Textbook Question
Look at the open-chain form of D-mannose and draw the two glycosidic products that you expect to obtain by reacting D-mannose with methanol.
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Ch.20 Carbohydrates
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 20, Problem 55
Oxidation of the aldehyde group of ribose yields a carboxylic acid. Draw the structure of ribonic acid.
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Understand the problem: The oxidation of an aldehyde group (-CHO) in a sugar like ribose converts it into a carboxylic acid group (-COOH). This process forms a sugar acid, specifically ribonic acid in this case.
Start with the structure of ribose: Ribose is a five-carbon sugar (a pentose) with the molecular formula C₅H₁₀O₅. It contains an aldehyde group (-CHO) at the first carbon (C1) and hydroxyl groups (-OH) attached to the other carbons.
Identify the site of oxidation: The aldehyde group (-CHO) at the first carbon (C1) is the functional group that will be oxidized. Oxidation of an aldehyde involves the addition of an oxygen atom, converting it into a carboxylic acid group (-COOH).
Modify the structure: Replace the aldehyde group (-CHO) at C1 of ribose with a carboxylic acid group (-COOH). The rest of the ribose structure, including the hydroxyl groups on the other carbons, remains unchanged.
Draw the final structure: The resulting molecule, ribonic acid, will have the following structure: a carboxylic acid group (-COOH) at C1, hydroxyl groups (-OH) on C2, C3, and C4, and a primary alcohol (-CH₂OH) at C5. Ensure the stereochemistry of the hydroxyl groups matches that of ribose.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aldehyde Functional Group
An aldehyde is a functional group characterized by a carbon atom bonded to a hydrogen atom and a double bond to an oxygen atom (C=O). In ribose, the aldehyde group is located at the first carbon, making it an aldopentose. Understanding this structure is crucial for recognizing how oxidation can transform the aldehyde into a carboxylic acid.
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Oxidation Reaction
Oxidation is a chemical reaction that involves the loss of electrons or an increase in oxidation state. In the context of ribose, the oxidation of the aldehyde group results in the formation of a carboxylic acid, specifically ribonic acid. This transformation is essential for understanding how carbohydrates can be modified and their functional implications in biochemistry.
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Carboxylic Acid Structure
Carboxylic acids are organic compounds that contain a carboxyl group (-COOH), which consists of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group (OH). In ribonic acid, the carboxylic acid group replaces the aldehyde group of ribose, altering its chemical properties and reactivity. Recognizing this structure is vital for drawing the correct molecular representation of ribonic acid.
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Related Practice
Textbook Question
Reduction of D-fructose with a reducing agent yields a mixture of D-sorbitol along with a second, isomeric product. What is the structure of the second product?
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Textbook Question
Treatment of D-glucose with a reducing agent yields sorbitol, a substance used as a sugar substitute by people with diabetes. Draw the structure of sorbitol.
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Textbook Question
Treatment of an aldose with an oxidizing agent such as Tollens’ reagent yields a carboxylic acid. Gluconic acid, the product of glucose oxidation, is used as its magnesium salt for the treatment of magnesium deficiency. Draw the structure of gluconic acid.
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Textbook Question
Draw a disaccharide of two cyclic mannose molecules attached by an α-1,4 glycosidic linkage. Explain why the glycosidic products in Problem 20.58 are not reducing sugars, but the product in this problem is a reducing sugar.
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Textbook Question
Lactose and maltose are reducing disaccharides, but sucrose is a nonreducing disaccharide. Explain.
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