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Chapter 23: Q44E (page 783)

Propose a mechanism for the following base-catalyzed isomerization:

Short Answer

Expert verified

The product is formed by the base-catalyzed isomerization.

Step by step solution

01

Reaction

The given reaction is,

02

Mechanism

The mechanism for the above reaction is,

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Most popular questions from this chapter

The first step in the citric acid cycle of food metabolism is reaction of oxaloacetate with acetyl CoA to give citrate. Propose a mechanism, using acid or base catalysis as needed.

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

The compound known as Hagemannโ€™s ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation.

(a)The first step is an aldol-like condensation between ethyl acetoacetate and formaldehyde to yield an ฮฑ,ฮฒ-unsaturated product. Write the reaction, and show the structure of the product.

(b)The second step is a Michael reaction between ethyl acetoacetate and the unsaturated product of the first step. Show the structure of the product.

The third and fourth steps in the synthesis of Hagemannโ€™s ester from ethyl acetoacetate and formaldehyde (Problem 23-71) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.

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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