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 34d
Predict the product of each of the following reactions.
(d) 
Verified step by step guidance1
Identify the starting material: The structure shown is a sugar molecule, specifically a hexose, with a carboxylic acid group at the top and a primary alcohol group at the bottom.
Recognize the reagents: The reaction involves ferric sulfate (Fe2(SO4)3) and hydrogen peroxide (H2O2). This combination is often used as an oxidizing agent.
Determine the likely reaction: Given the presence of an oxidizing agent, the primary alcohol group at the bottom of the sugar molecule is likely to be oxidized to a carboxylic acid.
Predict the product: The oxidation of the primary alcohol group will result in the formation of a dicarboxylic acid, where both the top and bottom of the sugar molecule have carboxylic acid groups.
Consider stereochemistry: Ensure that the stereochemistry of the sugar molecule is maintained in the product, as the oxidation reaction does not affect the stereocenters in the middle of the molecule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ruff Degradation
Ruff degradation is a chemical reaction used to shorten the carbon chain of aldoses by one carbon atom. It involves the oxidation of the aldose to an aldonic acid, followed by decarboxylation. In this reaction, the aldonic acid is treated with hydrogen peroxide and ferric sulfate, leading to the removal of the terminal carboxyl group as carbon dioxide, thus shortening the sugar by one carbon.
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Aldonic Acids
Aldonic acids are a type of sugar acid derived from aldoses, where the aldehyde group is oxidized to a carboxylic acid. In the context of Ruff degradation, the aldose is first converted into an aldonic acid before decarboxylation occurs. This transformation is crucial as it sets the stage for the subsequent removal of the carboxyl group, facilitating the shortening of the carbon chain.
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Decarboxylation
Decarboxylation is a chemical reaction that involves the removal of a carboxyl group, releasing carbon dioxide. In Ruff degradation, decarboxylation is the key step that results in the shortening of the sugar's carbon chain. The reaction conditions, including the presence of hydrogen peroxide and ferric sulfate, facilitate the decarboxylation of the aldonic acid, leading to the formation of a sugar with one less carbon atom.
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Related Practice
Textbook Question
Predict the product of each of the following reactions.
(b)
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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.]
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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.
(b)
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Textbook Question
Predict the product of each of the following reactions.
(c)
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