Tollen's reagent reacts with free aldehydes.
Structure A is a hemiacetal (reducing sugar) that exists in equilibrium with its open-chain aldehyde form, allowing it to react with Tollen's reagent.
Structure B is a glycoside (methyl glycoside or similar), where the anomeric carbon is locked in an acetal/ketal form with an -OCH₃ group, preventing ring opening and aldehyde formation, so it cannot react with Tollen's.
Structure C has a cyclic ether oxygen and lacks a free aldehyde group that can be generated under mild conditions, preventing reaction with Tollen's.
Structure D is a hemiacetal form of a reducing sugar with a free anomeric -OH, allowing equilibrium with the aldehyde form and reaction with Tollen's.
Structures B and C do not react with Tollen's reagent.
