24. Enolate Chemistry: Reactions at the Alpha-Carbon

Provide the major product for the following reaction

The ketone whose ¹H NMR spectrum is shown here was obtained as the product of an acetoacetic ester synthesis. What alkyl halide was used in the synthesis?

<IMAGE>

Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:

c.

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? a. 2-pentanone

Show how the following ketones might be synthesized by using the acetoacetic ester synthesis.

Show how you would use the acetoacetic ester synthesis to make the following compounds.

Show the ketones that would result from hydrolysis and decarboxylation of the following β-keto esters.

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? c. 4-phenyl-2-butanone

Show how the following compound can be synthesized from the given starting material. (Hint: Start with an acetoacetic ester.)

Predict the products of the following reactions.

(g)

Predict the products of the following reactions.

(h)