Orgo II Tutorial: Enol/Enolate Rxns

\({\bf{Racemization:}}\) ketones, when reacted with an acid or base, will undergo H-elimination at the alpha carbon, creating an achiral enol intermediate which can re-form a racemic mixture of ketones |dw:1542326399502:dw|
\({\bf{Enolization:}}\) two main mechanisms; one base-catalyzed, the other acid-catalyzed |dw:1542326460494:dw| |dw:1542326581489:dw|
\({\bf{Halogenation:}}\) again, two mechanisms, one acid-catalyzed, the other base-catalyzed |dw:1542326804638:dw| |dw:1542327090239:dw|
*that last product should be a C=O not a C-OH sorry* \({\bf{Haloform~Reaction:}}\) (don't confuse this w/ halogenation; halogenation of a ketone produces a ketone with a halogen on the alpha carbon; the haloform reaction creates the carboxylate salt and the haloform CHX3 |dw:1542327714893:dw|
|dw:1542327943638:dw|
Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.
Join our real-time social learning platform and learn together with your friends!