The compound shown gives no silver mirror. Select all of the structures shown that give a silver mirror with Tollens' reagent. (Tollens' reagent oxidises aldehydes and also alpha-hydroxy ketones, which tautomerise to enediols.)

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B, D

Tollens' reagent oxidises aldehydes and also alpha-hydroxy ketones (they tautomerise to enediols). B (hydroxyacetone) and D (benzaldehyde) give the mirror. Acetophenone (A) and pentan-3-one (C) are simple ketones.

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