Before You Begin
Question #44977
The Question
An aldopentose upon oxidation with dilute yields an optically active aldaric acid. is subjected to Kiliani-Fischer synthesis (using , followed by hydrolysis and reduction) to yield two aldohexoses, and . Oxidation of with yields an optically inactive (meso) aldaric acid, whereas yields an optically active aldaric acid. and are then individually reacted with 3 equivalents of phenylhydrazine () at to form osazones and respectively. What is the relationship between and , and how many chiral centers are present in the osazone product?
Options
- A.
Identical, 3 chiral centers
- B.
Diastereomers, 4 chiral centers
- C.
Identical, 4 chiral centers
- D.
Enantiomers, 3 chiral centers
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
Osazone Formation Logic|Kiliani-Fischer Chain Extension
Why This Question Is Tricky
Common Mistakes
The question tests the deduction of sugar stereochemistry via symmetry in aldaric acids and the mechanistic outcome of the Kiliani-Fischer synthesis.
The core trap exploits osazone formation: students often forget that C-2 epimers (created during chain extension) converge to an identical osazone because the C-2 stereocenter is converted to an hybridized carbon.
Additionally, miscounting the chiral centers in the osazone (assuming 4 instead of 3) is a frequent stereochemical trap.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Osazone Formation Logic |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |