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Chapter 23: Q9P (page 764)

Treatment of a 1,3-diketone such as 2,4-pentanedione with base does not give an aldol condensation product. Explain.

Short Answer

Expert verified

Due to the formation of the stable compound at equilibrium, treatment of a 1,3-diketone such as 2,4-pentanedione with base does not give an aldol condensation product.

Step by step solution

01

Formation of enolate ions:


02

Results of treatment

Due to the formation of stable enolate ion as seen in [A] enolate ion at equilibrium, it becomes unreactive

Hence,1,3-diketone on treatment with base does not give an aldol condensation while in the case of [B] enolate ion it is unstable and forms a negligible amount of product.

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Most popular questions from this chapter

Based on your answers to Problem 23-27, predict the dehydration product for each reaction and provide the mechanism.

1-Butanol is prepared commercially by a route that begins with an aldol reaction. Show the steps that are likely to be involved.

What ketones or aldehydes might the following enones have been prepared from by aldol reaction?

The following reaction involves a conjugate addition reaction followed by an intramolecular Claisen condensation. Write both steps, and show their mechanisms.

The Stork enamine reaction and the intramolecular aldol reaction can be carried out in sequence to allow the synthesis of cyclohexanones. For example, the reaction of the pyrrolidine enamine of cyclohexanone with 3-buten-2-one, followed by enamine hydrolysis and base treatment, yields the product indicated. Write each step, and show the mechanism of each.
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