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Why Is the Carbon Atom Typically the Nucleophilic Site of an Enolate

Question 6

Multiple Choice

Why is the carbon atom typically the nucleophilic site of an enolate anion? Why is the carbon atom typically the nucleophilic site of an enolate anion?   A) Most of the negative charge resides on the carbon atom. B) The resonance form with the negative charge on carbon is the major contributor. C) The alkoxy anion will not act as a Lewis base, due to oxygen electronegativity. D) The HOMO of the enolate has its largest lobe at the beta-carbon. E) The bonding MO of the enolate has its highest electron density around the oxygen.


A) Most of the negative charge resides on the carbon atom.
B) The resonance form with the negative charge on carbon is the major contributor.
C) The alkoxy anion will not act as a Lewis base, due to oxygen electronegativity.
D) The HOMO of the enolate has its largest lobe at the beta-carbon.
E) The bonding MO of the enolate has its highest electron density around the oxygen.

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