1、 有机化学（第四版，汪小兰）课后题答案 - 1 - 第一章 绪论 1.1 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。 1.3 C +6 2 4 H +1 1CCH4 中C中有4个电子与氢成键为SP3杂化轨道,正四面体结构CH4 SP3杂化HHHHC1s2s2p 2p2pyzx2pyxyz 2
2、pzxyz2pxxyz2sH1.4 a. C CHHHHC C HHH H或 b. HCHHCl c. HNHH d. H S He. HONOOf. OCH H g. O POOOHHHh. HCCHHHHHOPOOOH HH或i. HCCH j. O SOHHOOOSOOOH H或1.5 b.ClCCl HHc. H Br d.HCCl ClCle.H3COH H3COCH3f.1.6 电负性 O S , H2O与H2S相比，H2O有较强的偶极作用及氢键。 实用文章 http:/http:/ - 2 - 第二章 饱和脂肪烃 2.1 a. 2,4,4三甲基正丁基壬烷 butyl2,4,4tr
3、imethylnonane 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 5ethyl2methylheptane 2.2 a = b = d = e 为2,3,5三甲基己烷 c = f 为2,3,4,5四甲基己烷 2.3 a. 错，应为 2,
4、2二甲基丁烷Cb. c.d. e. f. 错，应为 2,3,3三甲基戊烷错，应为 2,3,5三甲基庚烷g. h.2.5 c b e a d 2.6 3 种 1 2 3ClClCl2.7 a是共同的 2.8 BrHHBrHHABHH BrBrHHCBrHHHBrHDBrH HBrHH2.10 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 3,5dimethyl3heptene d. 2,5二甲基己烯 2,5dimethyl2hex
5、ene 3.2 实用文章 http:/http:/ - 3 - a. 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. C2H5CHCCH2IH( Z )1碘2戊烯 ( E )1碘2戊烯CC2H5CCH2IHH d.CHCCH(CH3)2H( Z )4甲基2戊烯H3CCHCHCH(CH3)2H3C( E )4甲基2戊烯e.CH3CCHCH( Z )1,3戊二烯HCH2CHCHCH( E )1,3戊二烯H3CCH2f. CH
6、3CCHC( 2Z,4Z )2,4庚二烯HCH HC2H5CH3CCHCHCH C2H5H( 2Z,4E )2,4庚二烯CHCHCH3CCH C2H5H( 2E,4E )2,4庚二烯CHCHC( 2E,4Z )2,4庚二烯H3CCH HC2H53.5 完成下列反应式，写出产物或所需试剂 a. CH3CH2CH=CH2 H2SO4 CH3CH2CH CH3OSO2OHb. (CH3)2C=CHCH3 HBr (CH3)2C-CH2CH3Brc. CH3CH2CH=CH2BH3H2O2 OHCH3CH2CH2CH2OHd. CH3CH2CH=CH2H2O / H+ CH3CH2CH-CH3OHe.
7、 (CH3)2C=CHCH2CH3 O3Zn H2O,CH3COCH3 + CH3CH2CHOf. CH2=CHCH2OH Cl2 / H2O ClCH2CH-CH2OHOH1).2).1).2).3.6 1己烯正己烷Br2 / CCl4or KMnO4无反应褪色正己烷1己烯 3.7 实用文章 http:/http:/ - 4 - CH3CH=CHCH3 CH2=CHCH2CH3或 3.8 将下列碳正离子按稳定性由大至小排列： CCH3H3C CH CH3CH3+CCH3H3C CH CH3CH3 CCH3H3C CH2 CH2CH3+3.9 写出下列反应的转化过程： C=CHCH2CH2CH
8、2CH=CH3CH3CH+CH3CH3C-CH2CH2CH2CH2CH=CH3CH3CCH3CH3+ H+H_3.10 or3.11 a. 4甲基己炔 methyl2hexyne b. 2,2,7,7四甲基3,5辛二炔 2,2,7,7tetramethyl3,5octadiyne CH Cd.c. 3.13 a. HCCH LindlarcatH2CCH2 b. HCCH Ni / H2 CH3CH3c. HCCH + H2OHgSO4H2SO4CH3CHO d. HCCH + HClHgCl2 CH2=CHCle. H3CCCH HgBr2HBrCH3C=CH2BrHBrCH3-CBrBrC
9、H3f. H3CCCH + Br2 CH3C=CHBrBrg. H3CCCH + H2OHgSO4H2SO4CH3COCH3+ H2LindlarcatH3CCCH + H2h. H3CCCH + HBr HgBr2 CH3C=CH2Bri. CH3CH=CH2 HBr (CH3)2CHBr 3.14 实用文章 http:/http:/ - 5 - 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 正庚烷1,4庚二烯a.b. 2甲基戊烷2己炔1己炔Ag(NH3)2+灰白色无反应1己炔2己炔Br2 / CCl4褪色无反应2己炔2甲基戊烷
10、2甲基戊烷 3.15 a. CH3CH2CH2CCH HCl (过量) CH3CH2CH2CClClCH3b. CH3CH2CCCH3 +KMnO4 H+CH3CH2COOH + CH3COOHHgSO4H2SO4c. CH3CH2CCCH3 + H2O CH3CH2CH2COCH3 +CH3CH2COCH2CH3d. CH2=CHCH=CH2 + CH2=CHCHO CHOe. CH3CH2CCH + HCN CH3CH2C=CH2CN 3.16 CH3CHCH2C CHH3C 3.17 A H3CCH2CH2CH2CCH B CH3CH=CHCH=CHCH3 3.18 CH2=CHCH=C
11、H2 HBr CH3CHCH=CH2Br+ CH3CH=CHCH2BrCH2=CHCH=CH2 2HBr CH3CH CHBrCH3Br+ CH3CH CH2BrCH2BrCH2=CHCH2CH=CH2 HBr CH3CH CH2CH=CH2BrCH2=CHCH2CH=CH2 2HBr CH3CHBrCH2 CHBrCH3第四章 环烃 4.1 C5H10 不饱和度=1 实用文章 http:/http:/ - 6 - a. 环戊烷b.c.d.e.1甲基环丁烷顺1,2二甲基环丙烷反1,2二甲基环丙烷1,1二甲基环丙烷cyclopentane1methylcyclobutanecis1,2dimet
12、hylcyclopropanetrans1,2dimethyllcyclopropane1,1dimethylcyclopropanef. 乙基环丙烷 ethylcyclopropane4.3 a. 1,1二氯环庚烷 1,1dichlorocycloheptane b. 2,6二甲基萘 2,6 dimethylnaphthalene 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 acid f.CH3NO2Clg.CH3 C
13、H3h.2chloro4nitrotoluene2,3dimethyl1phenyl1pentene cis1,3dimethylcyclopentane4.4 完成下列反应： a.CH3HBrCH3Brb. + Cl2 高温 Clc. + Cl2ClClClCl+d.CH2CH3+ Br2 FeBr3 C2H5Br +BrC2H5e. CH(CH3)2+ Cl2 高温 C(CH3)2Cl实用文章 http:/http:/ - 7 - f.CH3 O3Znpowder , H2O CHOOg.CH3 H2SO4H2O ,CH3OHh. + CH2Cl2 AlCl3 CH2i.CH3+ HNO3
14、CH3NO2+CH3NO2j. + KMnO4 H+ COOHk. CH=CH2 + Cl2CH CH2ClCl 4.5 1. 24.6 CH3CH3CH3CH3+ Br2 FeBr3CH3CH3CH3CH3+BrBr+ Br2 FeBr3CH3CH3CH3CH3+BrBrCH3CH3+ Br2 FeBr3CH3CH3Br4.7 b , d有芳香性 4.8 实用文章 http:/http:/ - 8 - a. ABC1,3环己二烯苯1己炔Ag(NH3)2+C灰白色无反应 ABBr2 / CCl4无反应褪色BAb. AB环丙烷丙烯KMnO4无反应褪色AB 4.9 a. b. c.d. e. f.
15、Cl COOH NHCOCH3CH3NO2COCH3 OCH34.10 a. Br2FeBr3Br NO2HNO3H2SO4 Br b. HNO3H2SO4NO2Br2FeBr3BrO2Nc.CH32 Cl2FeCl3CH3ClCld.CH3+ Cl2 FeCl3CH3ClKMnO4COOHCl e.CH3KMnO4COOHCl2FeCl3COOHCl 实用文章 http:/http:/ - 9 - f. HNO3H2SO4 NO2CH3H3C2Br2FeBr3BrCH3BrNO2g. Br2FeBr3CH3 CH3BrKMnO4COOHBrHNO3H2SO4COOHBrNO24.11 可能为
16、 or or or oror or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。 4.12 H3C C2H54.13 Br BrA.4.14 A.BrClBrClBrBrClBrBrClB C D4.15 将下列结构改写为键线式。 a. b. c.d. e.OOOHor实用文章 http:/http:/ - 10 - 第五章 旋光异构 5.4 a. CH2 CH2CH2CH3OH BrCH2OHH BrCOOHH BrCOOHH BrCH2CH3( R )( 2R,3R )CH2OHBr HCH2CH3( S )b. HOOCCH CHBrCO
17、OHBr( meso- )COOHH BrCOOHBr HCOOHBr HCOOHH Br( 2S,3S )c. H3CCHBrCH COOHBrCOOHH BrCH3H BrCOOHBr HCOOHBr HCOOHH BrCOOHBr H( 2S,3R ) ( 2R,3S ) ( 2S,3S ) ( 2R,3R )COOHBr HCH3H Brd. CH3C=CHCOOHCH3 ( 无 ) 5.6 COOHH CH3CH2CH3( R )COOHH3C HCH2CH3( S )C5H10O25.7 =1C6H12A CH2=CHCHCH2CH3*CH3B CH3CH2CHCH2CH3CH3
18、5.10 ( I ) COOHH OHCH3( R )纸面上旋转 90 oOHHOOC CH3H( S )离开纸面旋转COOHHO HCH3( S )( 对映异构 )( 对映异构 )实用文章 http:/http:/ - 11 - 第六章 卤代烃 6.1 a. CH3CH-CHCH3CH3Brb. CCH3H3CCH3CH2I c.Brd.Cle.Cl Clf. 2碘丙烷 iodopropane g. 三氯甲烷 trichloromethane or Chloroform h. 1,2二氯乙烷 1,2dichloroethane i. 氯丙烯 chloro1propene j. 1氯丙烯 ch
19、loro1propene 6.4 写出下列反应的主要产物，或必要溶剂或试剂 a. C6H5CH2Cl MgEt2OC6H5CH2MgCl CO2 C6H5CH2COOMgCl H+H2OC6H5CH2COOHb. CH2=CHCH2Br + NaOC2H5 CH2=CHCH2OC2H5c.CH=CHBrCH2Br+ AgNO3EtOHr.tCH=CHBrCH2ONO2+ AgBrd. + Br2 KOH-EtOH CH2=CHCHO CHOBrBr KOH-EtOH光照Bre.CH2ClClNaOHH2OCH2OHClf. CH3CH2CH2CH2Br MgEt2OCH3CH2CH2CH2Mg
20、Br C2H5OH CH3CH2CH2CH3 + BrMgOC2H5g.CH3 Cl+ H2O OHSN2历程CH3OHh.ClCH3+ H2O OHSN1历程CH3OH+CH3OHi.BrKOH-EtOHj. CH2=CHCH2Cl CN CH2=CHCH2CNk. (CH3)3Cl + NaOH H2O (CH3)3COH 6.5 下列各对化合物按SN2历程进行反应,哪一个反应速率较快? 实用文章 http:/http:/ - 12 - a. (CH3)2CHI (CH3)3CCl b. (CH3)2CHI (CH3)2CHClc. CH2Cl Cl d. CH3CHCH2CH2Br CH
21、3CH3CH2CHCH2BrCH3e. CH3CH2CH2CH2Cl CH3CH2CH=CHCl 6.6 将下列化合物按SN1历程反应的活性由大到小排列 b c a 6.7 (a) 反应活化能 (b) 反应过渡态 (c) 反应热 放热 6.8 A 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. Br2 6.10 CH3CHCH2BrCH3KOH-EtOH CH3C=CH2CH3H+H2O CH3 CCH3CH3OHa.b.CH3 CCH3CH3
22、BrHBrCH3 CCH3CH2BrBrBr2HOBrCH3 CCH3CH2BrOHd. c. e. 6.11 A BrCH2CH2CH3 B. CH2=CHCH3 C. CH3CHBrCH3 实用文章 http:/http:/ - 13 - 第七章 醇 酚 醚 7.1 命名下列化合物 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 4phenyl2pentanol e. (1R,2R)2甲基环己醇 (1R,2R)2methylcyclohexanol f. 乙二醇二甲醚 et
23、hanediol1,2dimethyl ether g. (S)环氧丙烷 (S)1,2epoxypropane h. 间甲基苯酚 mmethylphenol i. 1苯基乙醇 1phenylethanol j. 4硝基1萘酚 4nitro1naphthol 7.3 完成下列转化 a.OHCrO3.Py2Ob. CH3CH2CH2OH 浓 H2SO4 CH3CH=CH2 Br2Br BrCH3CH-CH2 KOH / EtOHc. A CH3CH2CH2OH (CH3)2CHBr CH3CH2CH2OCH(CH3)2H+CH3CH=CH2 HBr CH3CHCH3BrCH3CCHNaB. CH3
24、CH2CH2OH HBrH+CH3CH=CH2 HOHCH3CH2CH2BrCH3CHCH3OHd. CH3CH2CH2CH2OH CH3CH2CH=CH2 HOH CH3CH2CHCH3OHe.OH浓 H2SO4OHSO3Hf. CH2=CH2 稀 冷 KMnO4 CH2-CH2OH OHO2 HOCH2CH2OCH2CH2OCH2CH2OHClCH2CH2OH HOCH2CH2OCH2CH2OCH2CH2OHH2O+Cl2ClCH2CH2OHg. CH3CH2CH=CH2B2H6 Et2OH2O2 OH CH3CH2CH2CH2OHh. ClCH2CH2CH2CH2OH NaOHONaOH
25、H+Na CH3CHCH3ONaCH3CH2CH2Br T.MHBr CH3CH2CH2CH2BrNaOHCH3CH2OH1)2),H+7.5 下列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 实用文章 http:/http:/ - 14 - a, NOOOHcis NOOO HtransNOHO OOHNOOb.OHOH2CH3C CH3d.OOH7.6 写出下列反应的历程 OH H+ +OH2abab+ H+H+_ H2OH_7.7 写出下列反应的产物或反应物 a. (CH3)2CHCH2CH2OH + HBr (CH3)2CHCH2CH2Brb.
26、OH + HCl 无水 ZnCl2 Clc.OCH3CH2CH2OCH3+ HI (过量)CH2CH2+ CH3d.O CH3+ HI (过量)e. (CH3)2CHBr + NaOC2H5 (CH3)2CHOC2H5 + CH3CH=CH2f. CH3(CH2)3CHCH3 KMnO4OHCH3(CH2)3COCH3g. CH3COCHOHCH2CH3 HIO4 CH3COOH + CH3CH2CHOh.CH3OHOHHIO4 CH3COCH2CH2CHOi.OHCH3+ Br2OHCH3Br BrCCl4 , CS2 中单取代OHj. CH3(CH2)2CHOHCH2CH3 浓分子内脱水H
27、2SO4 CH3CH2CH=CHCH2CH3 +CH3CH2CH2CH=CHCH37.8 实用文章 http:/http:/ - 15 - A OCH3 B. OH C. CH3I第八章 醛、酮、醌 8.1 a. 异丁醛 甲基丙醛 methylpropanal isobutanal b. 苯乙醛phenylethanal c. 对甲基苯甲醛 pmethylbenzaldehyde d. 3甲基丁酮 methylbutanone e. 2,4二甲基戊酮 2,4dimethyl3pentanone f. 间甲氧基苯甲醛 mmethoxybenzaldehyde g. 甲基丁烯醛3methyl2bu
28、tenal h. BrCH2CH2CHO i. OOj. CCl3CH2COCH2CH3 k. (CH3)2CCHO l. CH3CH2COCH2CHOm. CH=CHCHO n. CCH3Oo. 丙烯醛 propenalp. 二苯甲酮 diphenylKetone 8.3 写出下列反应的主要产物 a. CH3COCH2CH3 + H2NOH CH3CCH2CH3N OHb. Cl3CCHO + H2O Cl3CCHOHOHc. H3C CHO HOOC COOH+ KMnO4 H+d. CH3CH2CHO 稀 NaOH CH3CH2CH-CHCHOOHCH3e. C6H5COCH3 + C6
29、H5MgBr C6H5CC6H5CH3OMgBr H+H2OC6H5CC6H5CH3OHf. O + H2NNHC6H5 NNHC6H5g. (CH3)3CCHO 浓 NaOH (CH3)3CCH2OH (CH3)3CCOOH+h.O+ (CH3)2C(CH2OH)2 无水 HClO OOi. + K2Cr2O7 H+HOOC(CH2)3COOHj. CHO KMnO4室温COOH 实用文章 http:/http:/ - 16 - k. COCl2 ,H2OOHCOCH2ClCH3 COOH + CHCl3l. COCH3 + Cl2 H+m. CH2=CHCH2CH2COCH3 + HCl
30、CH3-CHCH2CH2COCH3Cl+Cl OHCH3n. CH2=CHCOCH3 + HBr BrCH2CH2COCH3o. CH2=CHCHO + HCN NCCH2CH2CHO + CH2=CHCHCNOHp. C6H5CHO + CH3COCH3 稀 NaOH C6H5CHCH2C-CH3OOH 8.4 a. A 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Tollen 试剂沉淀 A无沉淀 BCI2 / NaOHCHI3无沉淀BC 8.4 完成下列转化 a. C2H5O
31、H CrO3.(Py)2 CH3CHO CH3CHOHCNH+ CH3CHCOOHOHb. COCl无水 AlCl3COc. O NaBH4 OHd. HC CH H+Hg+ ,H2OCH3CHO 稀OHCH3CH=CHCHO H2 / Ni CH3CH2CH2CH2OHe.CH3Cl2光CH2Cl MgEt2OCH2MgClH+CH3COCH3 CH2CCH3OHCH3f. CH3CH=CHCHO OHOH 无水 HCl CH3CH=CHCH OO稀冷 KMnO4OHOOCH3CH-CHCHOHOHH3O+ CH3CH-CHCHOOHOHg. CH3CH2CH2OH HBr CH3CH2CH
32、2BrMgEt2OCH3CH2CH2MgBr HCHOH+CH3CH2CH2CH2OHHCNH2OH2O1)2)1)2) 8.5 A CH3CH2CHO + CH3MgBr B CH3CHO + CH3CH2MgBr 8.6 分别由苯及甲苯合成2苯基乙醇 实用文章 http:/http:/ - 17 - CH3Cl2光照CH2Cl MgEt2OCH2MgCl HCHOH+CH2CH2OH1)2)Br MgBrOH+Br2FeMgEt2O H2O 8.8 a. 缩酮 b. 半缩酮 c.d 半缩醛 8.9 b. H3COOH+ CH3CHO + HOCH2CH2OH+ OHa.OOHOHOHOOH
33、OHOc.H+ OHOHOHHOH+ OHOHOHHO8.10 A. CHH3CCH CH3OHB. CHH3CC CH3H3C H3C O C.CH3CCH CH3H3C8.11 O CH38.12 A CH3CH-C-CH2CH3CH3OB. H3CCHH3CCHCH2CH3OHC. H3CCH3CCHCH2CH3D. CH3CH2CHO E. CH3COCH3 8.13 O O O OBr BrHOOC COOHA B C D 实用文章 http:/http:/ - 18 - 第九章 羧酸及其衍生物 9.1 a. 2甲基丙酸 2Methylpropanoic acid (异丁酸 Isob
34、utanoic acid ) b. 邻羟基苯甲酸（水杨酸）oHydroxybenzoic acid c. 2丁烯酸 2Butenoic acid d 3溴丁酸 3Bromobutanoic acid e. 丁酰氯 Butanoyl Chloride f. 丁酸酐 Butanoic anhydride g. 丙酸乙酯 Ethyl propanoate h. 乙酸丙酯 Propyl acetate i. 苯甲酰胺 Benzamide j. 顺丁烯二酸 Maleic acid s. COt. H3C COk.COOCH3COOCH3l. HCOOCH(CH3)2 m. CH3CH2CONHCH39.
35、2 g a b c f e h d 9.3 写出下列反应的主要产物 a. Na2Cr2O7-H2SO4 COOHCOOH +COOHCOOHb. (CH3)2CHOH + COOCH(CH3)2H3CCOClH3Cc. HOCH2CH2COOH LiAlH4 HOCH2CH2CH2OHd. NCCH2CH2CN + H2O NaOH OOCCH2CH2COO H+HOOCCH2CH2COOHe. CH2COOHCH2COOH Ba(OH)2Of. CH3COCl +CH3无水 AlCl3CH3COCH3+CH3COCH3g. (CH3CO)2O + OH OCOCH3h. CH3CH2COOC
36、2H5 NaOC2H5 CH3CH2COCHCOOC2H5CH3 i. CH3COOC2H5 + CH3CH2CH2OH H+ CH3COOCH2CH2CH3 + C2H5OHj. CH3CH(COOH)2 CH3CH2COOHk. COOH + HCl ClCOOH+ CO2实用文章 http:/http:/ - 19 - l. 2 + HOCH2CH2OHH+ COOCH2CH2OOCm.COOHLiAlH4CH2OHCOOHn. HCOOH +OH HCOOH+o. CH2CH2COOC2H5CH2CH2COOC2H5NaOC2H5OCOOC2H5p.NCONH2OHNCOO+ NH3q
37、. CH2(COOC2H5)2 + H2NCONH2 HN NHOO O 9.4 a. KmnO4 b. FeCl3 c. Br2 or KmnO4d.FeCl3 2,4-二硝基苯肼或I2 / NaOH 9.5 完成下列转化： a. OCNOHH+ COOHOHb. CH3CH2CH2Br CN CH3CH2CH2CNH+ CH3CH2CH2COOHc. (CH3)2CHOH CrO3.(Py)2 (CH3)2CO (CH3)2C CNOHH+ (CH3)2C COOHOHd.CH3CH3KMnO4COOHCOOHCOOHCOOHBa(OH)2OOOOOOe. (CH3)2C=CH2 HBr
38、(CH3)3CBr MgEt2O(CH3)3CMgBr CO2H+ / H2O(CH3)3CCOOHf. CH3BrAlCl3 CH3KMnO4 COOH Br2FeCOOHBrg. HC CH H2OH+ Hg2+,CH3CHO KMnO4 CH3COOHCH3CH2OHH+CH3COOC2H5HCNH2OHCN1)2)H2OH2O实用文章 http:/http:/ - 20 - h.OHNO3 HOOC(CH2)4COOH Oi. CH3CH2COOH LiAlH4 CH3CH2CH2OH HBr CH3CH2CH2Br MgEt2O CH3CH2CH2MgBrOH+CH3CH2CH2CH
39、2CH2OH KMnO4 CH3CH2CH2CH2COOH或 CH3COCH2COOC2H5 EtONaCH3CH2CH2Br CH3 COCHCH2CH2CH3COOC2H5 浓 OHCH3(CH2)3COOHj. CH3COOH Cl2PCH2COOHClCN CH2COOHCNEtOHH+ , CH2(COOC2H5)2k.OOONH3 CH2COONH4CH2CONH2l. CO2CH3OHH+H2OCOOHOH(CH3CO)2O COOHOOCCH3m. CH3CH2COOH SOCl2 CH3CH2COCl OH CH3CH2COOn. CH3CH(COOC2H5)2 OHH+ C
40、H3CH2COOH1)2)H3O+1)2) 3) 9.6 己醇 A已酸 B对甲苯酚 CNaHCO3 水溶液水相 已酸钠 HCl 已酸 B有机相 已醇对甲苯酚NaOH水相有机相 已醇 A酚钠 HCl 酚C9.7 COOHCOOHCOOHCOOHCOOHCOOHCOOHHOOCHOOC COOHH CH3 CH2COOHHOOC(Z)易成酐 (E) 不易 (Z) 易成酐 (E) 不易成酐 9.8 A. CH2COOHCH2COOHB. OOOC. H2CH2C COCH3COCH3OOD. CH2CH2OHCH2CH2OH实用文章 http:/http:/ - 21 - 第十章 取代酸 10.1
41、m. 3-氯丁酸（3-Chlorobutanoic acid） n. 4-氧代戊酸（4oxopentanoic acid) 10.2 a. CH3CH2CH2COCH2COOCH3 (A)OHCOOH(B)CH3CHCOOHOH(C)FeCl3CAB显色不显色Na2CO3AB溶解，有气体无变化10.3 写出下列反应的主要产物： a. CH3COCHCOOC2H5CH3稀OH-H+ , H2O CH3COCH2CH3b. CH3COCHCO2CH3CH2CO2CH3浓 NaOH CH2COOCH2COOc. CH3CH2CHCOOHOH HCOC CHOCOOCH3CH2CH2CH3d.COOC
42、H3COCH3 稀 H+ C CH31)2)_ + CH3COO + CH3OH_+ CO2 + CH3OHOe.OCH2CH2CH3COOHOCH2CH2CH3f. HOOCCH2COCCOOHCH3CH3CH3COCH(CH3)2g. CH3CH2CHCOOHClNaOH-H2O CH3CH2CHCOONaOHh. CH3CHCH2COOHOHCH3CH=CHCOOHOOCH3NaOH-H2O CH3CHCH2COONaCH2OHi.+ CO2j. CH3CH2CCOOHOHCH3 稀 H2SO4k. CH3CH2COCO2H 稀H2SO4CH3CH2CHO + CO2CH3CH2CCH3
43、 + HCOOHOl. CH3CHCOCO2HCH3CH3CHCOOHCH3+ CO实用文章 http:/http:/ - 22 - m. COOHCOOHCOOHOOOn.O ONaOH,HCl, O Oo, CH3CH2COOH + Cl2 P CH3CHCOOHCl1)2)10.5 完成下列转化： a. BrCH2(CH2)2CH2CO2H NaOHO Ob.OCO2CH3 EtOC2H5ClCH2COCH3OCO2CH3CH2COCH3稀OH-H+OCH2COCH3c. CH3COOH CH3CH2OHH+CH3COOC2H5 NaOC2H5 CH3COCH2COOC2H5NaOC2H
44、5BrCH2CH2CH2BrCH3 COC COOC2H5 OH-H+CH3CO1)2) ,1)2)2)1),d. CH3COOC2H5 NaOC2H5 CH3COCH2COOC2H5 NaOC2H5BrCH3CH3COCHCOOC2H5CH3NaOC2H5CH3CHCOOC2H5BrCH3CCOOOC2H5COCH3CH3CHCOOC2H5浓OH CH3CHCOOHCH3CHCOOH1)2)2)1) 1)2),H+_实用文章 http:/http:/ - 23 - 第十一章 含氮化合物 11.2 a. 硝基乙烷 b. p亚硝基甲苯 c. N乙基苯胺 d. 对甲苯重氮氢溴酸盐或溴化重氮对甲苯 e. 邻溴乙酰苯胺 f. 丁腈 g. 对硝基苯肼 h. 1,6己二胺 i. 丁二酰亚胺 j. 亚硝基二乙胺 k. 溴化十二烷基苄基二甲铵(CH3)3N+CH2CH2OHOH m. HOHOCH2CH2NH2
