JEE Main · 2022 · 26 Jun 2022 · Shift 1 · Alcohols Phenols and Ethers

Consider the above reaction sequence and identify the product

B

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

The starting material is acetylacetone (2,4-pentanedione). When treated with Grignard reagent (methylmagnesium bromide), nucleophilic addition occurs at both carbonyl groups. After hydrolysis, a tertiary diol is formed. The product B is 2,4-dimethyl-2,4-pentanediol, shown in option (A). Although acetylacetone can undergo acid-base reaction due to its active methylene group, under these conditions with excess Grignard reagent, nucleophilic addition dominates.

JEE Main · 2022 · 26 Jun 2022 · Shift 1 · Single correct option

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