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Nucleophilicity of OH(-)

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    Why is OH(-) more nucleophilic in a protic solution than a Fluoride ion? Surely it will be more affected by the Hydrogen bonding that will occur as the Oxygen will be more attracted to the protons in the protic solvent as it has a stronger negative charge? Or am I just completely wrong?
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    Fluoride is more heavily solvated than OH, so its lone pair isn't as high in energy, hence a poorer nucleophile.

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Updated: March 14, 2012
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