Question

Write an equation for all 3 aromatic compounds (acetanilide, aniline, and anisole) yielding a monobrominated reaction product at the para position.

Answer 1

The reactions we can see in diagram are all Aromatic Electrophilic Substitution Reaction or more particularly they are Aromatic Electrophilic Bromination Reactions. Br2 can be polarized more and made to give potential bromonium ion (Br⁺⁾ by using polar protic solvent like acetic acid.

I) The reaction of bromination will be very effective with aniline compound as lone pair is well conjugated in benzene ring and activated o/p position effectively.

II) Secondly effective aromatic system will be anisole which has O with lone pare available readily for conjugation in benzene ring and activating o/p position effectively

III) Acetanilide is least reactive among these, as lone pair of N is involved in conjugation with C=O bond and less readily available for conjugation in benzene ring to activate the ring towards bromination.