Textbook Question
How many stereoisomers are possible for b. an aldoheptose?
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Ch. 20 - The Organic Chemistry of Carbohydrates
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 21, Problem 14a,b
a. Name an aldohexose other than D-glucose that is oxidized to D-glucaric acid by nitric acid.
b. What is another name for D-glucaric acid?
Verified step by step guidance1
Step 1: Understand the problem. Part (a) asks for an aldohexose (a six-carbon sugar with an aldehyde group) other than D-glucose that can be oxidized to D-glucaric acid by nitric acid. Part (b) asks for an alternative name for D-glucaric acid.
Step 2: Recall the oxidation process. Nitric acid oxidizes both the aldehyde group at the C-1 position and the primary alcohol group at the C-6 position of an aldohexose to carboxylic acids, forming a dicarboxylic acid. This reaction is characteristic of aldohexoses.
Step 3: Identify another aldohexose. Besides D-glucose, other aldohexoses include D-mannose and D-galactose. These sugars also have the structural features necessary for oxidation by nitric acid to form dicarboxylic acids.
Step 4: Provide the alternative name for D-glucaric acid. D-glucaric acid is also known as saccharic acid. This name is derived from its relationship to sugars (saccharides).
Step 5: Summarize the findings. For part (a), D-mannose or D-galactose can be oxidized to D-glucaric acid by nitric acid. For part (b), the alternative name for D-glucaric acid is saccharic acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aldohexoses
Aldohexoses are six-carbon sugars that contain an aldehyde group. They are a subclass of monosaccharides characterized by their structure, which includes a carbonyl group at the first carbon and hydroxyl groups on the remaining carbons. Examples include glucose, galactose, and mannose. Understanding their structure is essential for recognizing their reactivity and potential oxidation products.
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Which aldohexoses produce the same Wohl Degradation product
Oxidation of Sugars
The oxidation of sugars involves the conversion of alcohol groups into carbonyl groups or carboxylic acids. In the case of aldohexoses, nitric acid can oxidize the aldehyde group and the primary alcohol group at the end of the sugar chain, leading to the formation of d-glucaric acid. This process is significant in organic chemistry as it illustrates the reactivity of carbohydrates and their transformation into different functional groups.
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D-Glucaric Acid
D-glucaric acid, also known as saccharic acid, is a dicarboxylic acid derived from the oxidation of aldohexoses. It contains two carboxylic acid groups, which result from the oxidation of both the aldehyde and the terminal alcohol of the sugar. This compound is important in biochemistry and can be involved in various metabolic pathways, making it relevant for understanding sugar metabolism and its derivatives.
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Related Practice
Textbook Question
What two monosaccharides can be degraded to
a. D-ribose?
Textbook Question
Name another pair of aldohexoses that are oxidized to identical aldaric acids.
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Textbook Question
What monosaccharides are formed in a modified Kiliani–Fischer synthesis starting with each of the following monosaccharides?
a. D-xylose
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Textbook Question
What monosaccharide is reduced to two alditols, one of which is the alditol obtained from the reduction of
1. D-talose?
2. D-allose?
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Textbook Question
When D-tagatose is added to a basic aqueous solution, an equilibrium mixture of monosaccharides is obtained, two of which are aldohexoses and two of which are ketohexoses. Identify the aldohexoses and ketohexoses.
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