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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 73

Draw the Fischer projection of the product of reduction reaction of d-galactose at C1

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1
Identify the structure of D-galactose, which is an aldohexose with the aldehyde group at C1.
Understand that a reduction reaction at C1 will convert the aldehyde group to a primary alcohol group.
Draw the Fischer projection of D-galactose, ensuring the correct orientation of hydroxyl groups on C2, C3, C4, and C5.
Replace the aldehyde group at C1 with a CH2OH group to represent the reduction to an alcohol.
Ensure the stereochemistry of the remaining chiral centers (C2, C3, C4, C5) remains unchanged 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 indicate bonds that extend behind the plane.
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Reduction Reaction

A reduction reaction involves the gain of electrons or hydrogen atoms by a molecule, often resulting in the decrease of its oxidation state. In the context of carbohydrates, reduction typically refers to the conversion of an aldehyde or ketone group into an alcohol. For d-galactose, this means that the carbonyl group at C1 is reduced to a hydroxyl group, altering its structure and properties.
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D-Galactose

D-galactose is a monosaccharide, specifically an aldohexose, that plays a crucial role in various biological processes. It is an epimer of glucose, differing only in the configuration around one specific carbon atom. Understanding its structure is essential for predicting the outcome of chemical reactions, such as reduction, which modifies its functional groups and overall stereochemistry.
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