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Question #44963

Difficulty: 8/10 | 🟢 Free

The Question

An optically active \ce{D}-ketohexose X\textbf{X} gives a positive Tollens' test. In the alkaline medium of the reagent, X\textbf{X} undergoes the Lobry de Bruyn–van Ekenstein transformation via an intermediate I\textbf{I} to form an equilibrium mixture containing X\textbf{X} and two aldohexoses Y\textbf{Y} and Z\textbf{Z}. Oxidation of Y\textbf{Y} and Z\textbf{Z} with warm \ce{HNO3} yields aldaric acids P\textbf{P} and Q\textbf{Q}, respectively. It is observed that P\textbf{P} is optically inactive (meso) while Q\textbf{Q} is optically active. Which of the following correctly identifies X\textbf{X}, the intermediate I\textbf{I}, and the stereochemical relationship between Y\textbf{Y} and Z\textbf{Z}?

Options

  • A.

    X\textbf{X} = \ce{D}-Tagatose; I\textbf{I} = 1,2-enediol; Y\textbf{Y} and Z\textbf{Z} are C-2 epimers

  • B.

    X\textbf{X} = \ce{D}-Fructose; I\textbf{I} = 1,2-enediol; Y\textbf{Y} and Z\textbf{Z} are C-2 epimers

  • C.

    X\textbf{X} = \ce{D}-Sorbose; I\textbf{I} = 1,2-enediol; Y\textbf{Y} and Z\textbf{Z} are C-2 epimers

  • D.

    X\textbf{X} = \ce{D}-Tagatose; I\textbf{I} = 2,3-enediol; Y\textbf{Y} and Z\textbf{Z} are C-3 epimers

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Reducing Sugar Criteria|D-Glucose Anomeric Equilibrium|Epimerization vs Anomerization

Why This Question Is Tricky

Common Mistakes

This question tests the hidden mechanism of the Lobry de Bruyn–van Ekenstein transformation and stereochemical analysis of aldaric acids.

Students often blindly associate a positive Tollens' test for ketoses exclusively with D-Fructose.

The trap is failing to evaluate the stereochemistry of the resulting aldaric acids.

D-Fructose yields two optically active aldaric acids, whereas D-Tagatose yields one meso (galactaric acid) and one optically active (talaric acid) product, correctly satisfying the conditions.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterBiomolecules - Class 12
ConceptReducing Sugar Criteria
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree