Why direct halogenation of aniline is not possible?

Answer 1

Well, darling, the reason direct halogenation of aniline is a big no-no is because aniline is a strong activating group that will make the halogenation reaction go haywire and give you a messy mixture of products. Plus, the lone pair on the nitrogen atom in aniline will coordinate with the halogenating agent, making it more selective towards other positions on the ring. So, in a nutshell, direct halogenation of aniline is a recipe for disaster in the lab.

Answer 2

Direct halogenation of aniline is not possible because aniline is a meta directing group. Due to the lone pair on the nitrogen atom, the halogenation reaction occurs at the meta position on the benzene ring instead of the ortho or para positions. This makes direct halogenation of aniline inefficient and typically requires additional functional group modifications to achieve halogenation at the desired position.