JEE Main Chemistry question

ChemistryAlcohols, Phenols and EthersJEE Main

A number is assigned to each of the following alcohols: (1) 1-phenylbutan-1-ol (2) 1-phenylbutan-2-ol (3) 2-phenylbutan-1-ol (4) 2-phenylbutan-2-ol. Which numbered molecule would undergo dehydration most easily?

Answer: 4

Solution

Acid-catalysed dehydration proceeds through the most stable accessible carbocation; molecule (4), 2-phenylbutan-2-ol, ionises to a carbocation that is both tertiary and benzylic, gaining

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Question ID VK-149006