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Why can aniline not be brominated directly to 4-bromoaniline?

Why can aniline not be brominated directly to 4-bromoaniline?
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Answer #1

The addition of Bromine to aniline is a electrophilic aromatic substitution. Since it is an electrophilic substitution reaction it attacks the positions where the electron concentration is very high.

As you can see form the picture above, the resonance structure of aniline, is electron rich at ortho and para but not at meta postions. So Bromination of Aniline directly is not possible since ortho and para are the major products formed instead of meta.

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