Textbook Question
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(b) H2 , Ni (partial hydrogenation)
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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 40
Maltose, like cellobiose, is composed of two glucose units. What is the difference between maltose and cellobiose?
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Identify the structure of maltose: Maltose is a disaccharide composed of two glucose units linked by an α(1→4) glycosidic bond. This means the first glucose unit is in the alpha configuration at the anomeric carbon, and it is connected to the fourth carbon of the second glucose unit.
Identify the structure of cellobiose: Cellobiose is also a disaccharide composed of two glucose units, but they are linked by a β(1→4) glycosidic bond. This means the first glucose unit is in the beta configuration at the anomeric carbon, and it is connected to the fourth carbon of the second glucose unit.
Compare the glycosidic linkages: The key difference between maltose and cellobiose lies in the type of glycosidic bond. Maltose has an α(1→4) linkage, while cellobiose has a β(1→4) linkage.
Understand the implications of the linkage difference: The α and β configurations affect the three-dimensional structure and properties of the disaccharides. The alpha linkage in maltose results in a different orientation compared to the beta linkage in cellobiose, which can affect how these sugars are digested and utilized by organisms.
Summarize the difference: The primary difference between maltose and cellobiose is the configuration of the glycosidic bond between the glucose units: maltose has an α(1→4) linkage, while cellobiose has a β(1→4) linkage.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Glycosidic Bond
A glycosidic bond is a type of covalent bond that connects two monosaccharides, forming a disaccharide. The bond is formed through a dehydration reaction, where a water molecule is released. The specific type of glycosidic bond (α or β) determines the properties and digestibility of the resulting sugar.
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Single bonds, double bonds, and triple bonds.
Maltose Structure
Maltose is a disaccharide composed of two glucose units linked by an α(1→4) glycosidic bond. This structure allows maltose to be easily broken down by enzymes like maltase, making it a readily available source of energy. Maltose is commonly found in malted foods and beverages.
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Cellobiose Structure
Cellobiose is also a disaccharide made up of two glucose units, but they are connected by a β(1→4) glycosidic bond. This structural difference makes cellobiose resistant to hydrolysis by human digestive enzymes, as it is primarily found in cellulose, a major component of plant cell walls.
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Related Practice
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)
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Textbook Question
Draw a mechanism for the acid-catalyzed, nonenzymatic conversion of DPP to IPP. How do you know your mechanism is correct?
418
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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.]
1093
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Textbook Question
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(a) H2 , Pd
1015
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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)
400
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