H2O - C-OH HCI C-CI 2NH3 Pyridine(Pyr.)吡啶 C-CI +C2H5OH C-OC2H5 HCI NaOH溶液 C-O 或P
e.g. C Cl O + H2O C OH O + HCl C Cl O + 2NH3 C NH2 O + NH4Cl C Cl O + C2H5OH Pyridine (Pyr.) 吡啶 C OC2H5 O + HCl C Cl O + HO NaOH溶液 或Pyr. C O O + HCl
CH3CO)20 +H2O 2 CH3CO2H CH3CO)20+ 2NH 无法显示该图片 H2C-C CH2-CONH2 H+ CH2-CONH2 o+ 2NH3 H2C-C CH2-CO2 NH4 CH2-CO2H (CH3 CO)20+ CH3OH CH3 COOCH3 H3CCO2H o|cco CH C-o+ H3CCH2CHCH COOCHCH2CH3 H
2CH3CO2H H2C C H2C C O O O + 2NH3 CH2 CH2 CONH2 CO2NH4 H + CH2 CH2 CONH2 CO2H CH3COOCH3 + H3CCO2H C C O O O + H3CCH2CHCH3 OH COOCHCH2CH3 CH3 COOH (CH3CO)2O + 2NH3 (CH3CO)2O + H2O (CH3CO)2O + CH3OH
b.酯的反应 RCOOR+H2O RcOH ROH 水解 HO RCO, Na rOh 碱水解 HO+R—C—OR R—C-OH R-C—OH+ RO-RCOO+ROH OR 酸水解 O H OH OH R—C-OR'+ OR' HOH R—C-OR R—C-R OH2 H OH ROH 影响水解速度的因素 RCOH R-C-OH+
b. 酯的反应 RCOOR' + H2O H + HO - RCO2H + R'OH RCO2 - Na + + R'OH 水解 R C O HO OR' - + C O - OR' R OH R C O OH R'O - RCOO - + + R'OH R C O OR' + H + R C O OR' H + HOH R C OH OR' OH2 R C OH OR' OH H + R C OH OH + + - R'OH R C O OH H + 碱水解 酸水解 影响水解速度的因素
酯水解的部位及产物的立体化学 R—C3O—CHRR R--C--0--CRR"R 酰氧键断裂 烷氧键断裂 立体化学: 保持 消旋化 问题? H3O 8 RCOOC RRR Rcooh RRR"COH (部分外消旋) H3O RCOOC HRR RCOO°H+RR"HCOH (构型保持)
酯水解的部位及产物的立体化学 R C O CHR'R'' O * R C O CR'R''R''' O * 酰氧键断裂 烷氧键断裂 立体化学： 保持 消旋化 RCOOC*R'R''R''' + H3O 18 RCOOH + R'R''R'''CO 18 H 3 o - （部分外消旋） RCOOC*HR'R'' + H3O 18 RCOO 18 H + R'R''HCOH 2 o - （构型保持） 问题 ？
RCOOR+ NH3 >RCONH2+ C2HsOh 氨解 RCOOR+R"OH酸, RCOOR"+ROH酯交换 H COC2H5 CH3CO2 C2H5 NH3 HO RCOOCH RCO,CH CH-OH R'COOCH+ CH3OH Acid or Base R'COCH CH2-Oh R"COOCH2 CH2-OH R"CO2 CH3
RCOOR' + NH3 RCONH2 + C2H5OH 氨解 RCOOR' + R''OH 酸或碱 RCOOR'' + R'OH 酯交换 H + HO - COC2H5 O CH3CO2C2H5 + NH3 RCO2CH3 R'CO2CH3 R''CO2CH3 + CH2 CH2 CH2 OH OH OH RCOOCH2 R'COOCH R''COOCH2 + CH3OH Acid or Base