCH3CHCH(CH3)2CH3CCH3CH3CH2CCH2CH2CH2CH3CH2CH3CCH3CClCH3IH2CCCHCH3CH2CH3CH2CCCHCH2CH3CH3HCCCCHCH3CH3H2CCCHClCH2(5)(6)(7)(8)CH3CHCH3CH3(1)(2)CH2BrCBrCH3CH3CH3CBrCH3CH3(3)(4)CH2BrCHCH3CH3(5)(6)CH2BrCCH3OHCH3CH2CCH3OHCH3OH5.试写出甲基环己烯与下列各试剂反应的主要产物6.完成下列反应式7.用化学方法区别下列各组化合物⑴2-甲基丁烷(-)3-甲基-1-丁烯Br2/CCl4褪色Ag(NH3)2NO3(-)3-甲基-1-丁炔褪色白色沉淀⑵丁烷(-)1-丁炔KMnO4褪色Cu(NH3)2Cl砖红色沉淀2-丁烯褪色(-)(7)(8)(9)(10)COH3CCH3+CO2+H2O(CH3)2CHCH2OHCOH3CCH3+HCHOCH2C(CH3)2OCH3(1)(2)BrCH3(3)CH3Br(4)CH3Br(5)CH3BrOH(6)CH3OHOHBr(7)COH3CCH2CH2CH2CH2COOH(8)CH3OH(9)(10)COH3CCH2CH2CH2CH2CHOCH3O(1)(2)CH3CHCHCH3CH3CHCHCH3BrBrH2CCHCHCH2CH3CH2CCAg(3)CH3CH2CCCu(4)CH3CH2CCH2OH[]COH3CCH2CH3(5)COOCH3(6)[]CH2CCHClCH2n(7)(8)CH3CHCHBrCH2CH3CHCHCH2Br+BrBrCOOCH3⑶丁烷(-)1-丁炔Br2/CCl4褪色白色沉淀1-丁烯褪色Ag(NH3)2NO3(-)顺丁烯二酸酐(-)1，3-丁二烯褪色(-)白色沉淀8.合成题(1)CH3CHBrCH3CH3CH2CH2BrCH3CHBrCH3KOH/醇CH3CHCH2HBr/ROORCH3CH2CH2Br(2)CH3CHCH3OHCH3CH2CH2OHCH3CHCH3OHH2SO4△CH3CHCH2B2H6H2O2/NaOHCH3CH2CH2OHCH3CH2CH2OHCH2CHCH3ClCl(3)CH3CH2CH2OHH2SO4△CH3CHCH2Cl2CH2CHCH3ClClH2CCHCH3CH2CHCH2ClBrBr(4)H2CCHCH3Cl2500℃H2CCHCH2ClBr2/CCl4CH2CHCH2ClBrBrH2CCHCH3CH2CHClCH2O(5)H2CCHCH3Cl2500℃H2CCHCH2ClCH3COOOHCH2CHClCH2O(6)HCCCH3CH3CH2CH2CH2CH2CH3NaCCCH3HCCCH3NaHCCCH3H2/LindlarCH3CHCH2HBr/ROORCH3CH2CH2BrNaCCCH3CH3CH2CH2Br+CH3CCCH2CH2CH3H2/NiCH3CH2CH2CH2CH2CH3(7)HCCCH3ONaCCCH3HCCCH3NaHCCCH3H2/LindlarCH3CHCH2HBr/ROORCH3CH2CH2BrNaCCCH3CH3CH2CH2Br+CH3CCCH2CH2CH3+H2OH2SO4HgSO4O9.以四个碳原子及以下的烃为原料合成下列化合物(8)HCCHCH3CH2CH2CH2OHNaCCHNaHCCHHCCHH2/LindlarH2CCH2+HBrCH3CH2BrCH3CH2BrNaCCH+CH3CH2CCHH2/LindlarCH3CH2CHCH2B2H6H2O2/NaOHCH3CH2CH2CH2OHNaCCHNaHCCH(1)OH2CCHCH2Cl+△CH2ClH2CCHCH2ClH2CCHCH3Cl2500℃CH2Cl+CH2CCHCNaHC+H2OH2SO4HgSO4O(2)BrBrCNH2CCHCH3+NH3+O2磷钼酸铋H2CCHCNH2CCHCN+△CN+Br2BrBrCN(3)CH2ClH2CCHCH2Cl+△CH2ClH2CCHCH2ClH2CCHCH3Cl2500℃H2/NiCH2Cl10.试分析，乙烯在溴的氯化钠水溶液中进行反应，会生成哪几种产物，为什么？解：乙烯与溴先反应生成环状的溴翁碳正离子，后与溶液中的负离子反应，溶液中含有的负离子有Br-、Cl-、OH-等，故反应生成以下三种产物。11.烯烃A和B的分子式相同，都是C6H12，经酸性高锰酸钾氧化后，A只生成酮，B的产物中一个是酮，另一个是羧酸，试推测A和B的结构。解：12.有A、B、C三个化合物，其分子式相同，都为C5H8，它们都能使溴的四氯化碳溶液褪色，A与硝酸银的氨溶液作用生成沉淀，而B、C不能，当用热的高锰酸钾氧化时，A可得到正丁酸和二氧化碳，B可得到乙酸和丙酸，C得到戊二酸。试推断A、B、C的结构式。解：13.分子式为C8H12的化合物A，在催化加氢作用下生成4-甲基庚烷，A经林德拉催化加氢得到B，B的分子式为C8H14，A在液态氨中与金属钠作用得到C，C的分子式也为C8H14，试写出A、B、C的结构式。A的结构是否唯一？试写出所有可能的A的结构式。解：Ａ的结构不唯一．H2CCH2+Br2+NaCl+H2OCH2CH2BrBrCH2CH2BrClCH2CH2BrOH++ABCCHH3CH3CCCH3CCH3CH3H3CCH2CH3CCH3CCH3CH3H3CKMnO4/H+COH3CCH3CCHH3CH3CCH2CH3KMnO4/H+COH3CCH3+CH3CH2COOHABCH3CH2CH2CCHCH3CCCH2CH3CCH3CH2CH2CCHBr2/CCl4CH3CH2CH2CCHCH3CH2CH2CBr2CHBr2Ag(NH3)2NO3CH3CH2CH2CCAg(白)CH3CH2CH2CCHKMnO4/H+CH3CH2CH2COOH+CO2KMnO4/H+KMnO4/H+CH3CCCH2CH3CH3COOH+CH3CH2COOHHOOCCH2CH2CH2COOHABCCH3CCCCH2CH2CH2CH3CCH3CHCHCH2CH2CH2CH3CCHHCH3CCH2CH2CH2CH314.有三种分子式为C5H10的烯烃A、B、C，它们为同分异构体，催化加氢后均生成2-甲基丁烷。A和B经酸催化水合都生成同一种叔醇；B和C经硼氢化-氧化得到不同的伯醇。试推测A、B、C的结构。解：15.某开链烃A，分子式为C7H10，A经催化加氢可生成3-乙基戊烷，A与硝酸银的氨溶液作用产生白色沉淀，A在Pd/BaSO4作用下吸收1molH2生成化合物B，B可与顺丁烯二酸酐作用生成化合物C。试推测化合物A、B、C的结构。解：ABCCH3CCCCHCH2CH3CH3CCH3CHCHCHCH2CH3CH3CCHHCH3CCHCH2CH3CH3ABCCH3CCCHCCH3CHCHHCH3CHCHCH3CHCH3CHCH3CCHHCHH3CCHCH3CHCH3ABCCH3CCCHCCH3CHCHHCH2CHCH3CH3CH2CHCH2CH2CCHHCHH3CCH2CHCH3CH2ABCCH3CCHCH3CH3H2CCCH2CH3CH3H2CCHCHCH3CH3CH3CCHCH3CH3H2CCCH2CH3CH3H2CCHCHCH3CH3H2/NiH2/NiH2/NiCH3CHCH2CH3CH3CH3CHCH2CH3CH3CH3CHCH2CH3CH3CH3CCHCH3CH3+H2OH++H2OH+H2CCCH2CH3CH3CH3CCH2CH3CH3OHH2CCCH2CH3CH3H2CCH