Experiment examines relative stereochemistry of an unknown carbohydrate, suggesting effective methods for characterization.
An experiment designed for the second semester organic chemistry course is described. An unknown carbohydrate is derivatized and recrystallized to give a single diastereomer. The absolute assignment of all hydrogen peaks can be made based on the correlation spectroscopy (COSY) spectrum, and the relative stereochemistry can be assigned based on the 3JHH coupling constants according to the Karplus relationship.
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Jonathan S. Rhoad (2011) studied this question.
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