Textbook Question
Suggest a synthesis of the following acylated sugars.
(b)
Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 26, Problem 34c
Predict the product of each of the following reactions.
(c) 
Verified step by step guidance1
Identify the functional groups present in the starting material. The molecule has an aldehyde group (CHO) and two alcohol groups (OH).
Recognize the reagent used in the reaction. Bromine in water (Br2, H2O) is typically used for the oxidation of aldehydes to carboxylic acids.
Understand the mechanism: Bromine water can oxidize the aldehyde group to a carboxylic acid. The reaction involves the formation of a bromohydrin intermediate, which is then hydrolyzed to form the carboxylic acid.
Predict the product: The aldehyde group (CHO) will be oxidized to a carboxylic acid group (COOH), while the alcohol groups remain unchanged.
Draw the structure of the product: The final product will have a carboxylic acid group in place of the aldehyde group, with the rest of the molecule remaining the same.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Weak Oxidation
Weak oxidation involves mild oxidizing agents like Br2 in water, which selectively oxidize aldehydes to carboxylic acids without affecting other functional groups. In the context of monosaccharides, this reaction targets the aldehyde group, converting it to a carboxylic acid, while leaving the rest of the molecule intact.
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Monosaccharides - Weak Oxidation (Aldonic Acid)
Aldehyde Functional Group
An aldehyde group is characterized by a carbon atom bonded to a hydrogen atom and double-bonded to an oxygen atom (CHO). In organic chemistry, aldehydes are reactive and can be oxidized to form carboxylic acids. Understanding the reactivity of aldehydes is crucial for predicting the outcome of oxidation reactions.
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02:36Identifying Functional Groups
Monosaccharide Structure
Monosaccharides are the simplest form of carbohydrates, consisting of a single sugar unit with multiple hydroxyl groups and an aldehyde or ketone group. The structure of a monosaccharide determines its reactivity and the type of chemical reactions it can undergo, such as oxidation of the aldehyde group in the presence of Br2 and H2O.
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Related Practice
Textbook Question
Suggest a synthesis of the following acylated sugars.
(a)
Textbook Question
Predict the product of each of the following reactions.
(b)
1
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Textbook Question
In each of the disaccharides shown (a–c), (i) identify the reducing end of the sugar, (ii) tell what monosaccharides are used to make it, and (iii) tell what type of glycoside linkage is present.
(a)
Textbook Question
Ketohexoses form from aldohexoses. Suggest a mechanism for the acid-catalyzed version of this reaction. What type of reaction is this? [You’ve seen it before.]
9
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Textbook Question
Predict the product of each of the following reactions.
(d)