In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group. Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl with the formula . The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring. For example, is referred to as a "benzylic" carbocation. The benzyl free radical has the formula . The benzyl cation or phenylcarbenium ion is the carbocation with formula ; the benzyl anion or phenylmethanide ion is the carbanion with the formula . None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of reaction mechanisms and may exist as reactive intermediates. Abbreviations The abbreviation "Bn" denotes benzyl. 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 , or the phenyl group , abbreviated "Ph". Confusingly, in old literature, "Bz" was also used for benzyl. Reactivity of benzylic centers The enhanced reactivity of benzylic positions is attributed to the low bond dissociation energy for benzylic C−H bonds. Specifically, the bond is about 10–15% weaker than other kinds of C−H bonds. The neighboring aromatic ring stabilizes benzyl radicals. The data tabulated below compare benzylic C−H bond to related C−H bond strengths. The weakness of the C−H bond reflects the stability of the benzylic radical. For related reasons, benzylic substituents exhibit enhanced reactivity, as in oxidation, free radical halogenation, or hydrogenolysis. As a practical example, in the presence of suitable catalysts, p-xylene oxidizes exclusively at the benzylic positions to give terephthalic acid: CH3C6H4CH3 + 3 O2 -> HO2CC6H4CO2H + 2 H2O Millions of tonnes of terephthalic acid are produced annually by this method. Functionalization at the benzylic position In a few cases, these benzylic transformations occur under conditions suitable for lab synthesis. The Wohl-Ziegler reaction will brominate a benzylic C–H bond: (). Any non-tertiary benzylic alkyl group will be oxidized to a carboxyl group by aqueous potassium permanganate () or concentrated nitric acid (): (). Finally, the complex of chromium trioxide and 3,5-dimethylpyrazole () will selectively oxidize a benzylic methylene group to a carbonyl: