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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鈥檚 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鈥檚 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

When cyclodecane-1,6-dione is treated with sodium carbonate, the product gives a UV spectrum similar to that of 1-acetyl-2-methylcyclopentene. Propose a structure for the product, and give a mechanism for its formation.

Show the products of the reactions of these carboxylic acids with PBr3/Br2before and after hydrolysis.

  1. pentanoic acid
  2. phenylacetic acid
  3. succinic acid
  4. oxalic acid

Predict the major products of the following reactions.

a)

Predict the products of the following reactions.

  1. cyclopentyl methyl ketone + excess CI2 + excess NaOH
  2. 1-cyclopentylethanol + excess I2 + excess NaOH
  3. propiophenone + excess Br2 + excess NaOH

(a) Although the following compound is a substituted acetone derivative, it cannot be made by the acetoacetic ester synthesis. Explain why (two reasons).

(b) The use of LDA to make enolate ions (Sections 22-2B and 22-3) has provided alternatives to the acetoacetic ester synthesis. Show how you might make the compound shown in part (a), beginning with 1,3-diphenylacetone.

(c) Enamine reactions (Section 22-4) occur under relatively mild conditions, and they often give excellent yields of compounds like the one shown in part (a). Show how you might use an enamine reaction for this synthesis, beginning with 1,3-diphenylacetone.
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