Draw the Fischer projection for the oxidation and the reduction products of D-xylose. What are the names of the sugar acid and the sugar alcohol produced?

Verified step by step guidance

1. Understand the structure of D-xylose: D-xylose is a five-carbon aldose sugar (a monosaccharide with an aldehyde group). Its Fischer projection shows the arrangement of hydroxyl (-OH) groups and hydrogen atoms around the chiral carbons.
2. Oxidation of D-xylose: When D-xylose undergoes oxidation, the aldehyde group (-CHO) at the top of the Fischer projection is converted into a carboxylic acid group (-COOH). This forms a sugar acid. Draw the Fischer projection by replacing the aldehyde group with a carboxylic acid group while keeping the rest of the structure unchanged.
3. Reduction of D-xylose: When D-xylose undergoes reduction, the aldehyde group (-CHO) is converted into a primary alcohol group (-CH2OH). This forms a sugar alcohol. Draw the Fischer projection by replacing the aldehyde group with a primary alcohol group while keeping the rest of the structure unchanged.
4. Name the sugar acid: The sugar acid formed from the oxidation of D-xylose is called D-xylonic acid. This name reflects the conversion of the aldehyde group into a carboxylic acid group.
5. Name the sugar alcohol: The sugar alcohol formed from the reduction of D-xylose is called D-xylitol. This name reflects the conversion of the aldehyde group into a primary alcohol group.

Key Concepts

Fischer Projection

The Fischer projection is a two-dimensional representation of a molecule, particularly useful for depicting the stereochemistry of carbohydrates. In this format, the carbon skeleton is arranged vertically, with the most oxidized carbon at the top. Horizontal lines represent bonds that project out of the plane towards the viewer, while vertical lines represent bonds that extend behind the plane. This method is essential for visualizing the structure of sugars like D-xylose and understanding their stereoisomers.

Oxidation and Reduction in Sugars

Oxidation and reduction are chemical reactions that involve the transfer of electrons. In the context of sugars, oxidation typically refers to the conversion of an alcohol group (-OH) to a carbonyl group (C=O), resulting in the formation of sugar acids. Conversely, reduction involves the addition of electrons, often converting a carbonyl group back to an alcohol, leading to the formation of sugar alcohols. Understanding these processes is crucial for identifying the products of D-xylose.

Sugar Acid and Sugar Alcohol

Sugar acids and sugar alcohols are derivatives of carbohydrates formed through oxidation and reduction, respectively. A sugar acid, such as D-xylose's oxidation product, is characterized by the presence of a carboxylic acid group (-COOH), while a sugar alcohol, like the reduction product, contains multiple hydroxyl groups (-OH) and no carbonyl groups. Recognizing these compounds is important for understanding the biochemical pathways and applications of sugars in various contexts.