What is an ambident nucleophile?
An ambident nucleophile is an anionic nucleophile in which the negative charge is delocalized over two unlike atoms.
A nucleophile is a chemical species that can donate an electron pair and form a bond to a carbon atom. For example,
The word ambident comes from two Latin words: ambi = "on both sides" + dens = "tooth".
So an ambident nucleophile has "teeth" on two sides.
It can attack from two different places and form two different products.
For example, the thiocyanate ion,
A common ambident nucleophile in organic chemistry is the enolate ion.
For example, the resonance forms of acetone enolate are
Thus, the reaction of the enolate with methyl iodide gives a mixture of a ketone (1) and an enol ether (2).