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Ch.13 Carbohydrates
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 13, Problem 43

Indicate whether each disaccharide in Problem 13.41 is a reducing sugar or not.
a.
b. Chemical structure of a disaccharide, showing its molecular formula and hydroxyl groups for analysis of reducing sugars.

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1
Identify the disaccharides mentioned in Problem 13.41. Common examples of disaccharides include sucrose, lactose, and maltose. Each disaccharide's structure will determine whether it is a reducing sugar.
Understand the concept of a reducing sugar: A reducing sugar is a carbohydrate that can act as a reducing agent because it has a free aldehyde group (-CHO) or a free ketone group (-C=O) in its structure. This is typically determined by the presence of a free anomeric carbon that is not involved in a glycosidic bond.
Examine the structure of each disaccharide. Look for the anomeric carbon in each monosaccharide unit of the disaccharide. If the anomeric carbon of at least one monosaccharide is free (not involved in the glycosidic bond), the disaccharide is a reducing sugar.
For example, lactose and maltose are reducing sugars because they have a free anomeric carbon in one of their monosaccharide units. In contrast, sucrose is not a reducing sugar because both anomeric carbons are involved in the glycosidic bond, leaving no free aldehyde or ketone group.
Conclude whether each disaccharide in Problem 13.41 is a reducing sugar or not based on the analysis of their structures and the presence of a free anomeric carbon.

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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 solutions, which is a key characteristic in identifying them. Common examples include glucose and fructose, while sucrose is a non-reducing sugar.
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Disaccharides

Disaccharides are carbohydrates composed of two monosaccharide units linked by a glycosidic bond. They can be classified based on their reducing properties; some disaccharides, like maltose and lactose, contain a free anomeric carbon that can act as a reducing agent, while others, like sucrose, do not. Understanding the structure of disaccharides is essential for determining their reactivity.
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Glycosidic Bond

A glycosidic bond is a type of covalent bond that forms between the anomeric carbon of a sugar and a hydroxyl group of another molecule, which can be another sugar or a different type of compound. The formation of this bond can affect the reducing properties of the sugar; if the bond involves the anomeric carbon of one sugar, it may prevent the sugar from acting as a reducing agent. This concept is crucial for analyzing the reducing nature of disaccharides.
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