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Question 53

The major product of the following reaction is:

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  1. Electrophilic Aromatic Substitution:

    The hydroxyl group ($$-\text{OH}$$) is a powerful activating group that directs incoming electrophiles to its ortho and para positions. Both positions ortho to the $$-\text{OH}$$ group are open and readily undergo bromination.


  2. Ipso-Bromodebenzylation (Ipso-Substitution):

    The para position is already occupied by a sulfonic acid group ($$-\text{SO}_3\text{H}$$). Because the sulfonic acid group is an excellent leaving group, a third bromine electrophile attacks this occupied position (ipso-attack), displacing the sulfur trioxide ($$-\text{SO}_3$$) group.

Conclusion:

The combined ortho-bromination and para-desulfonation results in the complete conversion of the substrate into a symmetrically trisubstituted phenol.

Answer: Option A — 2,4,6-Tribromophenol

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