Textbook Question
Name the epimers of D-glucose.
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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 34e
What product or products are obtained when D-galactose reacts with each of the following?
e. Br2 in water
Verified step by step guidance1
Identify the functional groups present in d-galactose. D-galactose is an aldose sugar, meaning it contains an aldehyde group (-CHO) at the anomeric carbon (C1) and hydroxyl groups (-OH) on the other carbons.
Understand the reactivity of Br2 in water. Bromine in water is a mild oxidizing agent that selectively oxidizes aldehydes to carboxylic acids without affecting other functional groups like alcohols.
Focus on the aldehyde group in d-galactose. The aldehyde group at C1 will be oxidized to a carboxylic acid group (-COOH), converting d-galactose into d-galactonic acid.
Note that the hydroxyl groups on the other carbons of d-galactose remain unchanged during this reaction because Br2 in water does not oxidize alcohols under these conditions.
Conclude that the product of the reaction is d-galactonic acid, which is the oxidized form of d-galactose where the aldehyde group has been converted to a carboxylic acid group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Sugars
The reaction of sugars like d-galactose with oxidizing agents, such as Br2 in water, leads to the oxidation of the hydroxyl groups. This process can convert the aldehyde or alcohol functional groups into carboxylic acids or other oxidized forms, depending on the conditions and the specific sugar structure.
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Reducing Sugars
D-Galactose Structure
D-galactose is a six-carbon aldose sugar with a specific stereochemistry. Understanding its structure, including the arrangement of hydroxyl groups and the aldehyde functional group, is crucial for predicting the products of its reactions, particularly how it interacts with oxidizing agents.
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Halogenation Reactions
Halogenation involves the introduction of halogen atoms into organic compounds. In the case of d-galactose reacting with Br2 in water, the reaction can lead to the formation of brominated products, which may include oxidized forms of the sugar, highlighting the importance of understanding reaction mechanisms in organic chemistry.
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Related Practice
Textbook Question
What product or products are obtained when D-galactose reacts with each of the following?
f. ethanol + HCl
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Textbook Question
What product or products are obtained when D-galactose reacts with each of the following?
b. Ag+, NH3, HO-
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Textbook Question
What product or products are obtained when d-galactose reacts with each of the following?
g.
1. hydroxylamine/trace acid
2. acetic anhydride/∆
3. HO-/H2O
Textbook Question
What product or products are obtained when d-galactose reacts with each of the following?
d. excess CH3I + Ag2O
Textbook Question
What product or products are obtained when D-galactose reacts with each of the following?
c. NaBH4, followed by H3O+
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