JEE Main Chemistry question

The major product formed when a 3,3-dimethyl butan-2-ol is heated with concentrated sulphuric acid, is [GUJ CET 2008]

(A)2,3-dimethyl-2-buteneCorrect
(B)2,3-dimethyl-1-butene
(C)3,3-dimethyl-1-butene
(D)*cis* and *trans* isomers of 2,3-dimethyl-1-butene

Answer: (A)

Solution

Acid-catalysed dehydration of 3,3-dimethylbutan-2-ol [(CH)C–CH(OH)–CH] proceeds through a secondary carbocation that undergoes a 1,2-methyl shift to the more stable tertiary carbocation, (CH)C–CH(CH)-type

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Question ID VK-142128