Asked by Sarah

Nucleophile or electrophile?

(1) CH3COOH

(2) CH3COO-

At first, I thought that they were both Nucleophiles, but now Ive confused myself and Im not sure.. Please help!
Answered by DrBob222
Nucleophiles are Lewis bases; i.e., electron pair donors.
This link may help.
http://en.wikipedia.org/wiki/Nucleophile
So anions are nucleophiles.
Answered by Sarah
So CH3COO- is a nucleophile. It has a extra electron pair on the O- that can be donated.

But, doesnt CH3COOH also have extra valence electrons on the two O atoms that could be donated. So is it also a nucleophile, even though it does not have a negative charge?
Answered by DrBob222
It might be easier to see if you ionize the RCOOH to RCOO^- + H^+, then of course the RCOO^- is a nucleophile. But I think with the H^+ ATTACHED, it would be a weaker (much weaker?) nucleophile than when it exists as the anion alone.
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