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The compound that does not reduce Fehling solution is:

A

Glucose

B

Fructose

C

Sucrose

D

Maltose

Step-by-Step Solution

Reducing sugars are carbohydrates that can reduce reagents like Fehling's or Tollens' solution. To be a reducing sugar, the carbohydrate must have a free aldehyde or ketone group (or a hemiacetal/hemiketal group that can open to yield a free carbonyl in solution).

  • Glucose is an aldohexose and has a free aldehyde group, making it a reducing sugar.
  • Maltose is a disaccharide composed of two glucose units linked by an α(14)\alpha(1 \rightarrow 4) glycosidic bond. The second glucose unit retains a free hemiacetal group at its anomeric carbon (C-1), making it a reducing sugar.
  • Fructose is a ketohexose. Under the alkaline conditions of Fehling's test, it undergoes isomerization (Lobry de Bruyn-van Ekenstein transformation) to form glucose and mannose, which then reduce the reagent.
  • Sucrose is a disaccharide formed by an α,β(12)\alpha, \beta(1 \rightarrow 2) glycosidic linkage between the anomeric carbon of α\alpha-D-glucose (C-1) and the anomeric carbon of β\beta-D-fructose (C-2). Because both anomeric carbons are involved in the bond, there is no free reducing group available. Hence, sucrose is a non-reducing sugar and does not reduce Fehling's solution.
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