Textbook Question
What product or products are obtained when D-galactose reacts with each of the following?
e. Br2 in water
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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 34b
What product or products are obtained when D-galactose reacts with each of the following?
b. Ag+, NH3, HO-
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 and multiple hydroxyl (-OH) groups.
Understand the reaction conditions. The reagents Ag+, NH3, and HO- together form Tollens' reagent, which is commonly used to oxidize aldehydes to carboxylic acids.
Recognize the specific reaction mechanism. Tollens' reagent oxidizes the aldehyde group (-CHO) in d-galactose to a carboxylate group (-COO⁻), forming the corresponding aldonic acid (in this case, d-galactonic acid).
Write the chemical equation for the reaction. The aldehyde group of d-galactose reacts with Tollens' reagent, resulting in the formation of d-galactonic acid and the reduction of Ag+ to metallic silver (Ag⁰).
Conclude that the product of this reaction is d-galactonic acid, and metallic silver is deposited as a byproduct. The hydroxyl groups on the sugar remain unchanged during this reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
D-Galactose Structure
D-galactose is a monosaccharide with an aldehyde group and multiple hydroxyl groups. It is an aldohexose, meaning it contains six carbon atoms and an aldehyde functional group at one end. Understanding its structure is crucial for predicting its reactivity in chemical reactions, particularly in oxidation and reduction processes.
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Oxidation-Reduction Reactions
In organic chemistry, oxidation-reduction (redox) reactions involve the transfer of electrons between species. In the context of D-galactose reacting with Ag+ (silver ion), the aldehyde group can be oxidized to a carboxylic acid, while Ag+ is reduced to metallic silver. This transformation is essential for understanding the products formed in the reaction.
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Complex Formation with Ammonia
Ammonia (NH3) can react with carbonyl compounds, such as the aldehyde in D-galactose, to form imines or amines. This reaction is significant in organic synthesis and can lead to the formation of various nitrogen-containing products. Recognizing how ammonia interacts with sugars is key to predicting the outcome of the reaction in question.
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Related Practice
Textbook Question
Refer to Figure 20.5 to answer the following questions: b. People with type AB blood can receive blood from anyone, but they cannot give blood to everyone. To whom can they not give blood?
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Textbook Question
Refer to Figure 20.5 to answer the following questions: a. People with type O blood can donate blood to anyone, but they cannot receive blood from everyone. From whom can they not receive blood?
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Textbook Question
What product or products are obtained when d-galactose reacts with each of the following?
d. excess CH3I + Ag2O
803
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Textbook Question
What product or products are obtained when D-galactose reacts with each of the following?
c. NaBH4, followed by H3O+
1201
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Textbook Question
Explain why the C-3 OH group of vitamin C is more acidic than the C-2 OH group.
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