Question

Which of the following orders is correct regarding basicity of indicated molecules?

• A. N, N - Dimethyltoluidine > p - toluidine > aniline > p - nitroaniline
• B. Aniline > N, N - dimethyl - p - toluidine > p - toluidine > aniline
• C. p - Toluidine > N, N - dimethyl - p - toluidine > aniline > p - nitroaniline
• D. N, N-Dimethyltoluidine > aniline > p - toluidine > p - nitroaniline

Answer 1

The correct option is A N, N - Dimethyltoluidine > p - toluidine > aniline > p - nitroaniline

Nitro group is strong electron-withdrawing group.

Hence, p - nitroaniline is least basic.

Methyl group is strong electron releasing group.

Hence, p - toluidine is more basic than aniline.

N, N - Dimethyltoluidine is more basic than p - toluidine as it contains two methyl groups on nitrogen which increase the electron density.

Hence, the order of basicity is

N, N - Dimethyltoluidine > p - toluidine >aniline > p - nitroaniline