JEE Main Chemistry question

3-Methylbutan-2-ol, on treatment with HCl, predominantly gives

(A)2-Chloro-2-methylbutaneCorrect
(B)2-Chloro-3-methylbutane
(C)2,2-Dimethylpropane
(D)None of these

Answer: (A)

Solution

Protonation and loss of water from this secondary alcohol initially gives a secondary carbocation, which rapidly rearranges via a 1,2-hydride shift to the more stable tertiary carbocation;

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Question ID VK-148890