Question

why aniline is less basic than methyl amine​

Answer 1

Explanation:

The reason given for the question is that in aniline the lone pair on N atom is delocalized throughout the benzene ring, making it less available for donation.

But the conjugate acid of aniline should be more stable given the fact that the positive charge on N atom is also delocalized throughout the ring, hence making it more stable than the conjugate acid of methylamine which has +I effect. On that account, shouldn't aniline be more basic?

Answer 2

Answer:

Because, the unpaired electrons which is the lone pair of nitrogen atom gets in conjugation with the 6π electrons of benzene ring due to resonance. And, hence because there is resonance the lone pair have got in conjugation and thus they cannot easily donate lone pair to act as Lewis Bases.

However, there is no such conjugation In methyl amine and hence methyl amine is much better base than aniline.

Hope this helps you !