Monosaccharide A is a D-aldotetrose. Treatment of A with nitric acid gives an optically inactive aldaric acid (B). Killiani-Fischer chain extension of A gives two products (C & D). C on treatment with NABH4, gives an alditol (E) that is optically active. D gives an alditol (F) that is NOT optically active. Give Fischer projections for A, B, CD, E, and E.

The Products of the reaction of L-glucose with the following L-glucose [1] NH2NH4 [2] Ac20,NaOAc [3] NaOCH3

NAIME H 1) Compound X consists of an aldopentose. If X is oxidized with nitric acid, the product is then optically active. If X undergoes one Ruff degradation and the product of that degradation is reduced to the alditol using H₂/Ni the resulting product is optically inactive. If compound X undergoes two Ruff degradations, D-glyceraldehyde (below) is obtained. Draw the usual Fischer projection of X (aldehyde at the top). (Hint: work backward from D- glyceraldehyde.) C10 Organic Chemistry 2: Homework assignment H-C-OH Carbohydrates CH₂OH D-Glyceraldehyde