Textbook Question
What two monosaccharides can be degraded to
b. D-arabinose?
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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 14c
Name another pair of aldohexoses that are oxidized to identical aldaric acids.
Verified step by step guidance1
Understand the problem: Aldohexoses are six-carbon sugars with an aldehyde group. When oxidized, both the aldehyde group at C-1 and the primary alcohol group at C-6 are converted into carboxylic acids, forming aldaric acids. The task is to identify a pair of aldohexoses that yield the same aldaric acid upon oxidation.
Recall the concept of stereoisomers: Aldohexoses can have different configurations at their chiral centers (C-2, C-3, C-4, and C-5). Two aldohexoses that differ only in the configuration of their non-terminal chiral centers (C-2, C-3, C-4, or C-5) are called epimers. Epimers at C-2, C-3, or C-4 can sometimes yield the same aldaric acid upon oxidation.
Identify the key property: When oxidized, the stereochemistry at the non-terminal chiral centers (C-2, C-3, C-4, and C-5) determines whether two aldohexoses produce the same aldaric acid. If the stereochemistry of the two sugars is symmetric about the central carbon (C-3), they will yield the same aldaric acid.
Apply the concept to specific aldohexoses: For example, D-mannose and D-gulose are epimers at C-2 and C-3, respectively. Their stereochemistry is symmetric about C-3, so they are oxidized to the same aldaric acid.
Verify the result: Draw the Fischer projections of the two aldohexoses and their corresponding aldaric acid. Confirm that the aldaric acid has identical stereochemistry regardless of which aldohexose is oxidized.
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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 and include common sugars like glucose and galactose. The structure of aldohexoses allows them to undergo various chemical reactions, including oxidation, which is crucial for understanding their reactivity and transformations.
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Which aldohexoses produce the same Wohl Degradation product
Oxidation of Sugars
Oxidation in organic chemistry refers to the process where a molecule loses electrons, often involving the conversion of an aldehyde group to a carboxylic acid. In the context of aldohexoses, this reaction can lead to the formation of aldaric acids, which are dicarboxylic acids derived from the oxidation of both the aldehyde and the primary alcohol groups present in the sugar.
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Aldaric Acids
Aldaric acids are dicarboxylic acids formed from the oxidation of both the aldehyde and the terminal alcohol functional groups of aldohexoses. They have the general formula HOOC-(CHOH)n-COOH, where n is the number of carbon atoms between the two carboxylic acid groups. Identifying pairs of aldohexoses that yield the same aldaric acid upon oxidation is essential for understanding their structural similarities and reactivity.
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Related Practice
Textbook Question
What two monosaccharides can be degraded to
a. D-ribose?
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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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Textbook Question
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?
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