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Question 53

The major product in the following reaction 

The benzylic $$-OH$$ group is protonated and leaves as $$H_2O$$ to form a stable benzylic carbocation, which is then attacked by $$Cl^-$$ to form a $$-CH_2Cl$$ group.

The $$-OH$$ group directly attached to the benzene ring does not react because the $$C-O$$ bond has partial double-bond character due to resonance, making it difficult to break.

The major product is p-hydroxybenzyl chloride, as shown in Option D.

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