Organic Chemistry Help: Retrosynthesis on an enolate

Hi everybody, one of the questions I hear alot is about enolate product.  How do you do the retrosynthetic analysis on one?  How do you even know it came from an enolate reaction?  Here is an example to look at:

As you can see here, a possible enolate product is an α,β-unsaturated ketone.  When you see one of these types of ketones, disconnect first at the double bond and “insert” an oxygen atom, as shown above.  Now, it becomes more evident which two carbonyls were participants in the original reaction.
Remember that in most cases, an α,β-unsaturated ketone can be derived from an enolate reaction.
Hopefully this was somewhat helpful.  For more information on this and other topics, please visit organic chemistry.
Good luck and happy reacting.

Dr. Michael Pa got a bachelors degree in chemistry from Binghamton University, a masters degree in organic chemistry from the University of Arizona and a Ph.D. in organic chemistry from the University of Arizona. His research focus was on novel pain killers which were more potent than morphine but designed to have fewer side effects. There may even be a patent or two that came out of it. Prior to all of this, he was a chemist at Procter and Gamble. After all of that, he (briefly) worked as a post-doctoral assistant at Syracuse University, working on novel organic light-emitting diodes (OLEDs). In between, he did NOT compete at the 1996 Olympics, make the Atlanta Braves opening day roster, or become the head coach of the Indiana Pacers, as he had intended. #fail During this entire time, he always loved helping students, especially if they were struggling with organic chemistry. In 2006, Dr. Pa founded in order to make learning organic chemistry fast and easy. 14 years and about 60,000 students later we are still helping students to learn organic chemistry one reaction at a time at

3 thoughts on “Organic Chemistry Help: Retrosynthesis on an enolate”

  1. This is a reverse aldol condensation, correct? I say this because that type of nucleophilic enolate reaction is followed by condensation which then forms the TM conjugated α,β-unsaturated ketone.

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