JEE Main Chemistry question

In the reaction sequence: (I) 3-methylbutan-2-ol, H⁺/heat → A (major) + B (minor); (II) A, HBr (dark, no peroxide) → C (major) + D (minor); the major products (A) and (C) are respectively

(A)Rearranged, more-substituted alkene, and the corresponding Markovnikov bromideCorrect
(B)Unrearranged alkene and its anti-Markovnikov bromide
(C)A diene and a dibromide
(D)None of these

Answer: (A)

Solution

Acid-catalysed dehydration of a secondary alcohol adjacent to a more substituted carbon proceeds through the initial secondary carbocation, which undergoes a hydride/methyl shift to the more stable tertiary carbocation

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Question ID VK-139918