JEE Challenger
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Identification of Reducing Properties and Glucosidic Linkages in Sugars X and Y

The correct statement(s) about the following sugars X\mathbf{X} and Y\mathbf{Y} is(are)

Diagram 0

Options

A

X\mathbf{X} is a reducing sugar and Y\mathbf{Y} is a non-reducing sugar

B

X\mathbf{X} is a non-reducing sugar and Y\mathbf{Y} is a reducing sugar

Correct
C

The glucosidic linkages in X\mathbf{X} and Y\mathbf{Y} are α\alpha and β\beta, respectively

Correct
D

The glucosidic linkages in X\mathbf{X} and Y\mathbf{Y} are β\beta and α\alpha, respectively

Topics & Concepts

Step-by-Step Solution

To determine the correct statements about sugars X\mathbf{X} and Y\mathbf{Y}, we analyze their structures, the nature of their anomeric carbons, and the stereochemistry of their glycosidic linkages.


1. Analysis of Sugar X\mathbf{X} (Sucrose):

  • Structure: Sugar X\mathbf{X} is composed of an α-D\alpha\text{-D}-glucopyranosyl unit linked to a β-D\beta\text{-D}-fructofuranosyl unit.
  • Linkage Stereochemistry:
    • At the C-1\text{C-1} anomeric center of the glucose ring, the glycosidic bond is oriented downwards (axial/α\alpha-configuration relative to the ring with the −CH2OH-\text{CH}_2\text{OH} group at C-5\text{C-5} oriented upwards).
    • Therefore, the glucosidic linkage in X\mathbf{X} is an α\alpha-linkage (α-D-(1→2)−β-D\alpha\text{-D-(1}\to\text{2)}-\beta\text{-D} linkage).
  • Reducing Nature:
    • The glycosidic bond is formed between the anomeric carbon (C-1\text{C-1}) of glucose and the anomeric carbon (C-2\text{C-2}) of fructose.
    • Since both anomeric carbons are tied up in the glycosidic bond, there are no free hemiacetal or hemiketal groups capable of opening into a free aldehyde or ketone.
    • Thus, X\mathbf{X} is a non-reducing sugar.

2. Analysis of Sugar Y\mathbf{Y} (Cellobiose-type Disaccharide):

  • Structure: Sugar Y\mathbf{Y} consists of two pyranose rings linked via a glycosidic bond between C-1\text{C-1} of the left ring and C-4\text{C-4} of the right ring.
  • Linkage Stereochemistry:
    • At the C-1\text{C-1} anomeric carbon of the left glucose ring, the glycosidic oxygen is oriented upwards (equatorial/β\beta-configuration, cis to the −CH2OH-\text{CH}_2\text{OH} group at C-5\text{C-5}).
    • Therefore, the glucosidic linkage in Y\mathbf{Y} is a β\beta-linkage (β-(1→4)\beta\text{-(1}\to\text{4)} linkage).
  • Reducing Nature:
    • The right-hand pyranose ring has a free hemiacetal group at its anomeric carbon (C-1\text{C-1} has an −OH-\text{OH} group).
    • This hemiacetal group can undergo mutarotation and open to form a free aldehyde in aqueous solution, which can reduce Fehling's solution or Tollens' reagent.
    • Thus, Y\mathbf{Y} is a reducing sugar.

Conclusion:

  • Statement (B): X\mathbf{X} is a non-reducing sugar and Y\mathbf{Y} is a reducing sugar. (Correct)
  • Statement (C): The glucosidic linkages in X\mathbf{X} and Y\mathbf{Y} are α\alpha and β\beta, respectively. (Correct)

Therefore, the correct options are B and C.