Embedded Files
Introduction
Introduction
This page focuses on reactions that deal with the alpha carbon in carbonyl-containing compounds.
Reactions
Reactions
Acid-catalyzed ketone-enol tautomerization
Acid-catalyzed ketone-enol tautomerization
Tautomerization reactions are part of other mechanisms and are shown here and not in other places for simplicity
Base-catalyzed ketone-enol tautomerization
Base-catalyzed ketone-enol tautomerization
α halogenation
α halogenation
These reactions works with chlorine, bromine, and iodine.
In acidic conditions
In acidic conditions
In basic conditions
In basic conditions
Haloform reaction (also in basic conditions)
Haloform reaction (also in basic conditions)
When performed with iodine, this reaction may be used as a test for a methyl ketone
Hell-Volhard-Zelinsky reaction
Hell-Volhard-Zelinsky reaction
Aldol
Aldol
If the reaction is performed with heat, elimination in an E1cb reaction can occur. If extensive conjugation results from E1cb, heat may not be needed.
Elimination under basic conditions
Elimination under basic conditions
Elimination under acidic conditions
Elimination under acidic conditions
Claisen condensation
Claisen condensation
Intramolecular Claisen condensation (Dieckmann cyclization)
Intramolecular Claisen condensation (Dieckmann cyclization)
Alkylation of the α proton
Alkylation of the α proton
Use LDA at -78˚C to alkylate the less substituted side. Use a nonsterically hindered base like NaH to alkylate the more substituted side
Malonic ester synthesis
Malonic ester synthesis
Acetoacetic ester synthesis
Acetoacetic ester synthesis
Michael addition
Michael addition
Stork enamine synthesis
Stork enamine synthesis
Click here for the mechanism of enamine formation.
Google Sites
Report abuse