Textbook Question
D-Fructose can form a six-membered cyclic hemiacetal as well as the more prevalent five-membered cyclic form. Draw the α isomer of D-fructose in the six-membered ring.
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 68
Trehalose, a disaccharide found in the blood of insects, has the following structure. What simple sugars would you obtain on hydrolysis of trehalose? (Hint: Rotate one of the rings in your head or redraw it rotated.)
Verified step by step guidance1
Understand the problem: Hydrolysis of a disaccharide involves breaking the glycosidic bond between the two monosaccharide units. This process typically yields the two simple sugars that make up the disaccharide.
Examine the structure of trehalose: Trehalose is a disaccharide composed of two glucose molecules linked by an α,α-1,1-glycosidic bond. The hint suggests visualizing one of the rings rotated to better understand the linkage.
Identify the glycosidic bond: In trehalose, the glycosidic bond connects the anomeric carbons (C1) of both glucose units. This is an unusual linkage compared to other disaccharides like maltose or sucrose.
Predict the products of hydrolysis: When trehalose undergoes hydrolysis, the glycosidic bond is cleaved, resulting in two glucose molecules as the products. This reaction is typically catalyzed by an enzyme or acid.
Summarize the result: The simple sugars obtained from the hydrolysis of trehalose are two glucose molecules. This can be confirmed by analyzing the structure and the nature of the glycosidic bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Trehalose Structure
Trehalose is a disaccharide composed of two glucose molecules linked by an α,α-1,1-glycosidic bond. Understanding its structure is crucial for predicting the products of hydrolysis, as the specific linkage determines how the molecule can be broken down into simpler sugars.
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Hydrolysis Reaction
Hydrolysis is a chemical reaction that involves the breaking of a bond in a molecule using water. In the case of trehalose, hydrolysis will cleave the glycosidic bond, resulting in the formation of two monosaccharides, which are the simplest form of carbohydrates.
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Monosaccharides
Monosaccharides are the simplest form of carbohydrates, consisting of single sugar units. In the context of trehalose, hydrolysis yields two glucose molecules, which are key energy sources in biological systems and serve as building blocks for more complex carbohydrates.
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Related Practice
Textbook Question
Are the α and β forms of the disaccharide lactose enantiomers of each other? Why or why not?
Textbook Question
Describe the differences between mono-, di-, and polysaccharides.
Textbook Question
Amylose (a form of starch) and cellulose are both polymers of glucose. What is the main structural difference between them? What roles do these two polymers have in nature?
Textbook Question
How are amylose and amylopectin similar to each other, and how are they different from each other?
Textbook Question
Lactose and maltose are reducing disaccharides, but sucrose is a nonreducing disaccharide. Explain.