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

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FREE Expert Solution

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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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Nucleophiles and Basicity concept. You can view video lessons to learn Nucleophiles and Basicity. Or if you need more Nucleophiles and Basicity practice, you can also practice Nucleophiles and Basicity practice problems.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Zhao's class at LONESTAR.