5 Nov 2011

Organic Chemistry 3: Practice Problems (Carbohydrates)

 1.  When D-glucose is treated with sodium borohydride, optically active glucitol results.  When optically active D-galactose is reduced, however, the product is optically inactive.  Explain this loss of optical activity.

2.  Draw the expected product of the reaction of the following sugars with methyl iodide and silver oxide.
 (a) α-D-fructofuranose (b) , β -D-galactopyranose


3.  The mechanism of glycoside formation is the same as the second part of the mechanism for acetal formation.  Propose a mechanism for the formation of methyl f3 -D-glucopyranoside.


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