Why is ammonia a nucleophile?

Question

Isaac Aronson · Accepted Answer

Ammonia is a nucleophile because it has a lone pair of electrons and a δ⁻ charge on the N atom.

A nucleophile is a reactant that provides a pair of electrons to form a new covalent bond.

Sound familiar? This is the exact definition of a Lewis base. In other words, nucleophiles are Lewis bases.

A nucleophile is either a negative ion or a molecule with a δ⁻ charge somewhere.

Ammonia doesn't carry a negative charge. But it has a lone pair of electrons. And nitrogen is more electronegative than hydrogen, so the nitrogen atom has a δ⁻ charge.

So NH₃ can act as a nucleophile and attack the δ⁺ C atom of an alkyl halide.

Here's a video on ammonia as a nucleophile.

Ellie Adams · Answer

undefined Ammonia is a nucleophile because it contains a lone pair of electrons on the nitrogen atom, which it can donate to form a covalent bond with an electron-deficient atom or molecule, such as a positively charged carbon atom in an electrophilic reaction. This lone pair of electrons allows ammonia to readily form bonds with electrophiles, making it an effective nucleophile in various chemical reactions.