Aldol reaction of cyclopentanone (Step 3)

Step 3 – Acid catalysed dehydration

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The aldol product can then undergo an acid-catalysed dehydration step via an E1 mechanism. The carbonyl group ensures that only the stable conjugated enone is formed. Firstly the alcohol groups of the aldol is protonated, and then the water acts as a leaving group to give the carbon a positive charge. A proton is then lost from the adjacent carbon to form the C=C double bond.

<Back to cyclopentanone aldol summary

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.


How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the