Organic Chemistry

Unit 13:Carboxylic acid derivatives

4. Conversion to aryl ketones (Friedel-Crafts acylation):

(R-CO) 2 -O + C 6 H 6 --- AlCl 3 C 6 H 5 -COR + R-COOH

91.4.4 Esters

1. Hydrolysis:

R-COOR' + H 2 O <--- HA ---> R-COOH + R’-OH

R-COOR’ + OH- ----> RCOO-+ R’-OH

2. Transesterification (conversion to other esters):

R-COOR' + R"-OH <--- HA ---> R-COO-R" + R'-OH

3. Conversion to amides:

R-COOR' + HN-(R"R"') ----> R-CON-(R"R"') + R'-OH

R” and/or R”’ may be H

4. Reaction with Grignard reagents:

R-COOR' + 2 R"MgX --- Et 2 O ---> R-C-R” 2 OMgX + R’OMgX ---> H 3 O+

R-C-R” 2 OH

The intermediate and final product is a tetrahedral carbon with two R” attached directly
to the carbon along with R and OH/OMgX

X = halogen.

5. Reduction:

R-COOR' + LiAlH 4 --- (1) Et 2 O (2) H 2 O ---> R-CH 2 OH + R’-OH

91.4.5 Amides

1. Hydrolysis:

R-CON(R'R") + H 3 O+ --- H 2 O ---> R-COOH + R’-N+H 2 R”

R-CON(R’R”) + OH- --- H 2 O ---> R-COO- + R’-NHR”

R,R’ and/or R” may be H.