Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 40AP
Interpretation Introduction
Interpretation:
To draw the three-dimensional furanose form of ascorbic acid.
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An oligosaccharide isolated from an organism is found tocontain two glucose residues and one galactose residue.Exhaustive methylation followed by hydrolysis producedtwo glucoses with methoxy groups at positions 2, 3,and 6 and galactose with methoxy groups at positions2, 3, 4, and 6. What is the structure of the originaloligosaccharide?
d-Altrose is an aldohexose. Ruff degradation of d-altrose gives the same aldopentose asdoes degradation of d-allose, the C3 epimer of glucose. Give the structure of d-altrose
Which D-aldopentoses are reduced to optically inactive alditols using NaBH4, CH3OH?
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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Show that Ruff degradation of d-mannose gives the same aldopentose (d-arabinose) asdoes d-glucose
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For D-lyxose i. Draw an epimer at C3. ii. Draw a diastereomer that is not an epimer. iii. Draw the anomers of -D-lyxofuranose and -D-lyxopyranose. iv. Draw the product as Haworth projection when reacted with methanol catalysed by acid.
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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?
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Predict the products obtained when d-galactose reacts with each reagent.(a) Br2 and H2O (b) NaOH, H2O (c) CH3OH, H + (d) Ag(NH3) 2+ -OH(e) H2, Ni (f) excess Ac2O and pyridine (g) excess CH3 I, Ag2O (h) NaBH4(i) Br2, H2O, then H2O2 and Fe2(SO4)3 (j) (1) KCN/HCN; (2) H2, Pd/BaSO4; (3) H3O! (k) excess HIO42
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d-Xylose and d-lyxose are formed when d-threose undergoes a Kiliani–Fischer synthesis. d-Xylose is oxidized to an optically inactive aldaric acid,whereas d-lyxose forms an optically active aldaric acid. What are the structures of d-xylose and d-lyxose?
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does structure E represent fructofuranose? explain
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Draw the α-d-tagatopyranose sugars using Haworth projections:
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Show the steps in converting Fischer to Haworth to:
Convert D-Talose to its aIpha pyranose structure.
Convert D-Tagatose to its beta furanose structure.
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Using Fischer projection structure where no cyclization took place, what product/s formed when D-galactose reacts with the following:
CN- , H+ ; H2O (hydrolysis); NaBH4
NaBH4
CH3OH, HCl
Acetic anhydride
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Draw Fischer projections for the product(s) formed by reaction of d-ribose with the following. In addition, state whether each product is optically active or inactive
Q. HNO3, warm
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The C2-epimer of D-xylose is called (blank 1). The enediol rearrangementconverts an aldose into a (blank 2). The aldopentose embedded in RNA is(blank 3). An aldopentose would have (blank 4) possible stereoisomers,of whichBlankwould be D-sugars. An ketopentose would have (blank 4) possiblestereoisomers, of which (blank 5) would be D-sugars
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Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a Daldotetrose that is oxidized to an optically active aldaric acid?
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