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Chapter 23: Q42E (page 783)

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

Short Answer

Expert verified

The reaction involves conjugate addition reaction followed by Claisen condensation.

Step by step solution

01

Reaction

The two steps reaction is,

02

Mechanism

The mechanism for the reaction is,

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Most popular questions from this chapter

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.

How would you prepare the following compounds from cyclohexanone?

What product would you expect from the following reaction?

What products would result after hydrolysis from the reaction of the enamineprepared from cyclopentanone and pyrrolidine with the following๐›‚-๐›ƒ-unsaturated acceptors?

(a)H2C=CHCO2Et

(b)H2C=CHCHO

(c)CH3CH=CHCOCH3

Dieckmann cyclization of diethyl 3-methylheptanedioate gives a mixture of two๐›ƒ-keto ester products. What are their structures, and why is a mixture formed?
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