JEE Main · 2021 · 17 Mar 2021 · Shift 1 · Chapter_pending

The product " A " in the above reaction is:

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

Answer: (C)

Solution

Ethylene glycol with an acid catalyst converts a carbonyl group into a cyclic 1,3-dioxolane. In ethyl acetoacetate the ketone carbon is far more electrophilic than the ester carbon, whose carbonyl is already stabilised by donation from the alkoxy oxygen, so only the keto group is attacked and the ester survives untouched. The product is ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate, that is, the ketone protected as its five-membered cyclic ketal with the ethoxycarbonyl group intact.

JEE Main · 2021 · 17 Mar 2021 · Shift 1 · Single correct option

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