Study sets, textbooks, questions
Upgrade to remove ads
Alpha substitution reactions of carbonyls
Terms in this set (14)
Enolates and enols
Enolates are better nucleophiles because they have a negative charge
How to deprotonate alpha-hydrogen
More substituted alpha-hydrogen gets deprotonated with typical base (-OH)
Less substituted alpha-hydrogen gets deprotonated with LDA
Base-promoted alpha halogenation
all alpha hydrogens are replaced with halogen
Acid-catalyzed alpha halogenation
only one alpha hydrogen replaced with halogen
all alpha hydrogens replaced with D atom regardless of acid or basic
need a CH3
- produces a yellow precipitate if methyl ketone is present - useful lab test
A reaction in which an aldehyde or ketone acts as both the electrophile and nucleophile, resulting in the formation of a carbon-carbon bond in a new molecule called an aldol.
Just like alcohol condensation, except with esters
- enolate adds to an ester
With B-Keto esters if you add heat it decarboxylates the ester group.
This occurs and detaches making a double bond but is replaced with an H during acid quench
Acetoacetic Ester Synthesis
*the production of a ketone from acetoacetic ester due to the strongly acidic properties of the alpha hydrogen.
*a base is added to remove the alpha hydrogens.
*the resulting enolate ion is alkylated by an alkyl halide or tosylate leaving the alkyloacetoacetic ester.
*the acetoacetic ester synthesis is finished with the decarboxylation leaving the ketone.
Malonic Ester Synthesis
The process by which to convert a malonic ester to a carboxylic acid
Sets found in the same folder
Summary of OC Lab Tests
Other sets by this creator