JEE Main · 2023 · 13 Apr 2023 · Shift 1 · Alcohols Phenols and Ethers

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For the given reaction

(see structure)

The total number of possible products formed by tertiary carbocation of A is ______.

Answer: 4

Solution

Protonation and loss of water from the alcohol first give a secondary carbocation. A 1,2-hydride shift turns it into one tertiary carbocation, while a 1,2-methyl shift turns it into a second tertiary carbocation. Each of these tertiary carbocations can lose a

β

-proton in two distinct directions, so each yields two alkenes. Counting the constitutionally different alkenes obtained from the two tertiary carbocations, the total number of products formed is four.

JEE Main · 2023 · 13 Apr 2023 · Shift 1 · Integer answer

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