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Alpha-Carbon Acidity = Generation of Enolates and Enols

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Matthew Donahue

In this tutorial screencast for Module 3, we examine why the alpha hydrogens to a carbonyl group are significantly more acidic than normal sp3 hybridized CH bonds. Owing to the fact that the resultant carbanion is resonance stabilized with delocalization of negative charge onto the carbonyl oxygen, this alpha position is important for the formation of new carboncarbon bonds in organic chemistry. Under basic conditions, an enolate is formed while under acidic conditions, an enol is formed. These are the two reactive intermediates that we will focus on in Module 3.

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