The major product(P) in the following reaction is [figure]
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Answer
(3) [figure]
Solution
Excess HBr reacts at both groups:
1. Ether: Ar-O-C2H5 + HBr Ar-OH + C2H5Br
∵ Ar–O bond has partial double-bond character (resonance), so Br- attacks the ethyl carbon; the phenol –OH is not replaced by Br.
2. Vinyl group (Markovnikov, via the more stable benzylic carbocation):
Ar-CH=CH2 + H+ Ar- CH-CH3
Ar- CH-CH3 + Br- Ar-CHBr-CH3
[figure]
Answer: (3)