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Amines

Question
CBSEENCH12009130

Why does bromination of aniline, even under very mild conditions give 2, 4, 6- tribromo aniline instantaneously?

Solution
This high reactivity of aniline is due to the fact that, in addition to other resonating structures that stabilizes the intermediate carbonium ion in aromatic electrophilic substitution, the following two structures are also formed due to the interaction of nitrogen lone pair of an electron with the positively charged ring. This also contributes to the stability of the intermediate in o, p-bromination.