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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 6.71

Draw the Fischer projection of the product of the oxidation of d-galactose at C1.

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1
Identify the structure of D-galactose. D-galactose is an aldohexose, which means it has an aldehyde group at C1 and a total of six carbon atoms.
Understand that oxidation at C1 of an aldose like D-galactose converts the aldehyde group into a carboxylic acid group, forming an aldonic acid. In this case, D-galactose will be oxidized to D-galactonic acid.
Draw the Fischer projection of D-galactose, which is a vertical representation with the most oxidized carbon (C1) at the top. The hydroxyl groups on the right and left determine the D or L configuration.
Modify the Fischer projection of D-galactose by changing the aldehyde group at C1 to a carboxylic acid group (COOH) to represent D-galactonic acid.
Ensure that the stereochemistry at each chiral center (C2 to C5) remains unchanged from the original D-galactose structure in the Fischer projection.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Fischer Projection

The Fischer projection is a two-dimensional representation of a three-dimensional organic molecule, particularly useful for depicting carbohydrates. In this format, the carbon chain 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.
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Fischer Projections Example 1

Oxidation of Sugars

Oxidation of sugars involves the loss of electrons or an increase in oxidation state, often resulting in the formation of aldehydes or ketones. In the case of d-galactose, oxidation at C1 typically converts the aldehyde group into a carboxylic acid, leading to the formation of d-galactonic acid. Understanding this process is crucial for accurately drawing the product in its Fischer projection.
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Ketoses as Reducing Sugars Example 2

D-Galactose Structure

D-galactose is a six-carbon aldose sugar with a specific stereochemistry that influences its reactivity and properties. It has four chiral centers, and its configuration at these centers determines its biological function and interactions. Recognizing the structure of d-galactose is essential for predicting the outcome of its oxidation and accurately representing the resulting product.
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D vs L Enantiomers Example 1