Textbook Question
Will the following carbohydrates produce a positive Benedict's test?
a. D-glucose
Ch.6 Carbohydrates Life's Sweet Molecules
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696
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Table of contents
- Ch.4 Introduction to Organic Compounds75
- Ch.5 Chemical Reactions19
- Ch.6 Carbohydrates Life's Sweet Molecules62
- Ch.7 States of Matter and Their Attractive Forces8
- Ch.8 Solution Chemistry Sugar and Water Do Mix4
- Ch.10 Proteins Workers of the Cell89
- Ch.11 Nucleic Acids Big Molecules with a Big Role69
- Ch.12 Food as Fuel An Overview of Metabolism65
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 77
Draw the product of the following 1→4 condensation and name the glycosidic bond:
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Identify the two monosaccharides involved in the reaction. A 1→4 condensation typically involves the hydroxyl group on the anomeric carbon (carbon 1) of one monosaccharide and the hydroxyl group on carbon 4 of the second monosaccharide.
Determine the orientation of the glycosidic bond. The bond can be either alpha (α) or beta (β), depending on the configuration of the anomeric carbon in the first monosaccharide. If the hydroxyl group on the anomeric carbon is pointing down, it is α; if it is pointing up, it is β.
Remove a molecule of water (H₂O) during the condensation reaction. This occurs as the hydroxyl group from the anomeric carbon of the first monosaccharide and the hydrogen from the hydroxyl group on carbon 4 of the second monosaccharide combine to form water.
Connect the remaining oxygen atom from the anomeric carbon of the first monosaccharide to carbon 4 of the second monosaccharide, forming the glycosidic bond. Represent this bond clearly in the product structure.
Name the glycosidic bond based on the configuration of the anomeric carbon (α or β) and the carbons involved in the linkage (1→4). For example, if the bond is α and connects carbon 1 of the first monosaccharide to carbon 4 of the second, it is called an α(1→4) glycosidic bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
1→4 Condensation Reaction
A 1→4 condensation reaction refers to the chemical process where two monosaccharides are linked together by a glycosidic bond, specifically between the first carbon of one sugar and the fourth carbon of another. This reaction releases a molecule of water and forms a disaccharide or oligosaccharide. Understanding this reaction is crucial for grasping how carbohydrates are synthesized in biological systems.
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Condensed Formula Concept 1
Glycosidic Bond
A glycosidic bond is a type of covalent bond that connects a carbohydrate (sugar) molecule to another group, which can be another carbohydrate or a different type of molecule. In the context of the 1→4 condensation, this bond specifically forms between the first carbon of one sugar and the fourth carbon of another, resulting in a specific linkage that defines the structure and properties of the resulting carbohydrate.
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Product Structure
The product structure resulting from a 1→4 condensation reaction is typically a disaccharide or oligosaccharide, depending on the number of monosaccharides involved. The specific arrangement of atoms and the type of glycosidic bond formed influence the physical and chemical properties of the carbohydrate, such as solubility and digestibility. Identifying the product structure is essential for understanding its biological function and applications.
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Related Practice
Textbook Question
Isomaltose, a disaccharide formed during caramelization in cooking, contains two glucose units bonded ⍺(1→6). Draw the structure of isomaltose.
Textbook Question
Our bodies cannot digest cellulose because we lack the enzyme cellulase. Why is cellulose an important part of a healthy diet if we cannot digest it?
Textbook Question
Will the following carbohydrates produce a positive Benedict’s test?
b. lactose
Textbook Question
The glycosidic bond in a disaccharide was determined to be α(1→6). Hydrolysis of the disaccharide produced one galactose and one fructose. Draw the structure of the disaccharide.
Textbook Question
Draw the Fischer projection of the product of reduction reaction of D-galactose at C1.