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Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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D-Aldopentose A is oxidized to an optically inactive aldaric acid. On Wohl degradation, A forms an aldotetrose B that is oxidized to an optically active aldaric acid. What are the structures of A and B?
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- Which of the compounds are achiral? Identify the relationship of A with BCD.arrow_forwardWhat D-aldohexose forms the same osazone as D-glucose?arrow_forwardCarbohydrates a. Compound Z is an aldopentose. If Z is oxidized with nitric acid the product is optically active. If Z 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 Z undergoes two Ruff degradations, D-glyceraldehyde (shown below) is obtained. Draw the usual Fischer projection of Z (aldehyde at the top). (Hint: work backwards from D- glyceraldehyde.) H HIC OH CH₂OH D-Glyceraldehydearrow_forward
- 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.arrow_forwardAldotetroses exist in the furanose form. Draw both anomers of D-erythrose.arrow_forwardDraw an electron pushing mechanism for proline racemization. Draw a reaction coordinate diagram of the uncatalyzed and catalyzed reaction.arrow_forward
- A 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and Dtalitol. What is the structure of the 2-ketohexose?arrow_forwardPlease draw the expanded structure of D-tagatose and its Fischer Projection (chiral C represented as a cross).arrow_forwardWhen d-tagatose is added to a basic aqueous solution, an equilibrium mixture of monosaccharides is obtained, two of which are aldohexoses and two of which are ketohexoses. Identify the aldohexoses and ketohexoses.arrow_forward
- When a sugar, xylose, is reduced an aldose a ketose O xylotic acid xylose cannot be oxidized xylitolarrow_forwardA 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and D-talitol. What is the structure of the 2-ketohexose?arrow_forwardWhen d-glucose is reduced with sodium borohydride, optically active glucitol results.When optically active d-galactose is reduced, however, the product is optically inactive.Explain this loss of optical activityarrow_forward
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