Aldol reaction of cyclopentanone

Below are shown the mechanistic steps involved in the Aldol reaction of a symmetrical cyclic ketone. The final enone is formed in a good yield both in acid or base conditions. Here the acid-catalysed reaction is used to illustrate the mechanism. ‘Click’ the different stages to view 3D models of the reaction:

  • Step 1 – Acid catalysed enolization

  • Step 2 – Acid catalysed aldol addition

  • Step 3 – Acid catalysed dehydration

D. S. Noyce and W. A. Pryor, J. Am. Chem. Soc., 1955, 77, 1397–1401.

C. L. Perrin and K.-L. Chang, J. Org. Chem., 2016, 81, 5631–5635.

 

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