The major product in the following conversion is –
(4-methoxyphenyl)-CH=CH-CH3 treated with HBr (excess), heat, gives ?
(4-methoxyphenyl)-CH=CH-CH3 treated with HBr (excess), heat, gives ?
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The Correct Option is D
Solution and Explanation
Step 1: HBr adds across C=C by Markovnikov addition; H goes to the far carbon so that the more stable benzylic carbocation forms, giving \(p\mathrm{-CH_3O-C_6H_4-CHBr-CH_2CH_3}\).
Step 2: With excess hot HBr, an alkyl aryl ether cleaves at the \(\mathrm{O-CH_3}\) bond (the aryl C-O bond does not break), giving the phenol and \(\mathrm{CH_3Br}\).
Product: \(p\mathrm{-HO-C_6H_4-CHBr-CH_2CH_3}\), which is option (4).
Answer: (4) p-HO-C6H4-CHBr-CH2CH3
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