Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 22, Problem 4Q
Interpretation Introduction
Interpretation:
The structural formulas of the products (a), (b), (c), and (d) in the given reaction are to be determined.
Concept introduction:
Oxidation of aldoses by nitric acid produces optically inactive aldaric acids. This is due to the formation of meso compounds.
Ruff degradation reaction is used for decreasing the number of carbon atoms of the respective aldoses, thereby, shortening the carbon chain of the compound.
Fischer projection is a way of representing structures of
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Chapter 22 Solutions
Organic Chemistry
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...Ch. 22 - Prob. 1QCh. 22 - Prob. 2QCh. 22 - Give the structural formula of the monosaccharide...Ch. 22 - Prob. 4QCh. 22 - Prob. 5QCh. 22 - Prob. 6QCh. 22 - Prob. 7QCh. 22 - Prob. 8QCh. 22 - Select the reagent needed to perform the following...
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- Monosaccharides are cyclic hemiacetals that can react with alcohols to form acetals. The bond between the anomeric carbon atom of the monosaccharide and the oxygen atom of the -OR group is called a glycosidic bond. The name of the linkage contains the designation alpha (a) or beta (B) (from the anomeric carbon in the glycosidic bond) and the carbon numbers for the carbons from the two sugars. For this example, the linkage is an a-1,4 glycosidic bond. Н НО HO اب تاب است H OH H OH -OH Н Н OH H + OH HO a anomer CH₂OH H Н H О OH H2C OH Н H Classify the glycosidic linkage in the disaccharide. Н OH Н H OH OH OH - HO Н H HO OH OH Н CH₂OH H -OH H OH он H H -OH Н OH an a glycosidic bond Н OH + H2O о о о о В-1,6 a-1,6 a-1,1 B-1,5 I DON'T KNOW YET submitarrow_forwardSuppose you have two simple sugars, D-arabinose and L-tagatose. Both sugars cyclize and form a non-reducing disaccharide with the glycosidic bond oriented in the alpha position relative to each monosaccharide's structure. Give the full biochemical name for this disaccharide.arrow_forwardis this monosaccharide aldose or ketose? what is the chemical group and its location that allows its classification.arrow_forward
- A) Define "reducing sugar." (b) Sucrose is a disaccharide composed of glucose and fructose (Glc(1 → 2)Fru). Explain why sucrose is not a reducing sugar, even though both glucose and fructose are.arrow_forwardTwo molecules of glucose, a monosaccharide, when joined together they form a molecule of maltose. Write a chemical reaction to show this process.arrow_forward(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_forward
- Consider N-acetyl-d-glucosamine Q.) Draw a chair conformation for the disaccharide formed by joining two units of the pyranose form of N-acetyl-d-glucosamine by a b-1,4-glycosidic bond. If you draw this correctly, you have the structural formula for the repeating dimer of chitin, the structural polysaccharide component of the shell of lobsters and other crustaceans.arrow_forwardMonosaccharides 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 trisaccharide obtained from the partial hydrolysis of amylopectin showed two glycosidic linkages. A. Draw the structure of the trisaccharide B. If the trisaccharide is to be exhaustively methylated and subsequently hydrolyzed with an acid, how many different methylated products will be obtained? Draw their structures. C. Can an aqueous solution of the trisaccharide precipitate Cu as Cu2O? If it can, encircle the potential carbonyl carbon(s) in the trisaccharide. D. Can the trisaccharide exist in different anomeric forms? If yes, draw their structures.arrow_forward
- starch has free hemiacetal bonds it is non reducing sugar, explain ?arrow_forward(A) Identify the glycosidic bond in the following disaccharide (B) Decide whether the compound is a non reducing or reducing sugar (C) Polysaccharide units are usually bonded together with alpha or beta 1,6 or 1,4 linkages. What linkage is used in the disaccharide shown below?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
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