Recall that a Nucleophile is an electron pair donor (Lewis Base), and a Base is a proton acceptor (Bronsted-Lowry Base).
While the terms nucleophile and base often mean the same thing, there are some exceptions where basicity and nucleophilicity do not mirror each other.
Relative Strength Rules:
Analyze each:
Which of the following is most likely to react as a nucleophile rather a base?
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