# What is an ambident nucleophile?

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Feb 6, 2018

An ambident nucleophile is an anionic nucleophile in which the negative charge is delocalized over two unlike atoms.

#### Explanation:

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, ${\text{SCN}}^{-}$, is a resonance hybrid.

Both the $\text{S}$ and the $\text{N}$ atoms can act as nucleophiles.

So, the $\text{S"_"N} 2$ reaction of an alkyl halide with "SCN"^− often leads to a mixture of an alkyl thiocyanate and an alkyl isothiocyanate.

"R-X" + "SCN"⁻ → "X"^(-) + underbrace("R-SCN")_color(red)("alkyl thiocyanate") + underbrace("R-NCS")_color(red)("alkyl isothiocyanate")

A common ambident nucleophile in organic chemistry is the enolate ion.

For example, the resonance forms of acetone enolate are

Both the $\text{C}$ and the $\text{O}$ atoms can act as nucleophiles.

Thus, the reaction of the enolate with methyl iodide gives a mixture of a ketone (1) and an enol ether (2).

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