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 28c
Name the following compounds and indicate whether or not each is a reducing sugar:
c. 
Verified step by step guidance1
Step 1: Analyze the structure of the compound. The image shows a five-membered ring with an oxygen atom incorporated into the ring, indicating that this is a furanose form of a sugar. Additionally, there are hydroxyl (-OH) groups and an ethyl group (-CH2CH3) attached to the ring.
Step 2: Identify the functional groups and substituents. The compound has a hydroxymethyl group (-CH2OH) attached to the ring, hydroxyl groups (-OH) on the ring, and an ethoxy group (-OCH2CH3) attached to the ring. These features suggest that the compound is a derivative of a sugar.
Step 3: Determine if the compound is a reducing sugar. Reducing sugars are characterized by the presence of a free anomeric carbon (a carbon attached to the oxygen in the ring and also to a hydroxyl group). In this structure, the anomeric carbon is bonded to an ethoxy group (-OCH2CH3), which means it is not free and cannot act as a reducing agent.
Step 4: Name the compound systematically. The base sugar is likely derived from ribose (a five-carbon sugar), but the ethoxy group substitution modifies the name. The compound can be named as ethyl β-D-ribofuranoside, where 'ethyl' indicates the ethoxy group and 'ribofuranoside' indicates the sugar derivative in the furanose form.
Step 5: Conclude the analysis. The compound is named ethyl β-D-ribofuranoside, and it is not a reducing sugar because the anomeric carbon is not free due to the ethoxy group substitution.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reducing Sugars
Reducing sugars are carbohydrates that can donate electrons to other molecules, typically due to the presence of a free aldehyde or ketone group. This property allows them to reduce certain chemical reagents, such as Benedict's or Fehling's solution, which is a key characteristic in identifying them. Common examples include glucose and fructose, which can participate in redox reactions.
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Reducing Sugars
Structural Representation of Sugars
Understanding the structural representation of sugars is crucial for identifying their functional groups. Sugars can exist in linear or cyclic forms, and their structure determines their reactivity. Recognizing whether a sugar has a free aldehyde or ketone group in its structure is essential for determining if it is a reducing sugar.
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02:21Reducing Sugars
Nomenclature of Organic Compounds
Nomenclature refers to the systematic naming of organic compounds based on established rules, such as those set by IUPAC. For sugars, this includes identifying the number of carbon atoms, the type of functional groups, and the stereochemistry. Proper nomenclature is vital for clear communication in organic chemistry and helps in understanding the properties and classifications of compounds.
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01:40Defining meso compounds.
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
Name the following compounds and indicate whether or not each is a reducing sugar:
a.
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Textbook Question
Why is only a trace amount of acid used in the formation of an N-glycoside?
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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
a. Identify the sugars in amygdalin.
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