MHT CET 2023 Chemistry question

Identify major product A in following reaction.

3-Bromo-2-methylpentane A

(A)2-Methylpentane-3-ol
(B)2-Methylpent-2-eneCorrect
(C)4-Methylpent-3-ene
(D)4-Methylpentan-3-ol

Answer: (B)

Solution

3-Bromo-2-methylpentane is CH_3-CH(CH_3)-CHBr-CH_2-CH_3. Alcoholic KOH on heating causes dehydrohalogenation (E2 elimination), not substitution, so the alcohols in (a) and (d) are formed only by aqueous KOH. The -hydrogens are on C2 (tertiary C-H) and C4 (). By Saytzeff's rule the more

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Question ID VK-097417