You have a D-aldotriose.
You perform Kiliani-Fischer synthesis on this sugar (1. CN-/HCN, 2. H2 on poisoned catalyst 3. H3O+), and receive two products. You take one of those two products (let’s call it product A) and then subject it nitric acidoxidation. The resultant sugar is optically inactive.
You perform a subsequent Kiliani-Fischer synthesis on product A from the previous paragraph, and receive two sugars. You choose one at random (let’s call this one product B), treat it with nitric acid, and the resultant sugar is optically active.
You perform a subsequent Kiliani-Fischer synthesis on product B from the previous paragraph, and receive two sugars. You choose the sugar with an “R” stereocenter at the “2nd” carbon (the first chiral center). Let’s call this product C.
What is product C – the final sugar in this sequence.
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
