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Question #44992
The Question
An optically active aldopentose undergoes the Kiliani-Fischer chain extension sequence: (i) , (ii) , , (iii) , pH 3-5. This yields a mixture of two aldohexoses, and . When and are separately heated with excess phenylhydrazine () in an acetate buffer at , they consume and moles of phenylhydrazine per mole of sugar, respectively, to form osazone derivatives and . Which of the following correctly describes the relationship between and , the values of and , and the number of chiral carbons in ?
Options
- A.
Identical; ; 3 chiral carbons
- B.
Diastereomers; ; 4 chiral carbons
- C.
Identical; ; 3 chiral carbons
- D.
Enantiomers; ; 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
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Kiliani-Fischer Chain Extension |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |