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Question 47

Identify the major product A and B for the below given reaction sequence.

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Explanation: Benzene first undergoes Friedel-Crafts alkylation with isopropyl chloride in the presence of $$AlCl_3$$ to form cumene.

Cumene is oxidized by air to form cumene hydroperoxide, which on acidic hydrolysis gives phenol.

Therefore, intermediate $$P$$ is phenol.

Phenol reacts with:

$$Na_2Cr_2O_7/H_2SO_4$$

to undergo oxidation and form $$p$$-benzoquinone.

Phenol also reacts with bromine in non-polar solvent $$CS_2$$ to undergo monobromination.

Since the $$-OH$$ group is ortho/para-directing and steric hindrance favors substitution at the para position, the major product formed is $$p$$-bromophenol.

Thus, $$A = p\text{-benzoquinone}$$, $$B = p\text{-bromophenol}$$. The right option is B.

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