Fundamentals of Organic ChemistryChemistryBiomolecules
Fructose reduces Fehling's solution due to the presence of:
Options
- Aa hydroxy group
- Ban aldehyde group
- Can -hydroxyketone group
- Da ketone group
Correct answer
C. an -hydroxyketone group
Step-by-step solution
Fructose is a ketose sugar containing an -hydroxyketone group. Under the alkaline conditions of Fehling's solution, the -hydroxyketone group undergoes tautomerization (Lobry de Bruyn-van Ekenstein transformation) to form an enediol intermediate. This intermediate further converts into an aldose (glucose and mannose) which contains an aldehyde group. The newly formed aldehyde group then reduces Fehling's solution. Thus, the reducing property of fructose is due to the presence of the -hydroxyketone group. Answer: an