Organic Chemistry

Reactions of Carboxylic Acids and Their Derivatives

R-COCl + R'COO-----> R-CO-O-COR’ + Cl-

3. Conversion to esters:

R-COCl + R'-OH --- pyridine ---> R-COOR' + Cl- + pyr-H+

4. Conversion to amides:

R-COCl + R'NHR" (excess) ---> R-CONR'R" + R'NH 2 R”Cl

R’ and/or R” may be H

5. Conversion to ketones:

Friedel-Crafts acylation

R-COCl + C 6 H 6 --- AlCl 3 ---> C 6 H 5 -COR

Reaction of Dialkylcuprates (also known as a Gilman reagent)

R-COCl + R' 2 CuLi ----> R-CO-R’

6. Conversion to aldehydes:

R-COCl + LiAlH[OC(CH 3 ) 3 ] 3 --- (1) Et 2 O (2) H 2 O ---> R-CHO

91.4.3 Acid Anhydrides

1. Conversion to acids:

(R-CO) 2 -O + H 2 O ----> 2 R-COOH

2. Conversion to esters:

(R-CO) 2 -O + R’OH ----> R-COOR’ + R-COOH

3. Conversion to amides:

(R-CO) 2 -O + H-N-(R’R”) ----> R-CON-(R’R”) + R-COOH

R’ and/or R” may be H.