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HomeReuschVirtual Textbook Practice ProblemsMechanism of Acid-Catalyzed Enamine Formation

The Mechanism of Enamine Formation

The overall equation for enamine formation from cyclohexanone (a ketone) and pyrrolidine (a 2º-amine) is shown here. Writing a mechanism for this reaction provides a good test of ones' understanding of acid-catalyzed processes. The question following the equation refers to the first step in the mechanism, and should be answered in order to proceed. A second question associated with an appropriate diagram will then be displayed.

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 1

When you have made a correct selection, an equation showing the reaction for that step will appear, and a new question will be posed. Incorrect selections will open an alert window displaying an explanatory message. The overall transformation will remain displayed in the colored box at each stage.


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The Mechanism of Enamine Formation


Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 2

The Mechanism of Enamine Formation


Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 3

The Mechanism of Enamine Formation

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 4

The Mechanism of Enamine Formation

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 5

The Mechanism of Enamine Formation

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 6

The Mechanism of Enamine Formation

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 7

The Mechanism of Enamine Formation

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 8

The Mechanism of Enamine Formation


Congratulations. You have finished this problem. A summary of the steps in this acid-catalyzed mechanism is shown below.

Virtual Textbook: Practice Problems — Mechanism of Acid-Catalyzed Enamine Formation, figure 9