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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.6, Problem 22P
Interpretation Introduction
Interpretation:
To determine the reactant from the products mentioned.
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How many asymmetric carbons and stereoisomers are there for an aldohexose? For aketohexose?
In addition to lactose, D-galactose and D-glucose can form different heterodisaccharides. Draw the structures (Haworth projections) of the (i) a-glucose-(1→1) -a-galactose and ii) a- glucose-(1→3)-?-galactose, two examples of heterodisaccharides that can form.
Provide an explanation for the fact that α-D-mannose is more stable thanβ-D-mannose, whereas the opposite is true for glucose.
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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- (a) Draw the condensed structural formula, and give the name for the dipeptide Pro-Asn. (b) Draw the disaccharide formed by the following two monosaccharide via 1,4-linkage. In your disaccharide structure, circle and label the anomeric carbon and indicate whether you have an alpha (a) or a beta (B) anomer. CH2OH CH₂OH ОН ОН ОН ОН, ОН ОН ОН ОНarrow_forwardHow many constitutional isomers of acyclic monosaccharides are there that can be classified as aldohexoses? As ketohexoses?arrow_forwardWhich of the following monosaccharides gives optically inactive alditols on reduction with D-Glucose; L-Galactose D-Allose; D-Galactose L-Talose; D-Allose D-Altrose; D-Galactose NaBH,arrow_forward
- Monosaccharides can be categorized in terms of thenumber of carbon atoms (pentoses have five carbons andhexoses have six carbons) and according to whether theycontain an aldehyde (aldo- prefix, as in aldopentose) orketone group (keto- prefix, as in ketopentose). Classify glucoseand fructose in this way.arrow_forwardA reddish color is obtained when compound A (a disaccharide) is reacted with Benedict solution. Is this compound more likely maltose or sucrosearrow_forwardXylulose has the following structural formula. To what carbohydrate class does xylulose belong based on the number of carbons and carbonyl functionality? A) aldotetrose B) aldopentose C) ketotetrose D) ketopentose E) ketohexosearrow_forward
- The disaccharide lactose is built up by one D-galacto- and one D-gluco monosaccharide unit. Draw L-galactose in the Fischer projection (open) form and in its most stable pyranose ring conformation form and determine if the latter is a 1C4 or a 4C1 conformation.arrow_forwardDraw the structures (using chair conformations of pyranoses) of the following disaccharides. a-d-fructofuranosyl-b-d-mannopyranoside(arrow_forwardWhich of the following saccharides has INCORRECT paired description/s? * D-mannose: Monosaccharide: Prevents UTI Cellobiose: Disaccharide: With 2 glucose units Heparin: Acidic polysaccharide: Blood coagulant N-acetyl-galactosamine: Amino sugar: Present in type-A blood Keratin sulfate: Structural Polysaccharide: Most heterogenous GAGSarrow_forward
- Lactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactosearrow_forwardi need an answer pleaseeeearrow_forwardSuggest how you could distinguish a sample of glucose from a sample of maltose using Benedict’s reagent. [Hint: maltose is a disaccharide reducing sugar].arrow_forward
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