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Not really sure what the principle would be. Maybe it has something to do with the resonance capability of the two Os in CH3CO2

Joshua Morris
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  • "Not really sure what the principle would be. Maybe it has something to do with the resonance capability of the two Os in CH3CO2". What is the consequence for the negative charge in acetate vs ethanolate? – imalipusram May 01 '20 at 01:11

1 Answers1

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Since a nucleophile is a species that is donating a pair of electrons, it’s reasonable to expect that its ability to donate electrons will increase as it becomes more electron rich. As electron density increases, nucleophilicity increases.

In our first option(CH3CO2-), resonance is occurring between the two oxygen atoms, decreasing the electron density on oxygen atom.

Nothing like this occurs in our second option(CH3CH2O-) which means it has more electron density than the first compound, hence second compound is more nucleophilic.

R_Squared
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