Question
Question: What is the difference between a base and a nucleophile?...
What is the difference between a base and a nucleophile?
Solution
A nucleophile is an element or molecule that seeks a positive centre in a chemical reaction, just as the nucleus in an atom since the nucleophile has an electron pair that is accessible for bonding.
A base is a compound that reacts with hydrogen ions to neutralise an acid. The majority of bases are minerals that combine with acids to produce water and salts.
Complete answer:
A nucleophile is an electron-rich species that donates two electrons to carbon and forms a bond with it. A Base is also an electron-rich species, but it gives hydrogen a pair of electrons.
Most nucleophiles are Lewis bases and vice versa, the two are connected. Some strong bases are also good nucleophiles, while some good nucleophiles are weak bases. A species can be both a weak nucleophile and a strong base.
While Nucleophiles and bases are similar and have a similar property, they also have differences.
The differences between a base and nucleophile are:
Base | Nucleophile |
---|---|
They attack acidic protons. | They attack electron-deficient carbons. |
They have a lower electronegative charge, are greater in size, and are easier to oxidise. | They have a lower electronegative charge, are greater in size, and are easier to oxidise. |
Bases are affected by temperature. | Nucleophiles are affected by speed or electricity. |
Bases are involved in the forming of strong bonds. | Nucleophiles are involved in the reaction speed. |
Basicity reactions involve bases. | Electrophilicity reactions involve nucleophiles. |
Bases are slow chemical mediators that retain an acid-based equilibrium during reversible conditions. | Nucleophiles are quick and immediate chemical mediators required during irreversible conditions. |
Note: Nucleophilicity and basicity typically go hand in hand. However, these two words are not interchangeable. There are times where a species is a good nucleophile but a bad base, or vice versa.