Mechanism of Acid-Catalyzed Enamine Formation

The overall equation for enamine formation from cyclohexanone (a ketone) and pyrrolidine (a 2°-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.

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.