Textbook Question
b. Identify the glycosidic linkage that connects the sugars.
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Ch. 20 - The Organic Chemistry of Carbohydrates
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 21, Problem 30a
a. Identify the sugars in amygdalin.
Verified step by step guidance1
Understand the structure of amygdalin: Amygdalin is a glycoside composed of a cyanogenic aglycone (benzaldehyde cyanohydrin) and two sugar units. The sugars are attached to the aglycone via glycosidic bonds.
Break down the glycosidic bonds: Amygdalin contains two sugar units, which can be identified by analyzing the structure of the molecule. These sugars are typically glucose and another sugar.
Identify the first sugar: The first sugar in amygdalin is a β-D-glucose unit. This can be determined by examining the stereochemistry and connectivity of the sugar moiety in the molecule.
Identify the second sugar: The second sugar in amygdalin is a β-D-glucose unit as well. It is connected to the first glucose via a glycosidic bond, forming a disaccharide structure.
Conclude the sugar identification: The sugars in amygdalin are two β-D-glucose units. This conclusion is based on the structural analysis of the molecule and the known composition of amygdalin.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amygdalin Structure
Amygdalin is a cyanogenic glycoside composed of a benzene ring, a sugar moiety, and a nitrile group. Understanding its structure is crucial for identifying the specific sugars present. The sugar component is typically a disaccharide, which is essential for the biological activity of amygdalin.
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Cyanogenic Glycosides
Cyanogenic glycosides are plant compounds that can release cyanide when hydrolyzed. Amygdalin is one of the most well-known examples, and recognizing its classification helps in understanding its potential toxicity and the sugars involved in its structure. This knowledge is important for studying plant biochemistry and toxicology.
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Monosaccharides and Disaccharides
Sugars can be classified as monosaccharides (single sugar units) or disaccharides (two sugar units linked together). In the case of amygdalin, the sugar component is a disaccharide made up of glucose and another sugar, typically mandelonitrile. Familiarity with these classifications aids in identifying the specific sugars present in various compounds.
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Related Practice
Textbook Question
Name the following compounds and indicate whether or not each is a reducing sugar:
b.
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Textbook Question
What is the main structural difference between a. amylose and cellulose?
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Textbook Question
Name the following compounds and indicate whether or not each is a reducing sugar:
c.
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Textbook Question
What is the specific rotation of an equilibrium mixture of fructose? (Hint: Recall that the specific rotation of an equilibrium mixture of glucose is +52.7.)
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Textbook Question
What is the main structural difference between b. amylose and amylopectin?
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