Which of the following give a silver mirror when warmed with Tollens reagent?

Amethanoic acid
B3-hydroxybutan-2-one
Cphenyl methyl ketone
Dbenzaldehyde

Answer: A, B, D

Methanoic acid (retains an aldehyde-like H-C=O unit), the alpha-hydroxy ketone 3-hydroxybutan-2-one and benzaldehyde all reduce Tollens reagent. Phenyl methyl ketone has no oxidisable group under these mild conditions.

Practice Aldehydes, Ketones and Carboxylic Acids More on Oxidation and reduction of carbonyls (Clemmensen, Wolff-Kishner, Tollens, Fehling)

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