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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 15

Classify structures A, B, and C in the figure as being either an enantiomer or a diastereomer of d-galactose.


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Identify the structure of D-galactose, which is a monosaccharide with a specific configuration of hydroxyl groups on its chiral centers.
Compare each structure (A, B, and C) to D-galactose by examining the configuration of each chiral center.
Determine if the structures are mirror images of D-galactose. If they are, they are enantiomers.
If the structures are not mirror images but have different configurations at one or more chiral centers, classify them as diastereomers.
Summarize the classification of each structure (A, B, and C) based on the above analysis.

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Key Concepts

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

Enantiomers

Enantiomers are a type of stereoisomer that are non-superimposable mirror images of each other. They have identical physical properties except for their interaction with polarized light and reactions in chiral environments. Understanding enantiomers is crucial for classifying molecules like d-galactose and its derivatives.
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Enantiomers vs Diastereomers Concept 1

Diastereomers

Diastereomers are stereoisomers that are not mirror images of each other. They differ in the configuration at one or more chiral centers but not all. This concept is essential for distinguishing between different stereoisomeric forms of sugars, such as d-galactose, and determining their relationships.
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Enantiomers vs Diastereomers Concept 1

Chirality

Chirality refers to the geometric property of a molecule having a non-superimposable mirror image, often due to the presence of chiral centers (typically carbon atoms bonded to four different substituents). Recognizing chirality is fundamental in stereochemistry, as it helps in identifying whether a structure is an enantiomer or a diastereomer of a reference compound like d-galactose.
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Chirality Example 1