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Chapter 23: Q66E (page 783)

The following reaction involves two successive intramolecular Michael reactions. Write both steps, and show their mechanisms.

Short Answer

Expert verified

The Intramolecular Michael reaction generally occurs in those compounds which have more than one functional group which are able to stabilize the carbonyl compounds.

In this reaction addition of nucleophile, is often referred to as donor to an acceptor.

Step by step solution

01

Formation of an enolate anion and first Michael addition

02

Second Michael addition

03

Protonation

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Most popular questions from this chapter

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

In contrast to the rapid reaction shown in Problem 23-60, ethyl acetoacetate requires a temperature over 150 ยฐC to undergo the same kind of cleavage reaction. How can you explain the difference in reactivity?

The bicyclic ketone shown below does not undergo aldol self-condensation even though it has two hydrogen atoms. Explain.

Knoevenagel condensation is a reaction involving an active methylene compound (a CH2 flanked by two electron-withdrawing groups) and an aldehyde and ketone. Propose a mechanism for the reaction below.

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.
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