After a Series of Kiliani-Fischer Syntheses on D-Glyceraldehyde,an Unknown Sugar

question 12

Multiple Choice

After a series of Kiliani-Fischer syntheses on D-glyceraldehyde,an unknown sugar was isolated from the reaction mixture.The following experimental data was obtained.What is the structure of this unknown sugar? Data:
- Molecular formula: C₆H₁₂O₆
- Reacts with phenylhydrazine to give an osazone,mp 178°C.
- Reacts with HNO₃ to give an optically active aldaric acid.
- Wohl degradation followed by HNO₃ oxidation gives an optically inactive
Aldaric acid.
- Two Wohl degradations followed by HNO₃ oxidation give a meso-tartaric acid.

• A)A
• B)B
• C)C

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