2022年有机化学汪小兰第四版课后习题答案 .pdf

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1、H N Cl 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 杂化轨道,正四面体结构H 1

2、.4 CH4 SP3 杂化C H H H Ha. HC C H 或H C C Hb. c.H C ClH d. H S HH H H H HO O OH O H H e. H O Nf. g. H O PO H 或H O P O Hh. H C C HO H C HO O H HH H O O1.5 i. H C C H j.ClH O S O H 或O HH O S O H O b. c. H Br d. e.C C O f. O H Cl ClH ClH3C H H3CCH31.6 电负性O S , H2O 与 H2S 相比， H2O 有较强的偶极作用及氢键。精选学习资料 - - - -

3、- - - - - 名师归纳总结 - - - - - - -第 1 页，共 38 页C第二章饱和脂肪烃2.1 a. 2,4,4三甲基正丁基壬烷 butyl 2,4,4trimethylnonane 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5ethy

4、l2methylheptane 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2.3a. 错，应为2,2二甲基丁烷C b. 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 d 2.6Cl Cl3 种1 2 32.7 a 是共同的2.8 BrBr BrClBrH BrH 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 ethyl1 but

5、ene b. 2丙基己烯propyl1hexene c. 3,5二甲基庚烯3,5dimethyl 3heptene d. 2,5二甲基己烯2,5dimethyl2hexene 3.2 精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 2 页，共 38 页C 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. C2H5 C H CH2I C H H C C2H5CH2I d.C

6、 H H3C C H CH(CH3)2C H H3C C H H C CH(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 H3C C C CH2C C H HCH2H3C2 5 C C H( Z ) 1,3戊二烯( E ) 1,3 戊二烯H H( 2Z,4Z )2,4 庚二烯H H C C H H3C C C H3C HC C H C CC2H5H3C H C C H H C C H C2H5( 2Z,4E ) 2,4庚二烯H H ( 2E,4Z ) 2,4庚二烯H C2H5( 2E,4E

7、 ) 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 CH3OSO2OH HBr (CH3)2C-CH2CH3b. (CH3)2C=CHCH3c. CH3CH2CH=CH21). BH32).H2O2 , OHBr CH3CH2CH2CH2OH H2O / H+ CH CH CH-CHd. CH3CH2CH=CH21). O33 2 3 OH e. (CH3)2C=CHCH2CH32). Zn , H2O CH3COCH3 + CH3CH2CHOf. CH2=CHCH2OH Cl2 / H2O ClCH2CH-CH2OH OH

8、 3.6 3.7 1己烯正己烷Br2 / CCl4or KMnO4无反应褪色正己烷1己烯精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 3 页，共 38 页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 CH2+3.9 写出下列反应的转化过程：CH3CH3H3C H3C C=CHCH2CH2CH2CH=C CH3 H+ CH3H3C H3C +C-CH2CH2CH2CH2CH=CCH3CH33.10+ _

9、 H+ H or3.11 a. 4甲基己炔 methyl2hexyne b. 2,2,7,7四甲基 3,5 辛二炔2,2,7,7tetramethyl3,5octadiynec. 3.13 a. HC CH + Hd. LindlarCH C H2C CH2 b. HC CH Ni / H2 CH CH2catH2SO43 3HgCl2c. HC CH + H2OHgSO4CH3CHO d. HC CH + HClBrCH2=CHCle. H3CC CHHgBr2HBrCH3C=CH2BrHBrCH3-C BrCH3f. H3CC CH + Br2 CH3C=CHBrBrg. H3CC CH

10、+ H2OH2SO4HgSO4CH3COCH3h. H3CC CH + HBr HgBr2 CH3C=CH2BrLindlarHBri.3.14 H3CC CH + H2catCH3CH=CH2(CH3)2CHBr精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 4 页，共 38 页3 2 2 3 2 3 2 2 + + a. 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3.15Ag(NH3)2灰白色无反应1己炔2甲基戊烷2己炔Br2 / C

11、Cl4褪色无反应2己炔2甲基戊烷a. CH CH CH C CHHClCl(过量) CH3CH2CH2C ClCH3H+b. CH3CH2C CCH3 + KMnO4CH3CH2COOH + CH3COOHc. CH CH C CCH+ H OH2SO43 2 3 2HgSO4CH3CH2CH2COCH3 + CH3CH2COCH2CH3d. CH2=CHCH=CH2 + CH2=CHCHO CHOe. CH3CH2C CH + HCN CH3CH2C=CH2CN3.16 CH3CHCH2C CH H3C3.17 A H3CCH2CH2CH2C CH B CH3CH=CHCH=CHCH33.1

12、8CH2=CHCH=CH2HBr CH CHCH=CH Br+ CH3CH=CHCH2BrCH2=CHCH=CH22HBr CH3CH CHCH3+ CH3CH CH2CH2BrBrBr BrCH2=CHCH2CH=CH2HBr CH CHCH CH=CH Br CH2=CHCH2CH=CH22HBrCH3CH Br CH2 CHBrCH34.1 C5H10 不饱和度 =1 第四章环烃精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 5 页，共 38 页a. 环戊烷b. 1甲基环丁烷cyclopentane1methylcyclobutanec. 顺

13、 1,2二甲基环丙烷cis1,2dimethylcyclopropaned.反 1,2二甲基环丙烷trans 1,2dimethyllcyclopropanee. 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1,1 dichlorocycloheptane b. 2,6二甲基萘2,6dimethylnaphthalene c. 1甲基异丙基1,4环己二烯1isopropyl 4 methyl1,4 cyclohexadiene d. 对异丙基甲苯p isopropyltoluene e. 氯苯磺

14、酸 chlorobenzenesulfonic acidCH3Cl f. 2chloro 4nitrotoluene g.NO22,3 dimethyl 1phenyl 1penteneCH3 CH3 h. cis1,3 dimethylcyclopentane 4.4 完成下列反应：CH3CH3a. HBr Brb. + Cl2c. + Cl2CH2CH3高温ClCl + Cl Cl Cl Br C2H5d. + Br2 FeBr3 BrC2H5 +e. CH(CH3)2+ Cl2Cl 高温C(CH3)2精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - -

15、-第 6 页，共 38 页CH3 OO3f. Znpowder , H2O CHOCH3g. H2SO4H2O , CH3OH h. + CH2Cl2CH3AlCl3 CH2 CH3CH3NO2i. + HNO3 +NO2+j. + KMnO4 H COOHk. 4.5CH=CH2+ Cl2CH CH2Cl Cl 1. 24.6 CH3CH3CH3+ Br2FeBr3CH3Br CH3CH3+CH3CH3CH3Br CH3+ Br2FeBr3+ CH3BrBr CH3CH3+ Br2FeBr3CH3Br CH34.7 b , d 有芳香性4.8 CH3精选学习资料 - - - - - - -

16、- - 名师归纳总结 - - - - - - -第 7 页，共 38 页2 a. AB1,3 环己二烯苯Ag(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B4.9 Cl COOH NHCOCH3a. b. c.CH3COCH3 OCH3d. e. f.NO24.10 a. Br2FeBr3Br HNO3 BrH2SO4NO2b. HNO3H2SO4NO2Br2FeBr3Br O2NCH3c. CH3d. 2 Cl2FeCl3+ Cl2CH3Cl Cl FeCl3CH3ClKMnO4COOH Cl CH3e. KMnO4C

17、OOH Cl2FeCl3COOH Cl 精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 8 页，共 38 页CH3f.HNO3H2SO4H3CNO2Br2Br2FeBr 3CH3BrNO2CH3 CH3 g. Br2KMnO4COOHHNO3COOH4.11FeBr3BrH2SO4BrNO2Br可能为or or or oror or4.12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 Br4.14 Br Br Br BrCl BrA. B C DBrCl Cl C

18、l4.15 将下列结构改写为键线式。a. b. c. orO O d. O e. H精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 9 页，共 38 页5.4第五章旋光异构a. CH2 CH2CH2CH3OH Br CH2OH H Br CH2CH3( R )CH2OH Br H CH2CH3( S ) b. HOOCCH CH COOH COOH H Br COOH H Br COOH Br H Br BrH Br COOH ( meso- ) Br H COOH ( 2S,3S ) H Br COOH ( 2R,3R )c. H3CCH Br

19、CH COOH Br COOH H Br H Br CH3COOH Br H Br H COOH COOH H Br Br H COOH COOH Br H H Br CH3( 2S,3R ) ( 2R,3S ) ( 2S,3S ) ( 2R,3R )d. CH3C=CHCOOH CH35.6( 无 ) 5.7C5H10O2 COOH H CH3CH2CH3( R ) COOH H3C H CH2CH3( S ) C6H12 =1*5.10A CH2=CHCHCH2CH3CH3B CH3CH2CHCH2CH3CH3( I ) COOH H OH CH3( R ) 纸面上旋转90 oOH HOO

20、C CH3H ( S ) COOH ( 对映异构 ) 离开纸面旋转HO H CH3( S ) ( 对映异构 ) 精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 10 页，共 38 页第六章卤代烃6.1 BrCH3Br Cla. CH3CH-CHCH3CH3b. H3CC CH3CH2I c.d. Cl Cl e.f. 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 chlo

21、ro1propene6.4 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. C6H5CH2ClEt2OC6H5CH2MgCl6 5 2H2O6 5 2b. CH2=CHCH2Br + NaOC 2H5 CH2=CHCH2OC2H5 CH=CHBrc. CH2Br+ AgNO3EtOHr.tCH=CHBrCH2ONO2+ AgBrBr光照CH2=CHCHO CHOd. + Br2 KOH-EtOHCH2Cl e.ClNaOH H2OBrBrCH2OHClf. CH3CH2CH2CH2Br MgCH CH CH CH MgBr C2

22、H5OHEt2Og.3 2 2 2 OHCH3CH2CH2CH3 + BrMgOC2H5 CH3 ClCH3h.+ H2O OHSN2 历程CH3CH3OH CH3+ H2O OH+SN1 历程Cl OH Br i. KOH-EtOHj. CH2=CHCH2Cl CNCH2=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?精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 11 页，共 38 页a. (CH3)2CHI (CH3)3CCl b. (CH3

23、)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 a 6.7 (a) 反应活化能(b) 反应过渡态(c) 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. Br26.10 CH3CH3CHCH2BrCH3CH3KOH-EtOH

24、CH3C=CH2CH3a. HBrCH3H+H2O CH3 C OHb.CH3CH3CH3 C BrCH2BrCH3 C BrCH3CH3C CH2OH Brd. c. e.6.11 A BrCH2CH2CH3 B. CH2=CHCH3 C. CH3CHBrCH3精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 12 页，共 38 页3 2 7.1 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4phenyl2

25、pentanol e. (1R,2R) 2 甲基环己醇(1R,2R) 2 methylcyclohexanol f. 乙二醇二甲醚ethanediol 1,2 dimethyl ether g. (S) 环氧丙烷(S) 1,2 epoxypropane h. 间甲基苯酚m methylphenol i. 1苯基乙醇1phenylethanol j. 4硝基 1 萘酚4nitro1naphthol7.3 完成下列转化OH Oa. CrO3.Py2b. CH3CH2CH2OH 浓H2SO4 CH3CH=CH2Br2CH3CH-CH2Br Br KOH / EtOH CH C CHc. A CH3C

26、H2CH2OH H+ CH3CH=CH2Na HBr (CH3)2CHBr CH3CH2CH2OCH(CH3)2BrCH3CHCH3B. CH3CH2CH2OH H+ CH3CH=CH2HBr HOH H+ CH3CH2CH2Br OHNaCH3CHCH3ONaCH3CHCH3CH3CH2CH2Br T.M OHd. CH3CH2CH2CH2OHHBr CH3CH2CH2CH2BrCH3CH2OHCH3CH2CH=CH2HOH CH CH CHCHOH OHe. 浓H2SO4NaOH H+ 3 2 3SO3H f. CH2=CH2 稀 冷 KMnO4 CH -CH OHOCH CH OCH C

27、H OCH CH OH2 2 2 2 2 2 2 2H2O+Cl2ClCH2CH2OHOH OHClCH2CH2OH HOCH2CH2OCH2CH2OCH2CH2OHNaOH g. CH3CH2CH=CH21) B2H6 ,Et2O 2)H2O2 ,OHCH3CH2CH2CH2OH h. ClCH2CH2CH2CH2OH NaOH O7.5 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 可以形成精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 13 页，共 38 页Oa, N O HO b. H3CH2C CH3OO

28、Hcis N O O O H transd.O OH H O O H N NO O O O7.6 写出下列反应的历程OH H+OH2a a _ H2O +b b +_ H+ _ H+H 7.7 写出下列反应的产物或反应物a. (CH3)2CHCH2CH2OH + HBr (CH3)2CHCH2CH2Brb. OH + HCl 无水ZnCl2 ClOCH3c.+ HI (过量 )+ CH3CH2CH2OCH3d. + HI (过量 ) O CH3CH2CH2e. (CH3)2CHBr + NaOC2H5 (CH3)2CHOC2H5 + CH3CH=CH2f. CH3(CH2)3CHCH3 KMn

29、O4CH3(CH2)3CCH3OH OHOg. CH3CCH CH2CH3 HIO4 CH COOH + CH CH CHOO OH3 3 2CH3h. OHHIO4 CH COCH CH CHOOH 3 2 2OH OHi. + Br2Br BrCCl4 , CS2 中单取代CH3j. CH3(CH2)2CHCH2CH3 浓CH3H2SO4 CH CH CH=CHCH CH+ CH CH CH CH=CHCH7.8 3 2 OH 分子内脱水2 3 3 2 2 3 精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 14 页，共 38 页3pentan

30、one f. 间甲氧基苯甲醛m methoxybenzaldehydeg. 甲基丁烯醛3methyl2butenalh. BrCH2CH2CHOO+ AOCH3B.OHC. 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 methyl butanone e. 2,4二甲基戊酮2,4 dimethyl i. Oj. CCl3CH2COCH2CH3 k. (CH3)2CCHO l. CH3CH2COCH2CHOm. CH=C

31、HCHO n. C CH3Oo. 丙烯醛propenal p. 二苯甲酮diphenyl Ketone 8.3 写出下列反应的主要产物OH N a. CH3COCH2CH3 + H2NOH CH3CCH2CH3OHb. Cl3CCHO + H2O Cl3CCHOH H+c. H3C CHO + KMnO4HOOC COOH OHd. CH3CH2CHO 稀 NaOH CH3CH2CH-CHCHO CH3CH3H+CH3e. C6H5COCH3 + C6H5MgBr C6H5COMgBr H2OC6H5C OHC6H5f. O + H2NNHC6H5 NNHC6H5C6H5g. (CH3)3CC

32、HO 浓NaOH (CH3)3CCH2OH+ (CH3)3CCOOH O h. O+ (CH3)2C(CH2OH)2 无水 HClOi. O+ K2Cr2O7 HHOOC(CH2)3COOH j. CHO KMnO4 COOH室温精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 15 页，共 38 页HCN3 f. CH3CH=CHCHOOk. COCH3Cl2 , H2O OH+COOH + CHCl3O l. CCH3 + Cl2 HC CH2ClClCl OHm. CH2=CHCH2CH2COCH3 + HCl CH3-CHCH2CH2COCH

33、3 +CH3n. CH2=CHCOCH3 + HBr BrCH2CH2COCH3 OHo. CH2=CHCHO + HCN NCCH2CH2CHO + CH2=CHCHOCN8.4p. C6H5CHO + CH3COCH3稀NaOHC6H5CHCH2C-CH3OH 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8.4 完成下列转化Tollen 试剂沉淀A无沉淀B C I2 / NaOH CHI3 B无沉淀Ca. C2H5OH CrO3.(Py)2 CH3CHO CH3CHO

34、H CNH+ H2OCH3CHCOOH OHOb. CO Cl C无水AlCl3c. O NaBH4H2O OHHg+ , +稀OH d. HC CH HH2OCH3CHOCH3CH=CHCHO H2 / Ni CH3CH2CH2CH2OHOHCH3e. Cl2CH2Cl MgCH2MgCl 1) CH3COCH3CH2CCH3光Et2O 2) H+OCH3OOHOH 无水HCl CH3CH=CHCHOH3O+ CH CH-CHCHO 稀 冷 KMnO4OHCH3CH-CHCH OH OH OOH OHMgHBr CH CH CH BrCH3CH2CH2MgBr1) HCHOg. CH3CH2

35、CH2OH 3 2 2 Et2OCH3CH2CH2CH2OH2) H+8.5 A CH3CH2CHO + CH3MgBr B CH3CHO + CH3CH2MgBr 8.6 分别由苯及甲苯合成2苯基乙醇精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 16 页，共 38 页O + CH3Cl2光照CH2Cl MgEt2OCH2MgCl1) HCHO2) H+CH2CH2OHBr2FeBr MgBrOMg H+Et2O H2O8.8 a. 缩酮b. 半缩酮c.d 半缩醛8.9OH OHO +a. HOH OHOHb. H3COH+CH3CHO + HO

36、CH2CH2OHOH OHOH Oc. OH OH OHOH+ OH OH OH8.10H3C H3C O H CA. CHH3C 8.11CH CH3OH B.CH H3C C CH3C. 3C H3C CH CH3O CH38.12O A CH3CH-C-CH2CH3CH3B. H3CCH H3CCHCH2CH3OHC. H3C C H3CCHCH2CH38.13D. CH3CH2CHO E. CH3COCH3O O O OBr Br HOOC COOH A B C D精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 17 页，共 38 页+ +

37、 第九章羧酸及其衍生物9.1 a. 2甲基丙酸2Methylpropanoic acid (异丁酸Isobutanoic acid ) b. 邻羟基苯甲酸（水杨酸）oHydroxybenzoic acid c. 2丁烯酸2Butenoic acidd 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 COOCH3k.COOCH3Ol.

38、HCOOCH(CH3)2 m. CH3CH2CONHCH3Os. Ct. H3C C9.2 g a b c f e h d 9.3 写出下列反应的主要产物a. Na2Cr2O7-H2SO4 COOH + COOH COOH COOH b. (CH3)2CHOH + H3C COCl H3C COOCH(CH 3)2c. HOCH2CH2COOH LiAlH4 HOCH2CH2CH2OHd. NCCH2CH2CN + H2O NaOH OOCCH CH COOHHOOCCH CH COOH2 2 2 2 CH2COOH e.CH2COOH Ba(OH) 2O CH3COCH3CH3f. CH3C

39、OCl +CH3无水AlCl3+ COCH3g. (CH3CO)2O + OH OCOCH 3h. CH3CH2COOC 2H5 NaOC 2H5 CH3CH2COCHCOOC 2H5CH3i. CH3COOC2H5 + CH3CH2CH2OH Hj. CH3CH(COOH)2 CH3CH2COOH Cl k. CH3COOCH2CH2CH3 + C2H5OH+ CO2COOH + HClCOOH 精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 18 页，共 38 页+ + Nl. 2COOH+ HOCH2CH2OHCOOCH CH OOCm.CO

40、OHLiAlH4H+ 2 2CH2OHn.HCOOH + OH HCOO Ho. CH2CH2COOC2H5CH2CH2COOC2H5CONH2NaOC2H5OCOOC2H5COO p.N OH+ NH3Oq. CH2(COOC2H5)2 + H2NCONH2 HN NHO O9.4 a. KmnO4 b. FeCl3 c. Br2 or KmnO4d.FeCl3 2,4-二硝基苯肼或I2 / NaOH9.5 完成下列转化：a. OHCN CN H+ COOH OH H2O OHb. CH3CH2CH2Br CNCH3CH2CH2CN H H2O CH3CH2CH2COOH + c. (CH3

41、)2CHOH CrO3.(Py)2 (CH3)2C OHCN (CH3)2C CN OH H H2O(CH3)2C COOHOH CH3d. CH3KMnO4COOH COOH COOH COOH Ba(OH)2O OO O O O 1) CO2e. (CH3)2C=CH2 HBr (CH3)3CBr MgEt2O(CH3)3CMgBr (CH3)3CCOOH 2) H+ / H2Of. CH3Br AlCl3CH3 KMnO4 COOH Br2Fe BrCOOH g. HC CH H2OCH CHO KMnOCH3CH2OH3H+ , Hg2+4 CH3COOH H+CH3COOC2H5精选

42、学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 19 页，共 38 页+ Oh. HNO3 HOOC(CH2)4COOH Oi. CH3CH2COOH LiAlH4 CH3CH2CH2OH HBr CH3CH2CH2BrKMnO4Mg Et2O CH3CH2CH2MgBr O CH3CH2CH2CH2CH2OH H+ CH3CH2CH2CH2COOH 或CH3COCH2COOC2H51) EtONaCH CO CH COOC H浓OH32) CH3CH2CH2Br2 5 CH2CH2CH3CH3(CH2)3COOHj. CH3COOH Cl2PCH2C

43、OOH Cl CNCH2COOH CN H3O+EtOHH+ , CH2(COOC2H5)2Ok.O NH3 CH2COONH4O CH2CONH2CO2CH3l. HCOOH (CH CO) OCOOH OH H2O 3 2 OH OOCCH3OHm. CH3CH2COOH SOCl2 CH CH COCl3 2 CH3CH2COOn. CH3CH(COOC2H5)21) OHCH CH COOH9.62) H+ 3) 3 2己醇A已酸BNaHCO3 水溶液水相已酸钠HCl 已酸B水相酚钠HCl 酚 C对甲苯酚C有机相已醇对甲苯酚NaOH有机相已醇A9.7 COOH COOHCOOHCOOH

44、COOHHOOC COOHHOOCCOOHCOOHCOOHHOOCH CH3 CH2(Z)易成酐(E) 不易(Z) 易成酐(E) 不易成酐9.8O O COCH3D. CH CH OHA. CH2COOHB. OC. H2C 2 2CH2COOHOH2C COCH3OCH2CH2OH精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 20 页，共 38 页第十章取代酸10.1 m. 3-氯丁酸（ 3-Chlorobutanoic acid ）n. 4-氧代戊酸（ 4oxopentanoic acid) 10.2a. CH3CH2CH2COCH2COOC

45、H3 (A) OH显色ANa2CO3溶解，有气体BCOOH CH3CHCOOHOH(B)(C)FeCl3B不显色C无变化A10.3 写出下列反应的主要产物：a. CH3COCHCOOC2H51) 稀 OH-CH3COCH2CH3CH32) H+ , H2O_ _b. CH3COCHCO2CH3CH2CO2CH3c. CH3CH2CHCOOH浓NaOH CH2COO _ + CH COO + CH OH3 3CH2COOOCOHCOOCH3d.CH3CH2OHC OO CH COCH2CH3COCH3 稀H+ C CH3 + CO2 + CH3OHOe. CH2CH2CH3COOHOCH2CH2

46、CH3+ CO2CH3f. HOOCCH2COCCOOH CH3CH3COCH(CH3)2g. CH3CH2CHCOOH Clh. CH3CHCH2COOH OHONaOH-H2OCH3CH2CHCOONaOH CH3CH=CHCOOHi.OCH3NaOH-H2O CH3CHCH2COONaCH2OHj. CH3 稀H2SO4CH3CH2CCOOHOHO CH3CH2CCH3 + HCOOH k. CH3CH2COCO2H稀H2SO4CH3CH2CHO + CO2l. CH3CHCOCO2H CH3CH3CHCOOH CH3+ CO精选学习资料 - - - - - - - - - 名师归纳总结

47、 - - - - - - -第 21 页，共 38 页O m. COOHCOOH OCOOH On. 1) NaOH,2) HCl, O OO Oo, CH3CH2COOH + Cl2PCH3CHCOOHCl10.5 完成下列转化：a. BrCH2(CH2)2CH2CO2H ONaOH O OO Ob. CO2CH3 EtOC2H5CO2CH31) 稀 OH-CH2COCH3ClCH2COCH3CH2COCH32) H+ ,c. CH3COOH OCH3CH2OH H+ CH3COOC2H5 NaOC2H5 CH3COCH2COOC2H51) OH- 1) NaOC2H52)BrCH2CH2C

48、H2BrCH3 CC COOC2H52) H+,CH3CO1) NaOC2H5CH3d. CH3COOC2H5 NaOC2H5 CH3COCH2COOC2H5COCH32) BrCH3_CH3COCHCOOC2H51) NaOC2H52) CH3CHCOOC2H5CH3CCOOOC2H5CH CHCOOC H1) 浓OH , 2) H+CH3CHCOOH CH3CHCOOH3 2 5Br精选学习资料 - - - - - - - - - 名师归纳总结 - - - - - - -第 22 页，共 38 页3 3 2 2 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

49、. 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l. (CH ) N+CH CH OHOHm. HOHOCH2CH2NH2 n. (CH3)3N+CH2CH2OCOCH3OH NHo. HO CH(OH)CH2NHCH3 p. (CH3)2CHCH2NH2q. H2N-C-NH2r. N,N- 二甲基乙胺HO11.4 HO H O H H3C H3C N H OH3C H3C N H3C H3C H N H N H H H HH C H C 3

50、 3 a 中有 三种氢键b. 中只有一种氢键11.5 如何解释下列事实？a. 因为在苄胺中， 未与苯环直接相连，其孤对电子不能与苯环共轭，所以碱性与烷基胺基本相似。b.O2NNH2中，硝基具有强的吸电子效应。-NH2 中N上孤对电子更多地偏向苯环，所以与苯胺相比,其碱性更弱。而H3CNH2中，甲基具有一定的给电子效应，使-NH2 中N上电子云密度增加，11.6 所以与苯胺相比,其碱性略强 .+_CH3CH(NH2)CH2CH3(+) 酒石酸(+) 胺(+) 酸盐物理性质不同可(-)胺(+) 酸盐拆分 ,而后再分别加NaOH 析出胺 .11.9 完成下列转化：NO2NH2a. HNO3H2SO4