JEE Main 2006 Chemistry question

Reaction of trans-2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces

(1)4-phenylcyclopentene
(2)2-phenylcyclopentene
(3)1-phenylcyclopentene
(4)3-phenylcyclopenteneCorrect

Answer: (4)

Solution

E2 needs an anti-periplanar (trans-diaxial) β-H. In the trans isomer, the H on C-2 (bearing Ph) is cis to Br, so it cannot be eliminated; the anti H on C-5 is

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Question ID VK-038839