JEE Main Chemistry question

Fructose reduces Tollens' reagent due to:

(A)Asymmetric carbons
(B)Primary alcoholic group
(C)Secondary alcoholic group
(D)Enolisation of fructose followed by conversion to aldehyde by baseCorrect

Answer: (D)

Solution

Although fructose is a ketose, under the mildly basic conditions of Tollens' reagent it undergoes base-catalysed enolisation (via the Lobry de Bruyn–Alberda van Ekenstein rearrangement), which interconverts it with glucose and mannose through a common enediol intermediate;

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Question ID VK-151086