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Question #44578

Difficulty: 8/10 | 🟢 Free

The Question

Pure β\beta-D-glucopyranose ([α]D=+18.7∘[\alpha]_D = +18.7^\circ) is dissolved in an aqueous buffer at 298 K containing a large excess of a transition metal ion, M2+M^{2+}. The ion M2+M^{2+} forms a kinetically inert and thermodynamically highly stable chelate complex (CC, [α]D=+120∘[\alpha]_D = +120^\circ) exclusively with the \textit{cis}-1,2-diol system present in α\alpha-D-glucopyranose ([α]D=+112∘[\alpha]_D = +112^\circ). The β\beta-anomer does not coordinate with M2+M^{2+}. Assuming the chelate CC remains completely intact, what is the final specific rotation of the carbohydrate species in solution at equilibrium, and what is the observation when this final solution is treated with Br2/H2OBr_2/H_2O?

Options

  • A.

    +120∘+120^\circ; Bromine water is not decolorized.

  • B.

    +52.7∘+52.7^\circ; Bromine water is decolorized.

  • C.

    +18.7∘+18.7^\circ; Bromine water is not decolorized.

  • D.

    +120∘+120^\circ; Bromine water is decolorized.

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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

Optical Isomerism Logic|D-Glucose Anomeric Equilibrium|Reducing Sugar Criteria

Why This Question Is Tricky

Common Mistakes

This problem tests the intersection of dynamic equilibrium (mutarotation) and coordination chemistry.

Students often rote-memorize that 'glucose is a reducing sugar' and 'glucose mutarotates to +52.7∘+52.7^\circ'.

The trap is failing to recognize that mutarotation and reducing properties strictly depend on the availability of the free hemiacetal hydroxyl to undergo reversible ring-opening.

By introducing a metal ion that selectively chelates the cis-1,2-diol of the α\alpha-anomer, the equilibrium is thermodynamically driven to 100% complexation via Le Chatelier's Principle.

Furthermore, the coordinate bond locks the anomeric center, stripping the molecule of its reducing properties.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterCoordination Compounds - Class 12
ConceptOptical Isomerism Logic
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree