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.

Question

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The Answer of 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