Ques. 1JEE Main 2025, 29 January (Evening Shift)
Which one of the following, with HBr will give a phenol?
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Answer
(1) [figure]
Solution
HBr cleaves O-CH3 (alkyl side) of aryl alkyl ether; the aryl C–O bond never breaks.
[figure]
(2), (3), (4): oxygen is on sp³ carbons only ⇒ alkyl bromide + alcohol, no phenol.
Answer: (1)