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Question 57

The correct order of basicity is

Aliphatic amines are more basic than aromatic amines because the lone pair in aromatic amines is delocalized into the benzene ring via resonance.

$$p$$-methoxyaniline: The methoxy group ($$-OCH_3$$) exert a strong $$+M$$ (Mesomeric) effect. This highly increases basicity relative to aniline.

Aniline: It has no additional substituents. The lone pair is delocalized into the ring, making it less basic than aliphatic amines but more basic than those with withdrawing groups.

$$p$$-nitroaniline: The nitro group ($$-NO_2$$) is a powerful $$-M$$ and $$-I$$ group. This highly decreases basicity.

Thus, the increasing order of basicity is $$p\text{-nitroaniline} < \text{Aniline} < p\text{-methoxyaniline} < CH_3NH_2$$

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