JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

major product 'A' formed in the above reaction is

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

Answer: (D)

Solution

The substrate is indane-1,2,3-trione, in which the central carbonyl is flanked on both sides by carbonyl groups and is therefore strongly electrophilic. A molecule of water adds across this central carbonyl to form a stable gem-diol (hydrate), the stability arising from relief of strain between the adjacent carbonyls and from intramolecular hydrogen bonding to the flanking

C = O

groups. Product A is 2,2-dihydroxyindane-1,3-dione, the hydrate commonly known as ninhydrin.

JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Single correct option

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