Benzyl

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure C₆H₅CH₂-. Benzyl features a benzene ring attached to a CH₂ group.

Nomenclature

In IUPAC nomenclature the prefix benzyl refers to a C₆H₅CH₂ substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl with the formula C₆H₅. The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring. For example the molecule, is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C₆H₅CH₂. The benzyl carbocation has the formula C₆H₅CH₂⁺; the carbanion has the formula C₆H₅CH₂⁻. None of these species can be formed in significant amounts under normal conditions, but they are useful referents for discussion of reaction mechanisms.

Abbreviations

The abbreviation "Bn" is frequently used to denote benzyl groups in nomenclature and structural depictions of chemical compounds. For example, benzyl alcohol can be represented as BnOH. This abbreviation is not to be confused with "Bz", which is the abbreviation for the benzoyl group C₆H₅C(O)−, or the phenyl group C₆H₅, abbreviated "Ph".