有机化学汪小兰第四版课后习题答案118章.docx

1、有机化学汪小兰第四版课后习题答案118章1.1第一章 绪论离子键化合物共价键化合物熔沸点高低溶解度溶于强极性溶剂溶于弱或非极性溶剂硬度高低1.2 NaCl 与 KBr 各 1mol 与 NaBr 及 KCl 各 1mol 溶于水中所得溶液相同。因为两者溶液中均为 Na+ , K+ , Br, Cl离子各 1mol。由于 CH4 与 CCl4 及 CHCl3 与 CH3Cl 在水中是以分子状态存在，所以是两组不同 的混合物。1.3C +6 2 4 H +1 1y y yC 1s 2s 2p 2p 2p yH x zz2pxxz2pyx xz2pz2sCH4 中 C 中有4个电子与氢成键为 SP3

2、 杂化轨道,正四面体结构H1.4CH4 SP3 杂化C H HHHa. HC C H或 H C C Hb. c.H NH C ClH d. H S HH H H H HO O OHO H He. H O Nf. g. H O PO H 或H O P O Hh. H C C HO H C HO O H HH HO O1.5i. H C C H j.ClH O S O H 或OHH O S O H Ob. c. H Br d. e.C C O f. O H ClClClH ClH3CH H3CCH31.6 电负性 O S , H2O 与 H2S 相比，H2O 有较强的偶极作用及氢键。第二章 饱和脂

3、肪烃2.1 a. 2,4,4三甲基正丁基壬烷 butyl2,4,4trimethylnonane b. 正 己 烷 hexane c. 3,3二乙基戊烷 3,3diethylpentane d. 3甲基异丙基辛烷 isopropyl3methyloctane e. 甲基丙烷（异丁烷） methylpropane (iso-butane) f. 2,2二甲基丙烷（新戊烷）2,2dimethylpropane (neopentane) g. 3甲基戊烷 methylpentane h. 甲基乙基庚 烷 5ethyl2methylheptane2.2 a = b = d = e 为 2,3,5三甲基

4、己烷 c = f 为 2,3,4,5四甲基己烷2.3a. 错，应为 2,2二甲基丁烷Cb. c.d. e. f. 错，应为 2,3,3三甲基戊烷g. 错，应为 2,3,5三甲基庚烷 h.2.5 c b e a d2.6Cl Cl3 种 1 2 32.7 a 是共同的2.8BrBr BrClBrH BrCH BrA BH HD H H2.10H H H H H HH H H H Br Br这个化合物为2.11 稳定性 c a b第三章 不饱和脂肪烃3.1 用系统命名法命名下列化合物a. 2乙基丁烯 ethyl1butene b. 2丙基己烯 propyl1hexene c. 3,5二甲基庚烯 3

5、,5dimethyl3heptene d. 2,5二甲基己烯 2,5dimethyl2hexene3.2a. b. 错，应为1丁烯 c. d. e. f. 错，应为2,3二甲基戊烯 g.h. 错，应为2甲基3乙基己烯3.4 下列烯烃哪个有顺、反异构？写出顺、反异构体的构型，并命名。答案： c , d , e ,f 有顺反异构c. C2H5CHCH2I CHHCC2H5CH2I d.CHH3CC HCH(CH3)2CHH3CCHH CCH(CH3)2( Z )1碘2戊烯 ( E )1碘2戊烯( Z )4甲基2戊烯H( E )4甲基2戊烯He. H HH3C Hf. C C C HC H3CC C

6、 CH2C C CH HCH2H3C 2 5C CH( Z )1,3戊二烯( E )1,3戊二烯H H( 2Z,4Z )2,4庚二烯H HC C H H3C C CH3C HC C H C CC2H5H3C HC C H H C CH C2H5( 2Z,4E )2,4庚二烯H H( 2E,4Z )2,4庚二烯H C2H5( 2E,4E )2,4庚二烯3.5 完成下列反应式，写出产物或所需试剂a. CH3CH2CH=CH2 H2SO4 CH3CH2CH CH3OSO2OHHBr (CH3)2C-CH2CH3b. (CH3)2C=CHCH3c. CH3CH2CH=CH21). BH32).H2O2

7、 , OHBrCH3CH2CH2CH2OHH2O / H+ CH CH CH-CHd. CH3CH2CH=CH21). O33 2 3OHe. (CH3)2C=CHCH2CH32). Zn , H2OCH3COCH3 + CH3CH2CHOf. CH2=CHCH2OH Cl2 / H2O ClCH2CH-CH2OH OH3.63.71己烯 正己烷Br2 / CCl4or KMnO4无反应 褪色正己烷1己烯CH3CH=CHCH3 CH2=CHCH2CH3或3.8 将下列碳正离子按稳定性由大至小排列：CH3CH3 CH3CH3 + +H3C CCH CH3 H3C CCH CH3 H3C CCH2

8、 CH2+3.9 写出下列反应的转化过程：CH3CH3H3CH3CC=CHCH2CH2CH2CH=CCH3 H+CH3H3CH3C+C-CH2CH2CH2CH2CH=CCH3CH33.10+ _ H+Hor3.11 a. 4甲基己炔 methyl2hexyne b. 2,2,7,7四甲基3,5辛二炔 2,2,7,7tetramethyl3,5octadiynec.3.13a. HC CH + Hd.LindlarCH C H2C CH2 b. HC CH Ni / H2 CH CH2catH2SO43 3HgCl2c. HC CH + H2OHgSO4CH3CHO d. HC CH + HCl

9、BrCH2=CHCle. H3CC CHHgBr2HBrCH3C=CH2BrHBrCH3-C BrCH3f. H3CC CH + Br2 CH3C=CHBrBrg. H3CC CH + H2OH2SO4HgSO4CH3COCH3h. H3CC CH + HBr HgBr2 CH3C=CH2BrLindlarHBri.3.14H3CC CH + H2catCH3CH=CH2(CH3)2CHBra. 正庚烷1,4庚二烯1庚炔+Ag(NH3)2灰白色无反应1庚炔正庚烷1,4庚二烯Br2 / CCl4褪色 无反应1,4庚二烯 正庚烷b. 2甲基戊烷2己炔1己炔3.15+Ag(NH3)2灰白色无反应1己

10、炔2甲基戊烷2己炔Br2 / CCl4褪色 无反应2己炔2甲基戊烷3 2 2a. CH CH CH C CHHClCl(过量) CH3CH2CH2C ClCH3H+b. CH3CH2C CCH3 + KMnO4CH3CH2COOH + CH3COOHc. CH CH C CCH+ H OH2SO43 2 32HgSO4CH3CH2CH2COCH3 + CH3CH2COCH2CH3d. CH2=CHCH=CH2 + CH2=CHCHO CHOe. CH3CH2C CH + HCN CH3CH2C=CH2CN3.16CH3CHCH2C CH H3C3.17 A H3CCH2CH2CH2C CH B

11、 CH3CH=CHCH=CHCH33.183 2CH2=CHCH=CH2HBr CH CH CH=CH Br+ CH3CH=CHCH2BrCH2=CHCH=CH22HBr CH3CH CHCH3+ CH3CH CH2CH2Br BrBr BrCH2=CHCH2CH=CH23 2 2HBr CH CH CH CH=CH BrCH2=CHCH2CH=CH22HBrCH3CH BrCH2 CHBrCH34.1 C5H10 不饱和度=1第四章 环烃a. 环戊烷b. 1甲基环丁烷cyclopentane1methylcyclobutanec. 顺1,2二甲基环丙烷cis1,2dimethylcyclop

12、ropaned.反1,2二甲基环丙烷trans1,2dimethyllcyclopropanee. 1,1二甲基环丙烷1,1dimethylcyclopropanef. 乙基环丙烷 ethylcyclopropane4.3 a. 1,1二氯环庚烷 1,1dichlorocycloheptane b. 2,6二甲基萘 2,6dimethylnaphthalene c. 1甲基异丙基1,4环己二烯 1isopropyl4methyl1,4cyclohexadiene d. 对异丙基甲苯 pisopropyltoluene e. 氯苯磺酸 chlorobenzenesulfonic acidCH3C

13、lf. 2chloro4nitrotoluene g.NO22,3dimethyl1phenyl1penteneCH3 CH3h.cis1,3dimethylcyclopentane4.4 完成下列反应：CH3CH3a. HBr Brb. + Cl2c. + Cl2CH2CH3高温 ClCl+Cl ClClBrC2H5d. + Br2 FeBr3 BrC2H5 +e. CH(CH3)2+ Cl2Cl高温 C(CH3)2CH3 O O3f.Znpowder , H2O CHOCH3g.H2SO4H2O ,CH3OHh. + CH2Cl2CH3AlCl3 CH2CH3CH3NO2i. + HNO3

14、 +NO2+j. + KMnO4 H COOHk.4.5CH=CH2+ Cl2CH CH2ClCl1. 24.6CH3CH3CH3+ Br2FeBr3CH3BrCH3CH3+CH3CH3CH3BrCH3+ Br2FeBr3+ CH3BrBrCH3CH3+ Br2FeBr3CH3BrCH34.7 b , d 有芳香性4.8CH3a. AB1,3环己二烯苯2Ag(NH3) +灰白色C无反应BC 1己炔无反应 ABBr2 / CCl4褪色Ab. A B环丙烷丙烯KMnO4无反应A褪色B4.9Cl COOH NHCOCH3a. b. c.CH3COCH3 OCH3d. e. f.NO24.10a. B

15、r2FeBr3Br HNO3 BrH2SO4NO2b. HNO3H2SO4NO2Br2FeBr3BrO2NCH3c.CH3d.2 Cl2FeCl3+ Cl2CH3ClClFeCl3CH3ClKMnO4COOHClCH3e.KMnO4COOHCl2FeCl3COOH ClCH3f.HNO3H2SO4H3CNO2Br2Br2FeBr 3CH3BrNO2CH3 CH3g. Br2KMnO4COOHHNO3COOH4.11FeBr3BrH2SO4BrNO2Br可能为 or or or oror or 4.12即环辛烯及环烯双键碳上含非支链取代基的分子式为 C8H14O2 的各种异构体，例如以上各种异构

16、体。H3C C2H54.13A. Br Br4.14Br Br Br BrCl BrA. B C DBrCl Cl Cl4.15 将下列结构改写为键线式。a. b. c. orOOd. O e. H5.4第五章 旋光异构a. CH2 CH2CH2CH3OH BrCH2OH H BrCH2CH3( R )CH2OH Br HCH2CH3( S )b. HOOCCH CHCOOHCOOHH BrCOOH H BrCOOH Br HBr BrH BrCOOH ( meso- )Br H COOH( 2S,3S )H BrCOOH( 2R,3R )c. H3CCH BrCH COOH BrCOOH H

17、 Br H BrCH3COOH Br H Br HCOOHCOOH H BrBr HCOOHCOOH Br HH BrCH3( 2S,3R ) ( 2R,3S ) ( 2S,3S ) ( 2R,3R )d. CH3C=CHCOOH CH35.6( 无 )5.7C5H10O2COOH H CH3CH2CH3( R )COOH H3C HCH2CH3( S )C6H12 =1*5.10A CH2=CHCHCH2CH3CH3B CH3CH2CHCH2CH3CH3( I )COOH H OHCH3( R )纸面上旋转 90 oOH HOOC CH3H( S ) COOH( 对映异构 )离开纸面旋转HO

18、 H CH3( S )( 对映异构 )第六章 卤代烃6.1BrCH3Br Cla. CH3CH-CHCH3CH3b. H3CC CH3CH2I c.d. Cl Cl e.f. 2碘丙烷 iodopropane g. 三氯甲烷 trichloromethane or Chloroformh. 1,2二氯乙烷 1,2dichloroethane i. 氯丙烯 chloro1propene j. 1氯丙烯 chloro1propene6.4 写出下列反应的主要产物，或必要溶剂或试剂Mg CO2 H+C H CH COOMgClC H CH COOHa. C6H5CH2ClEt2OC6H5CH2MgC

19、l6 5 2H2O6 5 2b. CH2=CHCH2Br + NaOC 2H5 CH2=CHCH2OC2H5CH=CHBrc. CH2Br+ AgNO3EtOHr.tCH=CHBrCH2ONO2+ AgBrBr光照 CH2=CHCHO CHOd. + Br2 KOH-EtOHCH2Cl e.ClNaOH H2OBrBrCH2OHClf. CH3CH2CH2CH2Br MgCH CH CH CH MgBr C2H5OHEt2Og.3 2 2 2 OHCH3CH2CH2CH3 + BrMgOC2H5CH3 ClCH3h.+ H2O OHSN2 历程CH3CH3OH CH3+ H2O OH+SN1

20、历程Cl OHBri. KOH-EtOHj. CH2=CHCH2Cl CNCH2=CHCH2CNk. (CH3)3Cl + NaOH H2O (CH3)3COH6.5 下列各对化合物按 SN2 历程进行反应,哪一个反应速率较快?a. (CH3)2CHI (CH3)3CCl b. (CH3)2CHI (CH3)2CHClc. CH2Cl Cl d. CH3CHCH2CH2Br CH3CH3CH2CHCH2BrCH3e. CH3CH2CH2CH2Cl CH3CH2CH=CHCl6.6 将下列化合物按 SN1 历程反应的活性由大到小排列 b c a6.7 (a) 反应活化能 (b) 反应过渡态 (c

21、) 反应热 放热6.8A CH3CH2CHCH3BrB CH2=CHCH2CH3 C. CH3CH=CHCH3 (Z) and (E)6.9 怎样鉴别下列各组化合物？鉴别 a , b , d AgNO3 / EtOH c. Br26.10CH3CH3CHCH2BrCH3CH3KOH-EtOH CH3C=CH2CH3 a. HBrCH3H+H2O CH3 C OHb.CH3CH3CH3 C BrCH2BrCH3 C BrCH3CH3C CH2OH Brd. c. e.6.11 A BrCH2CH2CH3 B. CH2=CHCH3 C. CH3CHBrCH37.1 命名下列化合物第七章 醇 酚 醚a. (3Z)戊烯醇 (3Z)penten1ol b. 2溴丙醇 2bromopropanol c. 2,5庚二醇 2,5heptanediol d. 4苯基2戊醇 4phenyl2pentanole. (1R,2R) 2 甲基环己醇 (1R,2R) 2 methylcyclohexanol f.