JEE Advanced · 2019 · 27 May 2019 · Paper 1 · Alcohols Phenols and Ethers

Choose the correct option(s) for the following set of reactions

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

Answer: (B), (D)

Solution

The starting material undergoes HBr addition in presence of peroxide (anti-Markovnikov, free radical mechanism). The alkene adds HBr to give the less substituted bromide. Then

Br_{2} / h ν

causes allylic/benzylic bromination. The products shown in options (B) and (D) are consistent with these transformations: option (B) shows the anti-Markovnikov HBr adduct, and option (D) shows further bromination at an activated position.

JEE Advanced · 2019 · 27 May 2019 · Paper 1 · One or more correct options

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