Ketyl

Before: Toluene is refluxed with sodium-benzophenone to dry and deoxygenate it.
After: The deep blue coloration of the benzophenone ketyl radical shows that the toluene to be distilled is dry and oxygen-free.

A ketyl group in organic chemistry is an anion radical that contains a group R2C−O•. It is the product of the 1-electron reduction of a ketone.

Another mesomeric structure has the radical position on carbon and the negative charge on oxygen.[1]

A ketyl

Ketyls can be formed as radical anions by one-electron reduction of carbonyls with alkali metals. Sodium and potassium metal reduce benzophenone in THF solution to the soluble ketyl radical. Ketyls are also invoked as intermediates in the pinacol coupling reaction.

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "ketyls". doi:10.1351/goldbook.K03389