Question

Which one of the following, with HBr will give a phenol?

• A. A benzene ring is connected to a carbon atom bonded to two methoxy groups (OCH3) and a hydrogen atom. A methylene group (CH2) connects the benzene ring to the central carbon.
• B. A benzene ring is connected to an oxygen atom, which is connected to a carbon atom bonded to three methyl groups (CH3). A methylene group (CH2) connects the benzene ring to the oxygen atom.
• C. A benzene ring is connected to a methoxy group (OCH3).
• D. A benzene ring is connected to a methoxy group (OCH3) via a methylene group (CH2).

Answer 1

Answer: (C)

Option (C)

Answer 2

Explanation: Anisole (structure C) has the –OCH₃ group directly attached to the benzene ring. When treated with HBr, the methyl group is cleaved off by nucleophilic substitution, yielding phenol and methyl bromide.