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D-glucose Isomers

2. Turn the -OH on carbon 5 around so it is close to the aldehyde carbon (carbon #1).

3. Form the hemi-acetal using the carbon #5 -OH and the carbonyl at carbon 1.
a. As you make the hemi-acetal, write out the mechanism by which this occurs. Concentrate your efforts on what is happening at C5 and C1. Review the formation of hemi-acetals in Chapter 18 of Wade.
b. Draw your product in a chair conformation with the CH2OH of carbon 6 at the top of your model.
c. Redraw your product as the Haworth (flat) projection.
d. Did you build the alpha or Beta anomer?
e. In what position (axial or equatorial) are the bulky substituents at each carbon more likely to be?
f. How many chiral carbons are there in the model now?

Solution Summary

Structure, Function and properties of D-glucose isomers.

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