A. Phenyl methanamine
B. N, N-Dimethylaniline
C. N-Methyl aniline
D. Benzenamine
Choose the correct order of basic nature of the above amines.

Let us first identify each amine:

A. Phenyl methanamine is $$C_6H_5CH_2NH_2$$ — benzylamine, an aliphatic primary amine (the $$-NH_2$$ group is on the $$-CH_2-$$ carbon, not directly on the ring).

B. N,N-Dimethylaniline is $$C_6H_5N(CH_3)_2$$ — a tertiary aromatic amine.

C. N-Methylaniline is $$C_6H_5NHCH_3$$ — a secondary aromatic amine.

D. Benzenamine is $$C_6H_5NH_2$$ — aniline, a primary aromatic amine.

Benzylamine (A) is an aliphatic amine because the nitrogen lone pair is not involved in resonance with the benzene ring. In aromatic amines (B, C, D), the lone pair on nitrogen delocalizes into the ring, reducing basicity. Therefore, benzylamine is the most basic of all four.

Among the aromatic amines, methyl groups on nitrogen donate electron density through their inductive effect (+I effect), which partially compensates for the resonance withdrawal. N,N-Dimethylaniline (B) has two methyl groups on nitrogen, making it more basic than N-Methylaniline (C), which has one methyl group. Aniline (D) has no methyl groups on nitrogen and is the least basic.

Therefore, the order of basic nature is: $$A > B > C > D$$.