24. Enolate Chemistry: Reactions at the Alpha-Carbon

Acetoacetic Ester Synthesis

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Acetoacetic Ester Synthesis

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Multiple Choice

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?

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Textbook Question

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

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Textbook Question

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

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Textbook Question

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

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Textbook Question

Show how the following ketones might be synthesized by using the acetoacetic ester synthesis. (a) (b) (c)

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Textbook Question

Show how you would use the acetoacetic ester synthesis to make the following compounds. (a) (b) (c)

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Textbook Question

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

(a) <IMAGE>

(b) <IMAGE>

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Textbook Question

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl

ketones?

c. 4-phenyl-2-butanone

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Textbook Question

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

<IMAGE>

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Textbook Question

Predict the products of the following reactions.

(g) <IMAGE>

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Textbook Question

Predict the products of the following reactions.

(h) <IMAGE>

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