After a series of KilianiFischer syntheses on an unknown sugar is isolated from the

Chapter 0, Problem 23-63

(choose chapter or problem)

After a series of KilianiFischer syntheses on an unknown sugar is isolated from the reaction mixture. The following experimental information is obtained: (1) Molecular formula (2) Undergoes mutarotation. (3) Reacts with bromine water to give an aldonic acid. (4) Reacts with phenylhydrazine to give an osazone, mp 178 C. (5) Reacts with to give an optically active aldaric acid. (6) Ruff degradation followed by oxidation gives an optically inactive aldaric acid. (7) Two Ruff degradations followed by oxidation give meso-tartaric acid. (8) Formation of the methyl glycoside (using and HCl), followed by periodic acid oxidation, gives a mixture CH3OH HNO3 HNO3 HNO3 C6H12O6. 1+2-glyceraldehyde, of products that includes (a) Draw a Fischer projection for the open-chain form of this unknown sugar. Use Figure 23-3 to name the sugar. (b) Draw the most stable conformation of the most stable cyclic hemiacetal form of this sugar, and give the structure a complete systematic name