JEE Main · 2019 · 09 Apr 2019 · Shift 2 · Alcohols Phenols and Ethers

p -Hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives:

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

p-Hydroxybenzophenone has two rings: one activated by the electron-donating

- OH

and one deactivated by the electron-withdrawing carbonyl. In the non-polar solvent

CCl X_{4}

, with no Lewis-acid catalyst present, bromine carries out only a mild electrophilic substitution and goes onto the activated, phenol-bearing ring. The

- OH

directs ortho and para, but the para position is already taken by the benzoyl group, so the bromine enters ortho to the

- OH

, giving the ortho-brominated hydroxybenzophenone.

JEE Main · 2019 · 09 Apr 2019 · Shift 2 · Single correct option

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