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Question #44992

Difficulty: 8/10 | 🟢 Free

The Question

An optically active aldopentose P\textbf{P} undergoes the Kiliani-Fischer chain extension sequence: (i) \ceHCN/KCN\ce{HCN / KCN}, (ii) \ceH3O+\ce{H3O+}, Δ\Delta, (iii) \ceNa(Hg),H2O\ce{Na(Hg), H2O}, pH 3-5. This yields a mixture of two aldohexoses, Q\textbf{Q} and R\textbf{R}. When Q\textbf{Q} and R\textbf{R} are separately heated with excess phenylhydrazine (\cePhNHNH2\ce{PhNHNH2}) in an acetate buffer at 100∘C100^\circ\text{C}, they consume xx and yy moles of phenylhydrazine per mole of sugar, respectively, to form osazone derivatives OQ\textbf{O}_Q and OR\textbf{O}_R. Which of the following correctly describes the relationship between OQ\textbf{O}_Q and OR\textbf{O}_R, the values of xx and yy, and the number of chiral carbons in OQ\textbf{O}_Q?

Options

  • A.

    Identical; x=y=3x = y = 3; 3 chiral carbons

  • B.

    Diastereomers; x=y=3x = y = 3; 4 chiral carbons

  • C.

    Identical; x=y=2x = y = 2; 3 chiral carbons

  • D.

    Enantiomers; x=y=2x = y = 2; 4 chiral carbons

Check Your Answer

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

Kiliani-Fischer Chain Extension|Epimerization vs Anomerization|Osazone Formation Logic

Why This Question Is Tricky

Common Mistakes

The question tests the stereochemical consequences of the Kiliani-Fischer synthesis and osazone formation.

The 'Trap' is the assumption that the diastereomeric mixture of epimers generated in the chain extension will lead to different osazones.

Students often forget that osazone formation oxidizes C-2, erasing the newly formed stereocenter and causing the two epimers to converge into an identical product.

Additionally, students frequently miscount the moles of phenylhydrazine consumed (guessing 2 instead of 3) or miscalculate the remaining chiral centers.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterBiomolecules - Class 12
ConceptKiliani-Fischer Chain Extension
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree