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

question 11

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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. 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: C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO<sub>3</sub> to give an optically active aldaric acid. - Wohl degradation followed by HNO<sub>3</sub> oxidation gives an optically inactive Aldaric acid. - Two Wohl degradations followed by HNO<sub>3</sub> oxidation give a meso-tartaric acid.   A)  A B)  B C)  C D)  D


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