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Chapter 22: Q6P (page 1156)

Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine.

Short Answer

Expert verified

Alkylation of enamine is termed the Stork reaction. This reaction alkylates or acylates a ketone’s alpha position using several alkyl or acyl halides.

Step by step solution

01

Alkylation of enamine

Alkylation of enamine is termed the Stork reaction. This reaction alkylates or acylates a ketone’s alpha position using several alkyl or acyl halides.

02

Proposing a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine

The mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine is shown below:

Mechanism for the reaction of cyclohexanone with pyrrolidine

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Most popular questions from this chapter

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.)

Show how you would accomplish the following conversions in good yields. You may use any necessary reagents.

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

Propose a mechanism for the aldol condensation of cyclohexanone. Do you expect the equilibrium to favor the reactant or the product?

Show how you would use the acetoacetic ester synthesis to make the following compounds
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