Question

A student intends to carry out the following synthesis: He adds sodium ethoxide to cyclohexanone (in ethanol solution) to make the enolate ion: then he adds benzyl bromide to alkylate the enolate ion, and heats the solution for half an hour to drive the reaction to completion. (a) Predict the products of this reaction sequence. (b) Suggest how this student might synthesize the correct product.

          A student intends to carry out the following synthesis:
He adds sodium ethoxide to cyclohexanone (in ethanol solution) to make the enolate ion: then he adds benzyl bromide to alkylate the enolate ion, and heats the solution for half an hour to drive the reaction to completion.
(a) Predict the products of this reaction sequence.
(b) Suggest how this student might synthesize the correct product.

Added by Jasmine N.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Alkendra Singh

12/22/2021

Step 1

This results in the formation of the enolate ion of cyclohexanone. ** Show more…

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A student intends to carry out the following synthesis: He adds sodium ethoxide to cyclohexanone (in ethanol solution) to make the enolate ion: then he adds benzyl bromide to alkylate the enolate ion, and heats the solution for half an hour to drive the reaction to completion. (a) Predict the products of this reaction sequence. (b) Suggest how this student might synthesize the correct product.