enolates

The Robinson Annulation

The Robinson Annulation

December 10, 2018

There’s something about intramolecular reactions that often trips students up. Conceptually, understanding an intramolecular reaction is not much different than understanding what happens when you fasten a belt,…

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An Exercise In Mind Reading?

An Exercise In Mind Reading?

April 8, 2013

The other day while going through Claisen condensations with a student, we came upon this pretty typical problem: The student duly deprotonated the alpha carbon of the ester to give the enolate, but stopped there. …

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Reagent Friday: Lithium Di-isopropyl Amide (LDA)

Reagent Friday: Lithium Di-isopropyl Amide (LDA)

August 5, 2011

In a blatant plug for the Reagent Guide, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2. Version 1.2 just got released last week, with a host of corrections and a new page in…

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Another awesome example of acid catalysis: Acids catalyze keto-enol tautomerism

Another awesome example of acid catalysis: Acids catalyze keto-enol tautomerism

May 5, 2010

Between posts on tautomerism and on lewis acid catalysis, I neglected to mention a really important point in carbonyl chemistry that illustrates another facet of acid catalysis: Acids catalyze keto-enol interconversio…

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Summary Sheet #3: Reactions of Carbonyls – The Big Picture

April 23, 2010

The reason why I harp on organic chemistry as boiling down to “nucleophile attacks electrophile” is because it’s a greatly simplifying way to look at chemical reactions. After you’ve done organ…

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Summary Sheet #2: Enols and Enolates

Summary Sheet #2: Enols and Enolates

April 14, 2010
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Keto-Enol Tautomerism: Key Points

Keto-Enol Tautomerism: Key Points

April 12, 2010

Everything you ever wanted to know (and more!) about keto-enol tautomerism.

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Carbonyls: 10 key concepts (Part 2)

Carbonyls: 10 key concepts (Part 2)

April 6, 2010

5 more key concepts: Carbonyls make adjacent alkyl groups more acidic, the more electrophilic the carbonyl, the more acidic its alpha protons, carbonyls activate alkenes toward nucleophilic attack, reactivity of alpha…

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