What aldehyde or ketone would be obtained when the following compound is heated in a basic aqueous solution? 5-ethyl-5-hydroxy-4-methyl-3-heptanone

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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What aldehyde or ketone would be obtained when the following compound is heated in a basic aqueous solution?

5-ethyl-5-hydroxy-4-methyl-3-heptanone

Expert Solution
Step 1

keto–enol tautomerism is a chemical equilibrium between a keto form may be a ketone or an aldehyde with an enol, a compound with a double bond, and alcohol. The keto form and enol forms are tautomers of each other. 

Step 2

 In presence of a base, it abstracts a proton from 5-ethyl-5-hydroxy-4-methyl-3-heptanone. This results in the formation of an enolate and a ketone. Ketone formed is pentan-3-one.  The resulting enolate undergoes keto-enol tautomerism to form the ketone, pentan-3-one.

Hence, 2 molecules of ketone, pentan-3-one are formed as the product.

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