135写出下列反应的机理。 (1)CHCH-CH-CHOH+HCI ZnC-CH CH-CH.CH-CI )(CH)COH+HCI ZnC(CH)C-CI (3)(CH3)3CCHCH3 +HC →(CH3)2CCH(CH32 OH ④〈◇-CCH2+HBr →CH OH CH3 Br ⑤(CHC-C(CH Ag(CH,CCCH OH 0 OHOH (6) -C-CH3→CH CH3 (7)(CH3)3COCH3+HBr →(CH3)CBr+CH,OH (8)(CH3)C-CH2+CHOHH(CH)C-CH2OH 0 OCH3 (CHa)C-CH2+CHOH CHONa-(CHC-CH2OCHs o (10) GCH-CH.CI CHO →CH2一CH-CHz-OCH 13.6完成下列反应。 (CH3)3CCHCH3 HBr? OH CH2CH2OH (2) OH CH3 S0C2→？ (3) C--H C2HS OH 1s0C2→2 吡 KMnO4.H2O-2 -CH2OH- CHO13.5 ￾✂✁✻☛✝☞✡✏✍✒✔✓✻✐✝❥✔✚ . (1) CH3CH2CH2CH2OH + HCl CH3CH2CH2CH2Cl ZnCl2 (2) (CH3 )3COH + HCl (CH3 )3C Cl ZnCl2 (3) (CH3 )3CCHCH3 + HCl OH (CH3 )2CCH(CH3 )2 Cl (4) C(CH3 )2 + HBr OH CH3 CH3 Br (5) (CH3)2C OH C(CH3)2 (CH3 )3CCCH3 O Ag (6) OH C CH3 OH CH3 CH3 C O H + + CH3 CH3 O (7) (CH3 )3COCH3 + HBr (CH3 )3CBr + CH3OH (9) (CH3 )2C CH2 + CH3OH O (CH3 )2C OCH3 (8) (CH3 )2C CH2 + CH3OH CH2OH O (CH3 )2C OH CH2OCH3 CH3ONa (10) CH2 CH CH2Cl O CH2 CH CH2 O OCH3 CH3O 14 - 14 13.6 ❦✝❧☛✝☞✡✏✍✒❆✚ (1) (CH3 )3CCHCH3 OH ? HBr (2) CH2CH2OH OH ? ? HBr NaOH (3) CH2OH ? ? KMnO4 ,H2O CHO C CH3 H C2H5 OH

SOCl2 SOCl2 (4)