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Chapter 13: Problem 37
Draw the Fischer projection for the oxidation and the reduction products of\(\mathrm{D}\) -xylose. What are the names of the sugar acid and the sugaralcohol produced?
Short Answer
Expert verified
The sugar acid is D-xylonic acid and the sugar alcohol is xylitol.
Step by step solution
01
Understand \(\text{D}\)-xylose Structure
First, recognize that \(\text{D}\)-xylose is a five-carbon aldose with the following structure in Fischer projection: \[\text{CHO-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH}\]
02
Oxidation to Sugar Acid
In oxidation, the aldehyde group (\(\text{CHO}\)) at the top of the Fischer projection of \(\text{D}\)-xylose is converted to a carboxylic acid group (\(\text{COOH}\)). The resulting sugar acid is known as D-xylonic acid. The Fischer projection of D-xylonic acid is: \[\text{COOH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH}\]
03
Reduction to Sugar Alcohol
In reduction, the aldehyde group (\(\text{CHO}\)) at the top of the Fischer projection of \(\text{D}\)-xylose is converted to an alcohol group (\(\text{CH}_2\text{OH}\)). The resulting sugar alcohol is known as xylitol. The Fischer projection of xylitol is: \[\text{CH}_2\text{OH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH}\]
04
Naming the Compounds
The sugar acid produced from the oxidation of \(\text{D}\)-xylose is called D-xylonic acid. The sugar alcohol produced from the reduction is called xylitol.
Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Fischer Projection
The Fischer projection is a two-dimensional representation often used to depict carbohydrates. In this projection, the molecule is drawn vertically with the carbon chain running from top to bottom. The horizontal lines represent bonds coming out of the plane towards the viewer, while vertical lines indicate bonds going into the plane. For example, \(\text{D-xylose}\) in Fischer projection can be represented as:
\[ \text{CHO-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH} \]
This projection helps in visualizing stereochemistry, which is vital for understanding how sugars behave chemically.
Sugar Acid
Sugar acids are derived from monosaccharides (simple sugars) where the aldehyde group (\(\text{CHO}\)) is oxidized to a carboxyl group (\(\text{COOH}\)). This transformation typically occurs at the carbon that originally carried the aldehyde group. For \(\text{D-xylose}\), this conversion gives \(\text{D-xylonic acid}\). The Fischer projection for \(\text{D-xylonic acid}\) looks like:
\[ \text{COOH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH} \]
Sugar acids like D-xylonic acid are important in various biochemical pathways and can be used to synthesize other bioactive molecules.
Sugar Alcohol
Sugar alcohols are formed by the reduction of the carbonyl group (aldehyde) in monosaccharides to a hydroxyl (alcohol) group. For \(\text{D-xylose}\), reduction leads to the formation of xylitol. The Fischer projection for xylitol is:
\[ \text{CH}_2\text{OH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH} \]
Sugar alcohols like xylitol are often used as low-calorie sweeteners in various food products because they provide sweetness similar to sugar but with fewer calories.
D-xylonic Acid
D-xylonic acid is the product of the oxidation of \(\text{D-xylose}\). During oxidation, \(\text{D-xylose}\) undergoes a transformation where its aldehyde group turns into a carboxyl group. This changes its chemical properties and makes D-xylonic acid a sugar acid. The structure of D-xylonic acid in the Fischer projection is:
\[ \text{COOH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH} \]
This acid plays a role in various metabolic processes and can be synthesized or utilized in different biochemical pathways.
Xylitol
Xylitol is the sugar alcohol derived from the reduction of \(\text{D-xylose}\). In this reduction, the aldehyde group on \(\text{D-xylose}\) is converted to a hydroxyl group, making it a polyol. The Fischer projection for xylitol is:
\[ \text{CH}_2\text{OH-CH(OH)-CH(OH)-CH(OH)-CH}_2\text{OH} \]
Xylitol is widely used as a sugar substitute due to its sweet taste and lower calorie content. Additionally, it has dental benefits as it is not easily fermented by oral bacteria, thus reducing the risk of cavities.
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