Epimerization quiz Flashcards
Epimerization quiz
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At which carbon position does epimerization typically occur in monosaccharides?
Epimerization typically occurs at the C2 position in monosaccharides. What is the main reason bases are generally avoided with monosaccharides?
Bases are avoided because they can lead to complex mixtures due to multiple isomerizations. What is the result of epimerization at the C2 position of beta-D-glucopyranose?
Epimerization at the C2 position of beta-D-glucopyranose can convert it into D-mannopyranose. What is the role of the enolate mechanism in epimerization?
The enolate mechanism involves deprotonation of the alpha carbon, forming an enolate that can lose stereochemical information at C2. How does the enediol mechanism differ from the enolate mechanism?
The enediol mechanism forms an enediol intermediate with two hydroxyl groups, leading to possible inversion at C2. What happens to the stereochemistry of the hydroxyl group during epimerization?
The stereochemistry of the hydroxyl group at C2 can racemize, allowing it to switch positions. Why is the C2 position of a monosaccharide susceptible to epimerization in base?
The C2 position is susceptible due to the acidity of the alpha carbon, which is more easily deprotonated. What is the significance of the enediol intermediate in the epimerization process?
The enediol intermediate allows for the loss of stereochemical information, enabling the hydroxyl group to switch positions. What is the outcome of the enolate mechanism in terms of stereochemistry?
The enolate mechanism results in the loss of stereochemical information at C2, allowing for racemization. What is the final result of both the enolate and enediol mechanisms in epimerization?
Both mechanisms result in the formation of an epimer with the hydroxyl group at C2 in a different stereochemical position.
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