Fructose reduces Tollens' reagent due to
- asymmetric carbons
- primary alcoholic group
- secondary alcoholic group
- enolisation of fructose followed by conversion to aldehyde by base
Answer
(4) enolisation of fructose followed by conversion to aldehyde by base
Solution
Fructose is a ketohexose (keto group at C-2), yet it reduces Tollens' reagent.
∵ In the alkaline medium of the reagent, fructose undergoes enolisation (enediol formation) and rearranges to an aldose (glucose/mannose), i.e. an aldehyde (Lobry de Bruyn–van Ekenstein rearrangement).
⇒ The aldehyde formed reduces [Ag(NH3)2]+ to silver.
Answer: (4)