Problem: Which of the following is most likely to react as a nucleophile rather a base?

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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:

  1. A negative charge will always be a stronger nucleophile than its neutral counterpart.
  2. The bulkier the base, the more basic and less nucleophilic it is.
  3. Basicity and nucleophilicity have opposite size trends in polar protic solvents. 

Analyze each:


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Problem Details

Which of the following is most likely to react as a nucleophile rather a base?

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