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Which item is not nucleophilic? a proton a carbanion an imidazole?

User Rishal
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The term "nucleophilic" describes substances that have excess electron pairs that they want to donate or share.

A proton does not have any excess electron pairs, so it is not nucleophilic.
A carbanion has a pair of excess electrons on a carbon atom, so it is nucleophilic.
An imidazole has excess electrons on its nitrogen atom, so it is nucleophilic.

Therefore, only the proton is not nucleophilic.
User Sabo Boz
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