第七章炔烃和二烯烃 1.写出下列反应的产物 2.下列化合物可由什么原料合成? C≡N H HaC CH3 CO2CH3 CO2CH3 3.从指定原料合成下列化合物: (1)环己烯 乙氧基环己烷 (2)丙炔—1-丁烯 (3)环己烯—-丙基环己烷 (4)1-己炔 1,4-王二烯 (5)乙炔及其他原料—-(-6-十三碳烯(雌性苍蝇的性诱引素) 4.一旋光化合物CsH12(A),用铂催化剂加氢得到没有手性的化合物CsHs(B,(A)用 Lindlar 催化剂加氢得到手性化合物CsH14C,但用金属钠在液氨中还原得到另一个没有手性的化合 物CsH14D)试推测(A),(B,(C),(D)的结构 5.用系统命名法命名下列化合物 (I)(CH3)3CC=CCH2 CH3 (2)D-C C≡CH (3)HC≡cCH2Br (4)CH2=CH-c≡CH(5)H3C-CH=CH-C≡CH(6)HC≡C-C=cH2 CH3 CH2 CH3 CH2C≡CH (9)(CH3)C=CHCH=CHCH3
第七章 炔烃和二烯烃 1. 写出下列反应的产物. 2. 下列化合物可由什么原料合成? (1) (2) (3) (4) C C N N H CN H3C O CH3 CO2CH3 H CO2CH3 3C O O O 3. 从指定原料合成下列化合物: (1) 环己烯 乙氧基环己烷 (2) 丙炔 1-丁烯 (3) 环己烯 丙基环己烷 (4) 1-己炔 1,4-壬二烯 (5) 乙炔及其他原料 (Z)-6-十三碳烯(雌性苍蝇的性诱引素) 4. 一旋光化合物 C8H12(A),用铂催化剂加氢得到没有手性的化合物 C8H18(B),(A)用 Lindlar 催化剂加氢得到手性化合物 C8H14(C),但用金属钠在液氨中还原得到另一个没有手性的化合 物 C8H14(D).试推测(A), (B), (C), (D)的结构. 5. 用系统命名法命名下列化合物: (1) (CH3 )3CC CCH2CH3 (2) C CH (3) HC CCH2Br (4) CH2=CH C CH (5) H3C CH=CH C CH (6) HC C C CH3 CH2 (7) CH2CH3 CH2C CH (8) H H CH3 CH3 (9) (CH3 )2C=CHCH=CHCH3
(10)PhCH-CHCH-CH2 (ID(( 6.判断2戊炔与下列试剂有无反应如有反应,写出主要产物的结构式 (1)Br2(Imol) (2)HCl(Imol) (3)H3O (4) AgNO3, NH4OH (5) CH3 CH2 MgBr, ET20 (6)1)B2H6;2)H2O2,OH (7)H2/Lindlar Pd (8)Na+NH() (9)热的KmnO4溶液 (10)aq. NaCI 7.写出下列反应主要产物 (1)CH2C≡C—CH=cHcH3 /Lindlar pd (2)CH3C≡CCH2CH2CH3 Na+ NH3O NaNh CH3 CH,MgBr (3)CH3CH2C≡CH CH3 CH,Mgh CHI (4)CH3CH2C≡CH Br、Br 1)NaNH,, NH3 Ph Ch,CH 2)H30 8.用化学方法区别下列各组化合物 (1)CH3CH2C=CCH3 CH3(CH2)3CECH CH3CH=CHCH=CH2 (2)CH, CH,,CI (CH3)3CCl CHCH=CHCI (3)CH3(CH2)4CH3 CH3(CH2)3C=CH CH3(CH2)3 CH=CH 答案(1-8) CO2Et CO2CH H H3CO2C CO2 CH3 CO2 CH CN (2) 人 H3CO2C、CO2CH H3C CH
(10) PhCH=CHCH=CH2 (11) (12) Cl Cl 6. 判断 2-戊炔与下列试剂有无反应,如有反应,写出主要产物的结构式. (1) Br2 (1mol) (2) HCl (1mol) (3) H3O+ (4) AgNO3, NH4OH (5) CH3CH2MgBr, ET2O (6) 1) B2H6; 2)H2O2,OH- (7) H2/Lindlar Pd (8) Na + NH3(l) (9) 热的 KmnO4 溶液 (10) aq. NaCl 7. 写出下列反应主要产物: (1) CH3C C CH=CHCH3 H2 /Lindlar Pd (2) CH3C CCH2CH2CH3 Na + NH3 (l) (3) CH3CH2C CH NaNH2 CH3CH2MgBr (4) CH3CH2C CH CH3CH2MgBr CH3 I (5) Br Ph CH2CH3 Br 1) NaNH2 , NH3 2) H3O + 8. 用化学方法区别下列各组化合物: (1) (2) (3) CH3CH2C CCH3 CH3 (CH2 )3C CH CH3CH=CHCH=CH2 CH3CH2CH2Cl (CH3 )3CCl CH3CH=CHCl CH3 (CH2 )4CH3 CH3 (CH2 )3C CH CH3 (CH2 )3CH=CH2 答案(1-8): 1. (1) CO2Et CO2Et (2) CO2CH3 CO2CH3 (3) H CO2CH3 H3CO2C H + (4) CO2CH3 2. (1) CN CN + (2) CN + (3) H3C O CH3 H3CO2C CO2CH3 + (4) O O O +
iH2SO4, HO il) NaoH, CH3 CH2Br or i) Hg(OAc), EtOH 1) NabH4 (2)CHcC≡cH-NaCH3C≡CNa H3I CH3C CCH Lindlar Pd. CH, CH=CHCH3-HB-- CH CH2 CH(Br)CH, KOC(CH3)3, HOC(CH) TM △ Br CHICH,CHhCuL CH2CH2CH (4) 1)NaNH2 1i) CH2-CHCH2 CI ii) H2, Lindlar Pd (5) 1)NaNH2 ii) CH3CH2CH2CI iii) NaNH2 Iv)CH3(CH2)CHCI v)H,, Lindlar Pd (A): H3C-C=C-L (B): CH3(CH2)CH(CH3)CH2CH2 CH3 CH3 CH3 (D) H3C CI H3C 5.(1)2,2-二甲基-3-己炔 (2)环丙基乙炔 (3)3-溴-1-炔 (4)1-丁烯-3-炔 (5)3-戊烯--炔 (6)2-甲基-1-丁烯3-炔 (7)1-乙基-2-炔丙基环己烯 8)(E,E)-24-己二烯 (9)2-甲基-2,4-己二烯 (10)1-苯基-1,3-丁二烯 (12)2,3-二氯二环[22.1庚-2-烯 (1)Br CH2CH (2)H CH2CH3 H3C (4) CH3CH._ CH3 (5) (6)O CH3CCH2CH2CH3 (7)H3C、 CH2CH3 CH2CH (9)HCOOH (10 CH3 CH2COOH
3. (1) i) H2SO4 , H2O ii) NaOH, CH3CH2Br or i) Hg(OAc)2 , EtOH ii) NaBH4 (2) CH3C CH NaNH2 CH3C CNa CH3C CCH3 CH3 I H2 /Lindlar Pd CH3CH=CHCH3 HBr CH3CH2CH(Br)CH3 KOC(CH3 )3 , HOC(CH2 )3 TM (3) Br CH2CH2CH3 HBr (CH3CH2CH2 )2CuLi (4) i) NaNH2 ii) CH2=CHCH2Cl iii) H2 , Lindlar Pd (5) i) NaNH2 ii) CH3CH2CH2Cl iii) NaNH2 iv) CH3 (CH2 )6CH2Cl v) H2 , Lindlar Pd 4. (A): H3C C C H C CH3 CH3 (B): CH3 (CH2 )2CH(CH3 )CH2CH2CH3 (C): H3C CH CH3 CH3 (D): H3C CH CH3 CH3 5. (1) 2,2-二甲基-3-己炔 (2) 环丙基乙炔 (3) 3-溴-1-炔 (4) 1-丁烯-3-炔 (5) 3-戊烯-1-炔 (6) 2-甲基-1-丁烯-3-炔 (7) 1-乙基-2-炔丙基环己烯 (8) (E, E)-2,4-己二烯 (9) 2-甲基-2,4-己二烯 (10) 1-苯基-1,3-丁二烯 (11) 苯乙烯 (12) 2,3-二氯二环[2.2.1]庚-2-烯 6. (1) Br C H3C C CH2CH3 Br (2) H C H3C C CH2CH3 Cl (3) CH3CH2CCH2CH3 O (4) (5) (6) CH3CCH2CH2CH3 O (7) H3C H CH2CH3 H (8) H H3C CH2CH3 H (9) HCOOH, CH3CH2COOH (10)
7 (2)H3C、 CH2CH2 CH3 (3)CHCH2C≡CNa (4)CH2CH2C≡ CMgBr CH3CH2C≡ccHz2CH3 CH3CH2C≡CCH3 PhCH2ECH (1) 1)AgNO3, NH3, H2O (2) i)AgNO3, EtOH 11) Nal-CH3 COCH3 (3) 1)AgNO3, NH3, H2O 11) Br2, CCl4
7. (1) (2) H3CH HCH2CH2CH3 (3) CH3CH2C CNa , CH3CH2C CCH2CH3 (4) CH3CH2C CMgBr , CH3CH2C CCH3 (5) PhCH2C CH 8. (1) (2) (3) O OO i) AgNO3, NH3,H2O ii) i) AgNO3, EtOH ii) NaI-CH3COCH3 i) AgNO3, NH3,H2O ii) Br2, CCl4