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ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > Hydrocarbons > Aromatics > Properties of Aromatics > Aromaticity > Aromaticity

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Aromaticity

Table of Contents

The adjective "aromatic" is used by organic chemists in a rather different way than it is normally applied. It has its origin in the observation that certain natural substances, such as cinnamon bark, wintergreen leaves, vanilla beans and anise seeds, contained fragrant compounds having common but unexpected properties. Cinnamon bark, for example, yielded a pleasant smelling compound, formula C9H8O, named cinnamaldehyde.

Because of the low hydrogen to carbon ratio in this and other aromatic compounds (note that the H:C ratio in an alkane is >2), chemists expected their structural formulas would contain a large number of double or triple bonds. Since double bonds are easily cleaved by oxidative reagents such as potassium permanganate or ozone, and rapidly add bromine and chlorine, these reactions were applied to these aromatic compounds. Surprisingly, products that appeared to retain many of the double bonds were obtained, and these compounds exhibited a high degree of chemical stability compared with known alkenes and cycloalkenes (aliphatic compounds). On treatment with hot permanganate solution, cinnamaldehyde gave a stable, crystalline C7H6O2 compound, now called benzoic acid. The H:C ratio in benzoic acid is <1, again suggesting the presence of several double bonds. Benzoic acid was eventually converted to the stable hydrocarbon benzene, C6H6, which also proved unreactive to common double bond transformations, as shown below. For comparison, reactions of cyclohexene, a typical alkene, with these reagents are also shown (green box). As experimental evidence for a wide assortment of compounds was acquired, those incorporating this exceptionally stable six-carbon core came to be called "aromatic".

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