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Question #44995
The Question
An aqueous solution of a naturally occurring, non-reducing disaccharide () is hydrolyzed with dilute to yield a single D-aldohexose . forms an osazone identical to that formed by D-fructose. is subjected to the following reaction sequence: where and are isomeric aldoheptoses. Subsequent oxidation of and with warm concentrated yields heptaric acids and , respectively. Which of the following correctly describes the stereochemical relationship between and , and the optical activity of and ?
Options
- A.
C2-epimers; exactly one meso compound
- B.
C2-epimers; both optically active
- C.
C3-epimers; exactly one meso compound
- D.
Enantiomers; both optically inactive
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
Disaccharide Hydrolysis Products|Kiliani-Fischer Chain Extension|D-Glucose Anomeric Equilibrium
Why This Question Is Tricky
Common Mistakes
The question tests the student's ability to integrate carbohydrate identification with stereochemical transformations.
The 'Hidden Variable' is the symmetry of the resulting heptaric acids.
Students often assume that chain extension of a chiral molecule like D-glucose will exclusively yield chiral derivatives (Option B).
The trap is failing to draw the full 7-carbon Fischer projection to recognize that one of the C2-epimers perfectly aligns its new stereocenter with the existing asymmetric carbons to create a meso compound (plane of symmetry at C4).
Furthermore, if a student incorrectly identifies as D-mannose, stereochemical analysis would incorrectly lead them to Option B, rewarding only those who correctly identify Trehalose.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Disaccharide Hydrolysis Products |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |