Question 9

MCQMEDIUM

The correct statement(s) regarding sugars is(are)

Given: Specific rotations of L−(–)L-(\text{--})-glucose and L-(+)L\text{-(+)}-fructose are −52.5∘-52.5^{\circ} and +92.5∘+92.5^{\circ}, respectively.

(A) On treatment with HNO3HNO_3, gluconic acid is oxidized to saccharic acid, whereas glucose is not oxidized to saccharic acid. (B) Fructose gives a positive Fehling's test because it isomerises to glucose and another aldohexose in the presence of Fehling's reagent. (C) Invert sugar is an equimolar mixture of DD-glucose and DD-fructose formed after hydrolysis of the corresponding disaccharide. (D) Specific rotation of invert sugar is −40∘-40^{\circ}.

(A)

On treatment with HNO3HNO_3, gluconic acid is oxidized to saccharic acid, whereas glucose is not oxidized to saccharic acid.

(B)

Fructose gives a positive Fehling's test because it isomerises to glucose and another aldohexose in the presence of Fehling's reagent.

(C)

Invert sugar is an equimolar mixture of DD-glucose and DD-fructose formed after hydrolysis of the corresponding disaccharide.

(D)

Specific rotation of invert sugar is −40∘-40^{\circ}.

Detailed Solution

Analyze each option: (A) Both glucose and gluconic acid are oxidized by concentrated HNO3HNO_3 to saccharic acid (a dicarboxylic acid). The reagent oxidizes both the aldehyde/hemicetal group and the primary alcohol group. So, the statement is false. (B) Fructose is a ketohexose and usually does not reduce Fehling's solution. however, in the presence of basic reagents like Fehling's solution, it undergoes Lobry de Bruyn-van Ekenstein rearrangement to form glucose and mannose (another aldohexose), which then give a positive test. This is correct. (C) Invert sugar is indeed the equimolar mixture of DD-glucose and DD-fructose obtained by the hydrolysis of sucrose (a disaccharide). This is correct. (D) Using the standard values for DD-isomers: Specific rotation of DD-glucose is +52.5∘+52.5^{\circ} and DD-fructose is −92.5∘-92.5^{\circ}. For an equimolar mixture, the specific rotation is the average: +52.5∘+(−92.5∘)2=−20∘\frac{+52.5^{\circ} + (-92.5^{\circ})}{2} = -20^{\circ}. The value −40∘-40^{\circ} is incorrect.

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