University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

436

Pages:

2
Author:

Niklas

C2 Epimerization: Definition: The process of converting one sugar into its C2 epimer. Epimers are stereoisomers that differ in configuration at only one chiral center. Mechanism: The mechanism involves the deprotonation of the C2 hydrogen, followed by protonation from the opposite face. This results in the inversion of configuration at the C2 carbon. Mechanism Steps: Deprotonation: The C2 hydrogen is abstracted by a base, forming a carbanion intermediate. Protonation: A proton is added to the carbanion from the opposite face, leading to the formation of the C2 epimer. Overall, the image provides a clear visual representation of the C2 epimerization reaction and its mechanism. It highlights the key steps involved in the process and the stereochemical changes that occur. Aldol-Ketose Isomerization: Overview: This reaction involves the conversion of an aldose sugar into its corresponding ketose isomer. Mechanism: The mechanism involves a base-catalyzed deprotonation of the C2 hydrogen, followed by tautomerization to form an enediol intermediate, and finally protonation at the C2 carbon to form the ketose. Mechanism Steps: Deprotonation: A base abstracts the C2 hydrogen, forming a carbanion intermediate. Tautomerization: The carbanion intermediate undergoes tautomerization, shifting the double bond and forming an enediol intermediate. Protonation: The enediol intermediate is protonated at the C2 carbon, leading to the formation of the ketose product.