Arrange the following compounds in increasing order of their basicity
(A) Aniline
(B) p-Nitroaniline
(C) p-Toluidine
(D) p-Methoxyaniline
Choose the correct answer from the options given below:
Answer & explanation
Correct answer: option 3
The correct answer is Option (3) → (B), (A), (C), (D)
Basicity of anilines depends on the electron-donating or withdrawing nature of the substituent:
- p-Nitroaniline (NO₂) → strong electron-withdrawing, decreases basicity (least basic)
- Aniline → baseline
- p-Toluidine (CH₃) → weak electron-donating, increases basicity
- p-Methoxyaniline (OCH₃) → strong electron-donating, most basic
Increasing order of basicity:
p-Nitroaniline < Aniline < p-Toluidine < p-Methoxyaniline
i.e. (B) < (A) < (C) < (D)