What Makes a Good Enolate

Electrostatic potential map for 2-butanore enolate shows most negatively-charged regions (in red) and less negatively-charged regions (in blue). 

Deprotonation at carbon adjacent to a carbonyl group leads to an enolate anion, e.g., deprotonation of acetone. 

Examine the geometry and electrostatic potential map for acetone enolate. Are the CC and CO bonds in the enolate more similar to those in acetone or propen-2-ol precursors Is the negative charge primarily located on oxygen or on carbon Assuming this enolate is a hybrid of the two resonance contributors as shown above, which, if either, appears to be the major contributor  

Compare electrostatic potential maps of enolates derived from 2-butanone, 4,4-dimethyl-2-pentanone, 4,4,4-trifluoro-2-butanone and l-phenyl-2-propanone with those of acetone. Which substituents cause significant changes in the electronic structure of these enolates and what are the nature of these changes Justify your answers by making drawings of any important resonance contributors. 

Is the most delocalized enolate also the most easily formed enolate Calculate relative deprotonation energies from the enolate precursors using the deprotonation energy of acetone as a standard. 

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