Cyclopentylmethanol (a cyclopentane ring bearing a -CH_2OH group) is treated with H_2SO_4. The major product is

JEE Main Chemistry question

Cyclopentylmethanol (a cyclopentane ring bearing a group) is treated with . The major product is

(A)A six-membered ring bearing an exocyclic group
(B)A six-membered ring bearing a ring methyl substituent and an exocyclic group
(C)Cyclohexene (an unsubstituted six-membered ring alkene)Correct
(D)A six-membered ring bearing an ethyl substituent and a double bond

Answer: (C)

Solution

Protonation and loss of water from the primary alcohol would give an unstable primary carbocation on the exocyclic carbon; instead, a ring C–C bond migrates (1,2-alkyl shift), expanding the five-membered ring to a

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Question ID VK-148694