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Chapter 23: Q41E (page 783)

The following reaction involves an intramolecular Michael reaction followed by an intramolecular aldol reaction. Write both steps, and show their mechanisms.

Short Answer

Expert verified

The given product is synthesised by intramolecular Michael reaction followed by Aldol reaction.

Step by step solution

01

Reaction

The given reaction is,

02

Mechanism

The mechanism for the above reaction is as follows,

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Most popular questions from this chapter

When 2-methyl cyclohexanone is converted into an enamine, only one product is formed despite the fact that the starting ketone is unsymmetrical. Build molecular models of the two possible products and explain the fact that the sole product is the one with the double bond opposite the methyl-substituted carbon.

The Mannich reaction of a ketone, an amine, and an aldehyde is one of the few three-component reactions in organic chemistry. Cyclohexanone, for example, reacts with dimethylamine and acetaldehyde to yield an amino ketone. The reaction takes place in two steps, both of which are typical carbonyl-group reactions.

(a)The first step is reaction between the aldehyde and the amine to yield an intermediate iminium ion R2C=NR2+plus water. Propose a mechanism, and show the structure of the intermediate iminium ion.

(b)The second step is reaction between the iminium ion intermediate and the ketone to yield the final product. Propose a mechanism.

Show how you would synthesize the following compound using an aldol reaction:

Which of the following compounds are aldol condensation products? What is the aldehyde or ketone precursor of each?

(a) 2-Hydroxy-2-methylpentanal (b) 5-Ethyl-4-methyl-4-hepten-3-one

The third and fourth steps in the synthesis of Hagemann’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.
See all solutions

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