Chapter 20: Problem 29
What functional groups are present in the simple sugars (monosaccharides)?
Short Answer
Expert verified
The functional groups present in monosaccharides are carbonyl groups (C=O), which can be an aldehyde group (R-CHO) in aldoses or a ketone group (R-CO-R') in ketoses, and hydroxyl groups (OH) on every other carbon in the molecule.
Step by step solution
01
The General Structure of Monosaccharides
Monosaccharides are the simplest form of sugars and are carbohydrates that cannot be broken down into simpler units. They contain a single unit of sugar and have the general formula \((CH_2O)_n\), where n is usually between 3 to 7. Monosaccharides have a carbon backbone and are classified based on the number of carbon atoms in the molecule, such as trioses (n=3), tetroses (n=4), pentoses (n=5), hexoses (n=6), and heptoses (n=7). They can form different isomers depending on the arrangements of the functional groups.
02
Identifying Functional Groups in Monosaccharides
In monosaccharides, there are two main functional groups present:
1. Carbonyl group (C=O): This functional group determines if the monosaccharide is an aldose or a ketose. An aldose has an aldehyde group (R-CHO) as the carbonyl group, while a ketose has a ketone group (R-CO-R') as the carbonyl group. In the monosaccharide, the carbonyl group is at the end of the carbon backbone for an aldose and at the second carbon atom from the end for a ketose.
2. Hydroxyl group (OH): A hydroxyl group is present on every other carbon in the monosaccharide backbone, which are called alcohol groups. This group plays a significant role in the formation of glycosidic linkages in complex carbohydrates and is also involved in crucial reactions like the formation of hemiacetals and hemiketals.
03
Examples of Monosaccharides and Functional Groups
Let's look at some examples of monosaccharides and their functional groups:
- Glucose (\(C_6H_{12}O_6\)) is a hexose and is an aldose sugar due to the presence of an aldehyde group as the carbonyl group. It also has five hydroxyl groups, one attached to each of the other carbon atoms in the structure.
- Fructose (\(C_6H_{12}O_6\)) is also a hexose but is a ketose sugar due to the presence of a ketone group as the carbonyl group. It also has five hydroxyl groups, one attached to each of the other carbon atoms in the structure.
In conclusion, the functional groups present in monosaccharides are carbonyl groups (either aldehyde or ketone) and hydroxyl groups.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Carbonyl Group
In the world of monosaccharides, the carbonyl group is a defining feature. This group is represented by a carbon atom double-bonded to an oxygen atom (\(C=O\)). It is a critical functional group as it determines the type of monosaccharide - either an aldose or a ketose.
- Aldoses: These monosaccharides contain an aldehyde group. This means the carbonyl group is positioned at the end of the carbon chain, denoted as R-CHO.
- Ketoses: These monosaccharides feature a ketone group. Here, the carbonyl group is located on the second carbon, indicated as R-CO-R'.
Hydroxyl Group
Hydroxyl groups are the versatile sidekicks of the carbonyl group within monosaccharides. Each hydroxyl group consists of an oxygen and hydrogen atom bonded together (\(OH\)). These groups are attached to every other carbon in the carbon backbone of the monosaccharide.One of the fascinating roles of hydroxyl groups is in the formation of glycosidic linkages, which connect monosaccharides into complex carbohydrates like starch and cellulose. They are also pivotal in reactions that lead to the formation of hemiacetals and hemiketals.
- Every monosaccharide has multiple hydroxyl groups, significantly impacting its solubility and chemical behavior.
- The orientation of hydroxyl groups around the carbon chain contributes to the chirality of the molecule, affecting its interaction with other molecules.
Aldose and Ketose Classification
Classifying monosaccharides as aldoses or ketoses is based on the position of their carbonyl group. This classification is fundamental in understanding the behavior and function of these sugars in biological and chemical systems.
- Aldoses: These are sugars with the carbonyl group in the form of an aldehyde (R-CHO). Glucose is a prime example, with its aldehyde group placed at the end of its carbon chain. Being an aldose affects how glucose participates in metabolic processes like glycolysis.
- Ketoses: These sugars contain a ketone group (R-CO-R'). Fructose fits into this category, with its carbonyl located internally on the second carbon. This classification influences fructose's role in pathways like fructolysis.