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 oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?
A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, 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?
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?
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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- Monosaccharide A is a diastereomer of d-lyxose. Treatment of A with nitric acid forms an optically inactive aldaric acid. A undergoes a Kiliani-Fischer synthesis to form B and C. B is oxidized by nitric acid to an optically active aldaric acid, and C is oxidized to an optically inactive aldaric acid. Wohl degradation of A forms D, which is oxidized by nitric acid to an optically inactive aldaric acid. Wohl degradation of D forms a d-aldotriose. Identify A, B, C, and D.arrow_forwardIdentify compounds A–D. A D-aldopentose A is oxidized with HNO3 to an optically inactive aldaric acid B. A undergoes the Kiliani–Fischer synthesis to yield C and D. C is oxidized to an optically active aldaric acid. D is oxidized to an optically inactive aldaric acidarrow_forwardCompound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.arrow_forward
- Draw the following monosaccharides, using chair conformations for the pyranoses andHaworth projections for the furanoses.(a) a-d-mannopyranose (C2 epimer of glucose)(b) b-d-galactopyranose (C4 epimer of glucose)(c) b-d-allopyranose (C3 epimer of glucose)(d) a-d-arabinofuranose(e) b-d-ribofuranose (C2 epimer of arabinose)arrow_forwardA 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?arrow_forwardDraw the following sugar derivatives.(a) methyl b-d-glucopyranosidearrow_forward
- There 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_forwardAldohexoses 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.arrow_forwardIdentify the carbon containing the hemiacetal functional group in the ring form of fructose (1,3,4,5,6-pentahydroxyhexan-2-one). A B C Darrow_forward
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