二、a-卤代反应 例题与习题 完成下列反应 Cl2(1 mol) CH3 CCH CH3 CHCCH3 H2O, HOAc C 12( excess) CH3 CH2 CHCH3 NaoH CH3CH2CH2 COOH CHI OH Br. 2( excess (CH3)3CCCH3 (CH3)3CCOOH CHBr3 Naoh Br2(2 mol) CH2 CH3 Br CH2CH3 NaoH Br
二、α – 卤代反应 例题与习题 完成下列反应 CH3CH2CCH3 O H2O, HOAc CH3CH2CH2CHCH3 OH I2 ( excess) NaOH (CH3)3CCCH3 O Br2 ( excess) NaOH O CH2CH3 Br2 ( 2 mol ) NaOH Cl2 ( 1 mol ) CH3CHCCH3 O Cl CH3CH2CH2COOH + CHI3 (CH3)3CCOOH + CHBr3 O CH2CH3 Br Br
二、a-卤代反应 (2)羧酸及酰卤 Hell-Volhard-Zelinski reaction (HVZ reaction) O 1. PBr3(or P), Br RCHoCOH 2.H2O '>RCHCOh Br mechanism for the hell-Vothard-Zelinski reaction OH CH3 CH2-C--Ou PB13, CH3CH2-C--Br CH3CH=C—Br a carboxylic acid an acyl bromide enol Br一Br 0: OH CH3CH-C-OH H2O CH2 CH-C-Br CH3CH-C—Br+Br Br B1 B an a-brominated an a-brominated carboxylic acid acyl bromide
二、 α – 卤代反应 (2) 羧酸及酰卤 Hell-Volhard-Zelinski reaction (HVZ reaction)
二、a-卤代反应 例题与习题 完成下列反应 EtOH COCI COoT PBI (CH3)2 CHCH2COOH (CH3),,COBr EtOH (CH3)2CHCH2COoEt Br2( CH3)CHCHCOOH EtOH(CH3)CHCHCOOEt ( CH3)CHCH2 COOH P(cat. Br Br
二、α – 卤代反应 例题与习题 完成下列反应 COOH SOCl2 (CH3)2CHCH2COOH PBr3 (CH3)CHCH2COOH Br2 P(cat.) EtOH EtOH H+ EtOH COCl (CH3)2CHCH2COBr (CH3)CHCHCOOH Br COOEt (CH3)2CHCH2COOEt (CH3)CHCHCOOEt Br
Ado加成和Ado缩合 1. Aldol addition and aldol condensation RCHCR RCH2CR a nucleophile lan electrophile Aldol addition B-hy droxyaldehyde B-hydroxyketone Aldol condensation( a, B-unsaturated aldehyde I as B-unsaturated ketone
三、Aldol加成和Aldol缩合 1. Aldol addition and aldol condensation RCHCR RCH2CR O O a nucleophile an electrophile Aldol addition Aldol condensation β-hydroxyaldehyde β-hydroxyketone α, β -unsaturated aldehyde α, β -unsaturated ketone
Ado加成和Ado缩合 1. Aldol addition and aldol condensation aldol additions OH HO 2 CH2CHCH CH2CHCH—CHCH CH a B-hydroxyaldehyde oH O HO 2 CH3CCH 3 CH3C一CH2CCH3 CH aβ- hydroxyketone
三、Aldol加成和Aldol缩合 1. Aldol addition and aldol condensation