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 CH2COOH3. (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)