Question

Arrange the following compounds in an increasing order of their property as indicated :

(i) Benzoic acid, 3,4-dinitrobenzoic acid, 4-methoxybenzoic acid (acid strength).

(ii) CH₃CH₂CH(Br)COOH, CH₃CH(Br)CH₂COOH, (CH₃)₂CHCOOH (acid strength).

Answer 1

(i) The overall acid strength increases in the order.

4-methoxybenzoic acid < benzoic acid < 3,4-dinitrobenzoic acid.

(ii) We know that +I-effect decreases while –I-effect increases the acid strength of carboxylic acids. The overall acid strength increases in the order. (CH₃)₂CHCOOH < CH₃CH(Br)CH₂COOH < CH₃CH₂CH(Br)COOH