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Question #44962

Difficulty: 8/10 | 🟢 Free

The Question

A synthetic non-reducing disaccharide X\mathbf{X} is synthesized by linking the anomeric carbon of D-galactofuranose to the anomeric carbon of D-glucopyranose via an α(1↔1)α\alpha(1\leftrightarrow 1)\alpha glycosidic bond.

\textbf{Experiment 1:} 1 mol1\text{ mol} of X\mathbf{X} is treated with an excess of periodic acid (\ce{HIO4}) in aqueous solution at 298 K298\text{ K}. \textbf{Experiment 2:} 1 mol1\text{ mol} of X\mathbf{X} is subjected to mild acid hydrolysis (0.01 M HCl0.01\text{ M HCl}, 298 K298\text{ K}) until equilibrium is reached. The resulting solution is neutralized and then heated with an excess of Fehling's solution.

Let PP be the moles of \ce{HIO4} consumed in Experiment 1. Let QQ be the moles of formic acid (\ce{HCOOH}) produced in Experiment 1. Let RR be the moles of formaldehyde (\ce{HCHO}) produced in Experiment 1. Let SS be the moles of \ce{Cu2O} precipitated in Experiment 2.

Determine the values of P,Q,R,P, Q, R, and SS.

Options

  • A.

    P=4P=4, Q=1Q=1, R=1R=1, S=2S=2

  • B.

    P=4P=4, Q=2Q=2, R=0R=0, S=0S=0

  • C.

    P=4P=4, Q=1Q=1, R=1R=1, S=0S=0

  • D.

    P=3P=3, Q=0Q=0, R=1R=1, S=2S=2

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Exception_Exposure

Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.

Concepts Behind This Question

Reducing Sugar Criteria|Glycosidic Linkage Geometry|Disaccharide Hydrolysis Products

Why This Question Is Tricky

Common Mistakes

The problem tests two major hidden variables.

First, the differential kinetic stability of glycosidic linkages: while standard 1,1-pyranosyl-pyranoside linkages (like in trehalose) are highly resistant to mild acid hydrolysis, furanosides are kinetically labile due to ring strain and rapidly hydrolyze, exposing the hemiacetals.

Students relying on the rote rule '1,1-linkages are non-reducing and stable' will incorrectly predict S=0.

Second, it tests the precise structural mapping of furanose vs pyranose rings during HIO4 oxidation, specifically identifying that an aldohexofuranose has an exocyclic vicinal diol (C5-C6) that yields formaldehyde, unlike its pyranose counterpart.

Quick Facts About This Question

Question Information

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