Organic Chemistry

Unit 13:Carboxylic acid derivatives

91.4 Reactions of Carboxylic Acids and Their Derivatives

91.4.1 Carboxylic Acids

1. As acids:

RCO 2 H + NaOH ----> RCO 2 - Na++ H 2 O

RCO 2 H + NaHCO 3 ----> RCO 2 - Na++ H 2 O + CO 2

2. Reduction:

RCO 2 H + LiAlH 4 --- (1) Et 2 O -- (2) H 2 O ----> RCH 2 OH

2a) Fukyama reduction: Pd and Et3SiH COOH->CHO

3. Conversion to acyl chlorides:

RCO 2 H -----SOCl 2 or PCl 5 ----> RCOCl

4. Conversion to esters (Fischer esterfication):

RCOOH + R'-OH <--- HA ---> RCOOR' + H 2 O

5. Conversion to amides:

RCO 2 H -----SOCl 2 or PCl 5 ----> RCOCl + NH 3 <------> RCOO-NH 4 + ---

heat ---> R-CONH 2 + H 2 O

6. Decarboxylation: (Note: you need a doubly-bonded oxygen (carbonyl) two carbons
   away for this reaction to work)

RCOCH 2 COOH --- heat ---> R-COCH 3 + CO 2

HOCOCH 2 COOH --- heat ---> CH 3 COOH + CO 2

91.4.2 Acyl Chlorides

1. Conversion to acids:

R-COCl + H 2 O ----> R-COOH + HCl

2. Conversion to anhydrides: