Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.28P
Interpretation Introduction
Interpretation:
The structure of aldehexose A which on reaction with nitric acid gives aldaric acid is to be identified
Concept introduction:
Aldoses are the carbohydrates in which an
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How many asymmetric carbons and stereoisomers are there for an aldohexose? For aketohexose?
An important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.
How many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Prob. 24.3PCh. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Prob. 24.16PCh. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Prob. 24.19PCh. 24 - Prob. 24.20PCh. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Prob. 24.24PCh. 24 - Prob. 24.25PCh. 24 - Prob. 24.26PCh. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - Prob. 24.34APCh. 24 - Prob. 24.35APCh. 24 - Prob. 24.36APCh. 24 - Prob. 24.37APCh. 24 - Prob. 24.38APCh. 24 - Prob. 24.39APCh. 24 - Prob. 24.40APCh. 24 - Prob. 24.41APCh. 24 - Prob. 24.42APCh. 24 - Prob. 24.43APCh. 24 - Prob. 24.44APCh. 24 - Prob. 24.45APCh. 24 - Prob. 24.46APCh. 24 - Prob. 24.47APCh. 24 - Prob. 24.49APCh. 24 - Prob. 24.50APCh. 24 - Prob. 24.51APCh. 24 - Prob. 24.52APCh. 24 - Prob. 24.53APCh. 24 - Prob. 24.54APCh. 24 - Prob. 24.55APCh. 24 - Prob. 24.56APCh. 24 - Prob. 24.57APCh. 24 - Prob. 24.58APCh. 24 - Prob. 24.59APCh. 24 - Prob. 24.60APCh. 24 - Prob. 24.61APCh. 24 - Prob. 24.62AP
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- A) Draw the structure of any aldohexose in the pyranose ring form. B) Draw the structure of the anomer of the aldohexose you drew above. C) How many asymmetric carbons (chiral centers) does each of these structures have? D) How many stereoisomers of the aldohexoses you drew are theoretically possible?arrow_forwardCarbohydrates in nature are only found in D-form L-form or both ?arrow_forwardA 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?arrow_forward
- is this monosaccharide aldose or ketose? what is the chemical group and its location that allows its classification.arrow_forwardA reddish color is obtained when compound A (a disaccharide) is reacted with Benedict solution. Is this compound more likely maltose or sucrosearrow_forwardDraw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimersarrow_forward
- D-Glucose most often exists as a pyranose, but it can also exist as a furanose. Draw the Haworth projection of α-d-glucofuranose.arrow_forward1. Identify the anomeric carbons on sucrose and explain how they are different from lactose and cellulose. 2. On Wikipedia (image pictures below) sucrose is labeled β-D-Fructofuranosyl α-D-glucopyranoside. But the anomeric carbon has the oxygen pointing down and other stereocenters inverted from that of fructose. Did Wikipedia incorrectly name it? Or can you explain why this is the case using structures of sucrose, fructose and glucose…arrow_forwardHow many stereoisomers are possible for an aldopentose?arrow_forward
- Give the full proper name. Is this a reducing sugar and if it is what is the reducing sugar? Is the monosaccharide an aldose or Ketose?arrow_forwardTrehalose and isomaltose are both dimers of glucose. However, they have considerablydifferent reactivities. Concisely explain why these differences are observed.arrow_forwardThe anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forward
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