Saponification Practice Problems
The labeled intermediate is formed during the base-catalyzed hydrolysis of the ester. Propose a suitable mechanism for the following transformations:
A Russian chemist investigated the hydrolysis of an ester by a hydroxide ion and discovered that the alkyl C—O bond remains intact while the acyl C—O bond breaks.
a. Draw the product of the hydrolysis of the following ester.
b. What would be the product if the alkyl C—O bond had broken?
Optically pure (R)-pentan-2-yl propionate was labeled with oxygen-18 at one of the oxygen atoms as shown in the structure below.
Propose a mechanism for the base-catalyzed hydrolysis of this compound showing the stereochemistry of the product. Also, show which of the product will have the oxygen-18 labeled.