厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十章 羧酸 Carboxylic Acids 10.6 卤代酸 Halo Acids

106卤代酸 Halo acids

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.6 卤代酸 Halo Acids

10.6.1卤代酸的制备 Preparation of halo acids a-卤代酸的制备(见羧酸的-卤代) B卤代酸的制备 R-CH=CHCO,H HBr Br

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.6.1 卤 代酸的制 备 Preparation of halo acids „ α-卤代酸的制备 (见羧酸的 α-卤代 ) „ β-卤代酸的制备 R CH CHCO 2 H + HBr R C H C H 2CO 2 H Br

10.62卤代酸的反应 Reaction of halo acids Naoh H、 RCHCO2H HO OH RCHCODH NH 3 RCHCO2H Br NH (1)NaHcO H3o RCHCO2H RCHCO,H (2)NaCn CN COH

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.6.2 卤 代酸的反应 Reaction of halo acids RCHCO 2 H Br RCHCO 2 H OH RCHCO 2 H NH 2 RCHCO 2 H CN NaOH H 2 O NH 3 H + (1)NaH C O 3 (2) N a C N H 3 O + RCHCO 2 H CO 2 H

NaoH-hoo RCHCHCOH RCH=CHCO,Na Br H RCHECHCOH CH3 Naoh O H3C-C-CO2H H2C-C—C CC CHoIr CHo-O CH NaoH-H.o H3C-C-CO,Na CHOH

Organic Chemistry Organic Chemistry Xiamen Xiamen University University RC H C H 2CO 2 H Br NaOH￾H 2 O RCH CHCO 2Na H + RC H CHCO 2 H H 3C C CH 2Br CH 3 CO 2 H Na O H CCl 4 H 3C C CH 2 CH 3 C O O NaOH￾H 2 O H 3C C CH 2OH CH 3 CO 2Na

Mechanism CH3 O CH Naoh O OH H2C-C-C H3C-C—C CH 0- CCl4 CH2-0 Br Ch2 oh CH CH3 HC-CC0一H3C-C-CO2H一→HC-C-CO2 ①D CH -o CH,O CH,OH ⑨D

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Mechanism Mechanism H 3C C CH 2 CH 3 C NaOH CC l 4 H 3C C CH 2 CH 3 C O O H 3C C CH 2 O CH 3 CO 2 H O O Br OH H 3C C CH 2 CH 3 C O O OH H 3C C CH 2OH CH 3 CO 2

Na, cO CI(CH2)3C-OH H2O C(CH2)3C-0 NaoH HO(CH23C-O OtO H2O H

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Cl(C H 2 ) 3C O H O Na 2CO 3 H 2 O Cl(C H 2 ) 3C O O O O NaOH H + H 2 O H O(C H 2 ) 3 C O O

Naoh CI(CH2)4C-OH CI(CH2)4C-O H2O NaoH HO(CH2)4C-0 H2O OO

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Cl(C H 2 ) 4C O H O NaOH H 2 O Cl(C H 2 ) 4C O O O O NaOH H 2 O H O(C H 2 ) 4 C O O

10.7羟基酸 Hydroxy acids

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.7 羟基酸 Hydroxy acids

10.71羟基酸的制备 Preparation of hydroxy acids c羟基酸的制备 (1)由卤代酸制备 ③(2)由醛、酮与HCN加成后水解 β羟基酸的制备 l)羟醛缩 (2)∝卤代醇与NaCN取代后水解

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 10.7.1 羟 基酸的制 备 Preparation of hydroxy acids α- 羟 基酸的制 备 (1) 由 α-卤代酸制备 (2)由醛 酮与HCN加成后水解 β- 羟 基酸的制 备 (1) 羟醛缩合 (2) α-卤代醇与NaCN取代后水解

9-羟基酸的制备 引由Q卤代酸水解 02C OoC 浓OH C—Br H0---C----Br S H/ CH CH CO Ho- t Br CH

Organic Chemistry Organic Chemistry Xiamen Xiamen University University α−羟基酸的制备 由 α-卤代酸 水 解 C Br O 2 C CH 3 H 浓OH C Br O 2 C CH 3 H HO C CO 2 CH 3 H HO + Br