You have an unknown sugar. It is a D-aldohexose with an “S” stereocenter at the “first” chiral carbon. You treat the sugar with nitric acid. The resulting compound is optically active.
You perform Wohl-Degradation on this sugar (1. NH2OH, 2. Acetic Anhydride, 3. OH-), and then subject the resultant sugar to nitric acid oxidation. The resultant sugar is optically inactive.
You perform a subsequent Wohl-Degradation (so two total degradations at this point), followed by oxidation, and receive an optically active compound.
What is your sugar?
Select one:
a. D-Allose
b. D-Altrose
c. D-glucose
d. D-mannose
e. D-gulose
f. D-idose
g. D-galactose
h. D-talose
