有机化学汪小兰第四版课后习题答案(一至十八章).doc

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1、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1.2NaCl 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 杂化轨道,正四面体结构H1.4CH4 SP

2、3 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.HBrd.e.CCOf.O HClClClHClH3CHH3CCH31.6电负性 O S , H2O 与 H2S 相比，H2O 有较强的偶极作用及氢键。第二章饱和脂肪烃2.1a.2,4,4三甲基正丁基壬烷butyl2,4,4trimet

3、hylnonaneb. 正 己 烷hexanec.3,3二乙基戊烷3,3diethylpentaned.3甲基异丙基辛烷isopropyl3methyloctanee. 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methylpentaneh.甲基乙基庚 烷5ethyl2methylheptane2.2a = b = d = e为 2,3,5三甲基己烷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,

4、3,3三甲基戊烷g. 错，应为 2,3,5三甲基庚烷 h.2.5c b e a d2.6Cl Cl3 种 1 2 32.7a 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用系统命名法命名以下化合物a.2乙基丁烯ethyl1buteneb.2丙基己烯propyl1hexenec.3,5二甲基庚烯3,5dimethyl3heptene d.2,5二甲基己烯2,5dimethyl2hexene3.2a. b. 错，应为1丁烯 c. d. e. f. 错，

5、应为2,3二甲基戊烯 g.h. 错，应为2甲基3乙基己烯3.4以下烯烃哪个有顺、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 CH2CC 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 CCH

6、3C HCC H C CC2H5H3C HC C H H CCH 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完成以下反响式，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 , OHBrCH3CH2CH2CH2OHH2O / H+ CH CH CH-CHd. CH3CH2CH=CH21). O3323OHe. (CH3)2C=CHCH2CH3

7、2). Zn , H2OCH3COCH3 + CH3CH2CHOf. CH2=CHCH2OH Cl2 / H2O ClCH2CH-CH2OH OH3.63.71己烯 正己烷Br2 / CCl4or KMnO4无反响 褪色正己烷1己烯CH3CH=CHCH3 CH2=CHCH2CH3或3.8将以下碳正离子按稳定性由大至小排列：CH3CH3 CH3CH3 + +H3C CCH CH3 H3C CCH CH3 H3C CCH2 CH2+3.9写出以下反响的转化过程：CH3CH3H3CH3CC=CHCH2CH2CH2CH=CCH3 H+CH3H3CH3C+C-CH2CH2CH2CH2CH=CCH3CH3

8、3.10+ _ H+Hor3.11a.4甲基己炔methyl2hexyneb.2,2,7,7四甲基3,5辛二炔2,2,7,7tetramethyl3,5octadiynec.3.13a. HC CH + Hd.LindlarCHC H2C CH2 b. HC CH Ni / H2 CH CH2catH2SO433HgCl2c. HC CH + H2OHgSO4CH3CHO d. HC CH + HClBrCH2=CHCle. H3CC CHHgBr2HBrCH3C=CH2BrHBrCH3-C BrCH3f. H3CC CH + Br2 CH3C=CHBrBrg. H3CC CH + H2OH2

9、SO4HgSO4CH3COCH3h. 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灰白色无反响1庚炔正庚烷1,4庚二烯Br2 / CCl4褪色 无反响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灰白色无反响1己炔2甲基戊烷2己炔Br2 / CCl4褪色 无反响2己炔2甲基戊烷3 2 2a. CH CH CH C CHHClCl(过量) CH3CH2CH2C ClCH3H+b. CH3CH2C CCH3

10、+ KMnO4CH3CH2COOH + CH3COOHc. CH CH C CCH+ H OH2SO43232HgSO4CH3CH2CH2COCH3 + CH3CH2COCH2CH3d. CH2=CHCH=CH2 + CH2=CHCHO CHOe. CH3CH2C CH + HCN CH3CH2C=CH2CN3.16CH3CHCH2C CH H3C3.17A H3CCH2CH2CH2C CH B CH3CH=CHCH=CHCH33.1832CH2=CHCH=CH2HBr CH CH CH=CH Br+ CH3CH=CHCH2BrCH2=CHCH=CH22HBr CH3CH CHCH3+ CH3

11、CH CH2CH2BrBrBr BrCH2=CHCH2CH=CH2322HBr CH CH CH CH=CH BrCH2=CHCH2CH=CH22HBrCH3CH BrCH2 CHBrCH34.1C5H10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cis1,2dimethylcyclopropaned.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 ethylcyclopropane

12、4.3a.1,1二氯环庚烷1,1dichlorocycloheptaneb.2,6二甲基萘2,6dimethylnaphthalenec.1甲基异丙基1,4环己二烯1isopropyl4methyl1,4cyclohexadiened.对异丙基甲苯pisopropyltoluenee.氯苯磺酸chlorobenzenesulfonic acidCH3Clf. 2chloro4nitrotoluene g.NO22,3dimethyl1phenyl1penteneCH3 CH3h.cis1,3dimethylcyclopentane4.4完成以下反响：CH3CH3a. HBr Brb. + Cl

13、2c. + Cl2CH2CH3高温 ClCl+ClClClBrC2H5d. + Br2 FeBr3 BrC2H5 +e. CH(CH3)2+ Cl2Cl高温 C(CH3)2CH3 O O3f.Znpowder , H2O CHOCH3g.H2SO4H2O ,CH3OHh. + CH2Cl2CH3AlCl3 CH2CH3CH3NO2i. + HNO3 +NO2+j. + KMnO4 H COOHk.4.5CH=CH2+ Cl2CH CH2ClCl1. 24.6CH3CH3CH3+ Br2FeBr3CH3BrCH3CH3+CH3CH3CH3BrCH3+ Br2FeBr3+ CH3BrBrCH3CH

14、3+ Br2FeBr3CH3BrCH34.7b , d 有芳香性4.8CH3a. AB1,3环己二烯苯2Ag(NH3) +灰白色C无反响BC 1己炔无反响 ABBr2 / CCl4褪色Ab. A B环丙烷丙烯KMnO4无反响A褪色B4.9Cl COOH NHCOCH3a. b. c.CH3COCH3 OCH3d. e. f.NO24.10a. Br2FeBr3Br HNO3 BrH2SO4NO2b. HNO3H2SO4NO2Br2FeBr3BrO2NCH3c.CH3d.2 Cl2FeCl3+ Cl2CH3ClClFeCl3CH3ClKMnO4COOHClCH3e.KMnO4COOHCl2FeC

15、l3COOH ClCH3f.HNO3H2SO4H3CNO2Br2Br2FeBr 3CH3BrNO2CH3 CH3g. Br2KMnO4COOHHNO3COOH4.11FeBr3BrH2SO4BrNO2Br可能为orororororor 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，例如以上各种异构体。H3C C2H54.13A. Br Br4.14Br Br Br BrCl BrA. B C DBrCl Cl Cl4.15将以下结构改写为键线式。a. b. c. orOOd.Oe.H5.4第五章旋光异构a. CH2 CH2CH2CH3OH BrCH2OH

16、 H BrCH2CH3( R )CH2OH Br HCH2CH3( S )b. HOOCCH CHCOOHCOOHH BrCOOH H BrCOOH Br HBrBrH BrCOOH ( meso- )Br H COOH( 2S,3S )H BrCOOH( 2R,3R )c. H3CCH BrCH COOH BrCOOH H 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 )5.7C5H10O2

17、COOH 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 H CH3( S )( 对映异构 )第六章卤代烃6.1BrCH3BrCla. CH3CH-CHCH3CH3b. H3CC CH3CH2Ic.d. ClCle.f.2碘丙烷iodopropaneg.三氯甲烷trichloromethane or Chloroformh.1,

18、2二氯乙烷1,2dichloroethanei.氯丙烯chloro1propenej.1氯丙烯chloro1propene6.4写出以下反响的主要产物，或必要溶剂或试剂Mg CO2 H+C H CH COOMgClC H CH COOHa. C6H5CH2ClEt2OC6H5CH2MgCl6 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 H2O

19、BrBrCH2OHClf. CH3CH2CH2CH2Br MgCH CH CH CH MgBr C2H5OHEt2Og.3 2 2 2 OHCH3CH2CH2CH3 + BrMgOC2H5CH3ClCH3h.+ H2O OHSN2 历程CH3CH3OH CH3+ H2O OH+SN1 历程ClOHBri.KOH-EtOHj.CH2=CHCH2ClCNCH2=CHCH2CNk.(CH3)3Cl+ NaOHH2O(CH3)3COH6.5以下各对化合物按 SN2 历程进行反响,哪一个反响速率较快?a. (CH3)2CHI (CH3)3CCl b. (CH3)2CHI (CH3)2CHClc. CH2

20、Cl Cl d. CH3CHCH2CH2Br CH3CH3CH2CHCH2BrCH3e. CH3CH2CH2CH2Cl CH3CH2CH=CHCl6.6将以下化合物按 SN1 历程反响的活性由大到小排列b c a6.7(a)反响活化能(b)反响过渡态(c)反响热放热6.8A CH3CH2CHCH3BrB CH2=CHCH2CH3 C. CH3CH=CHCH3 (Z) and (E)6.9怎样鉴别以下各组化合物？鉴别a , b , dAgNO3 / EtOH c. Br26.10CH3CH3CHCH2BrCH3CH3KOH-EtOH CH3C=CH2CH3 a. HBrCH3H+H2O CH3

21、C OHb.CH3CH3CH3 C BrCH2BrCH3 C BrCH3CH3C CH2OH Brd. c. e.6.11ABrCH2CH2CH3 B.CH2=CHCH3 C.CH3CHBrCH37.1命名以下化合物第七章醇酚醚a. (3Z)戊烯醇(3Z)penten1olb. 2溴丙醇2bromopropanol c. 2,5庚二醇2,5heptanediold. 4苯基2戊醇4phenyl2pentanole. (1R,2R) 2 甲基环己醇(1R,2R) 2 methylcyclohexanolf. 乙二醇二甲醚 ethanediol 1,2 dimethyl etherg.(S) 环氧

22、丙烷(S) 1,2 epoxypropaneh. 间甲基苯酚mmethylphenoli.1苯基乙醇1phenylethanolj. 4硝基1萘酚4nitro1naphthol7.3完成以下转化OHOa.CrO3.Py2b.CH3CH2CH2OH浓 H2SO4 CH3CH=CH2Br2CH3CH-CH23Br BrKOH / EtOH CH C CHc.ACH3CH2CH2OH H+CH3CH=CH2NaHBr(CH3)2CHBr CH3CH2CH2OCH(CH3)2BrCH3CHCH3B.CH3CH2CH2OH H+CH3CH=CH2HBrHOH H+CH3CH2CH2BrOHNaCH3CH

23、CH3ONaCH3CHCH3CH3CH2CH2BrT.MOHd.CH3CH2CH2CH2OHHBr CH3CH2CH2CH2BrCH3CH2OHCH3CH2CH=CH2HOHCH CH CHCHOHOHe.浓 H2SO4NaOHH+ 3 2 3SO3H2f.CH2=CH2 稀 冷 KMnO4CH -CHOHOCH CH OCH CH OCH CH OH2 2 2 2 2 2 2 2H2O+Cl2ClCH2CH2OHOH OHClCH2CH2OH HOCH2CH2OCH2CH2OCH2CH2OHNaOHg.CH3CH2CH=CH21) B2H6 , Et2O2) H2O2 , OHCH3CH2C

24、H2CH2OHh.ClCH2CH2CH2CH2OHNaOHO7.5以下化合物是否可形成分子内氢键？写出带有分子内氢健的结构式。a , b , d 可以形成Oa,NO HOb.H3CH2CCH3OOHcis NOOO Htransd.O OHHO OHNNOOOO7.6写出以下反响的历程OH H+OH2aa_ H2O +bb+_ H+ _ H+H7.7写出以下反响的产物或反响物a. (CH3)2CHCH2CH2OH + HBr (CH3)2CHCH2CH2Brb. OH + HCl 无水 ZnCl2 ClOCH3c.+ HI (过量)+ CH3CH2CH2OCH3d. + HI (过量) O C

25、H3CH2CH2 e. (CH3)2CHBr + NaOC2H5 (CH3)2CHOC2H5 + CH3CH=CH2f. CH3(CH2)3CHCH3 KMnO4CH3(CH2)3CCH3OH OH Og. CH3CCH CH2CH3 HIO4 CH COOH + CH CH CHOO OH332CH3h. OHHIO4 CH COCH CH CHOOH 322OH OHi. + Br2Br BrCCl4 , CS2 中单取代CH3j. CH3(CH2)2CHCH2CH3 浓CH3H2SO4 CH CH CH=CHCH CH+ CH CH CH CH=CHCH7.832OH 分子内脱水2332

26、23AOCH3B.OHC. CH3I第八章醛、酮、醌3pentanonef.间甲氧基苯甲醛mmethoxybenzaldehydeg.甲基丁烯醛 3methyl2butenalh. BrCH2CH2CHOO8.1 a.异丁醛甲基丙醛methylpropanal isobutanal b.苯乙醛 phenylethanalc.对甲基苯甲醛pmethylbenzaldehyded.3甲基 丁酮methylbutanonee.2,4二甲基戊酮2,4dimethyli. Oj. CCl3CH2COCH2CH3 k. (CH3)2CCHO l. CH3CH2COCH2CHOm. CH=CHCHO n.

27、C CH3Oo. 丙烯醛 propenalp. 二苯甲酮 diphenyl Ketone8.3写出以下反响的主要产物OH Na.CH3COCH2CH3+H2NOHCH3CCH2CH3OHb.Cl3CCHO+H2OCl3CCHOHH+c.H3CCHO+KMnO4HOOCCOOHOHd.CH3CH2CHO稀 NaOHCH3CH2CH-CHCHO CH3CH3 H+CH3e.C6H5COCH3 + C6H5MgBrC6H5COMgBrH2OC6H5C OHC6H5f.O +H2NNHC6H5 NNHC6H5C6H5g.(CH3)3CCHO浓 NaOH(CH3)3CCH2OH+ (CH3)3CCOOH

28、 Oh.O+ (CH3)2C(CH2OH)2 无水 HClOi.O+K2Cr2O7 HHOOC(CH2)3COOHj. CHOKMnO4 COOH室温Ok.COCH3Cl2 , H2O OH+COOH + CHCl3Ol.CCH3 + Cl2HC CH2ClClClOHm.CH2=CHCH2CH2COCH3+ HClCH3-CHCH2CH2COCH3+CH3n.CH2=CHCOCH3+ HBrBrCH2CH2COCH3OHo.CH2=CHCHO+ HCNNCCH2CH2CHO+CH2=CHCHOCN8.4p.C6H5CHO+CH3COCH3稀 NaOHC6H5CHCH2C-CH3OHa. A

29、丙醛 B 丙酮 C 丙醇D 异丙醇2,4二硝基苯肼有沉淀无沉淀 Tollen 试剂 I2 / NaOH沉淀 无沉淀 无沉淀 黄色沉淀b. A 戊醛B 2戊酮C 环戊酮8.4完成以下转化Tollen 试剂沉淀 A无沉淀 B CI2 / NaOHCHI3 B无沉淀CHCNa. C2H5OH CrO3.(Py)2 CH3CHO CH3CHOH CNH+H2OCH3CHCOOH OHOb. CO Cl C无水 AlCl3c. O NaBH4H2O OH Hg+ , +稀 OHd. HC CH HH2OCH3CHOCH3CH=CHCHO H2 / Ni CH3CH2CH2CH2OHOHCH3e.Cl2CH2ClMgCH2MgCl1) CH3COCH3CH2CCH3光Et2O2)H+OCH3Of.CH3CH=CHCHOOHOH 无水 HClCH3CH=CHCHO3H3O+ CH CH-CHCHO稀 冷 KMnO4OHCH3CH-CHCHOH OHOOH OHMgHBrCH CH CH BrCH3CH2CH2MgBr1) HCHOg.CH3CH2CH2OH3 2 2Et2OCH3CH2CH2CH2OH2) H+8.5 ACH3CH2CHO + CH3MgBr BCH3CHO + CH3CH2MgBr8.6分别由苯及甲苯合成 2苯基乙醇