Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 68AP
Interpretation Introduction
Interpretation:
The respective structure can be deduced from the following clue.
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A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two Daldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?
A D-aldohexose A is formed from an aldopentose B by the Kiliani–Fischer synthesis. Reduction of A with NaBH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?
Aldohexoses A and B are formed from aldopentose C via a Kiliani–Fischer synthesis. Nitric acid oxidizes A to an optically active aldaric acid, B to an optically inactive aldaric acid, and C to an optically active aldaric acid. Wohl degradation of C forms D, which is oxidized by nitric acid to an optically active aldaric acid. Wohl degradation of D forms (+)-glyceraldehyde. Identify A, B, C, and D.
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- An unknown reducing disaccharide is found to be unaffected by invertase enzymes. Treatment with an a@galactosidasecleaves the disaccharide to give one molecule of d-fructose and one molecule of d-galactose. When the disaccharideis treated with excess iodomethane and silver oxide and then hydrolyzed in dilute acid, the products are2,3,4,6-tetra-O-methylgalactose and 1,3,4-tri-O-methylfructose. Propose a structure for this disaccharide, and give itscomplete systematic name.arrow_forwardThere are three (3) vials labeled A, B, and C known to contain the following monosaccharides. All three samples reduce Tollens and Fehling. By oxidation with dilute HNO3 an optically active aldaric acid is obtained for sample A and the remaining two give products without optical activity. When the three samples were subjected to an alkaline medium, it was observed that, after a certain time, samples A and C reached the same value of the specific rotation [α]. Select the RIGHT alternative: (a) Sample A is Galactose. (b) Sample B is Alosa. (c) Samples A and C are not related to each other by an epimerization process. (d) Sample C is Talose. (e) Samples B and C are epimers.arrow_forwardD-glucose and L-glucose would be expected to show differences in which of the followingp roperties? (Answer the items as dif erent or not different) a. Solubility in an achiral solvent b. Density c. Melting point d. Solubility in a chiral solvent e. Freezing point f. Reaction with ethanol (achiral compound) g. Reaction with (+)-lactic acid (chiral compound)arrow_forward
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