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Aromatic Hydrocarbons Structure of Benzene - simplest aromatic hydrocarbon is benzene C6H6 - sweetish-smelling liquid first isolated in 1825 by Michael Faraday from the oily residue that had collected in gas lines - this formula has so few hydrogen atoms for the number of carbon atoms that an unsaturated molecule would seem likely - Kekule proposed a ring structure involving alternating single and double bonds years later Dewar and Ladenburg proposed very different molecules for the benzene molecule - benzene is a planar molecule - benzene should behave as if it was an alkane if so it should react with bromine to give an addition product and with potassium permanganate to give an oxidation product - in fact when bromine and benzene react together a substitution product is formed - benzene and potassium permanganate do not react at all - from enthalpy measurements we find that benzene is about 150kJ mol-1 more stable than a compound having the Kekule structure should be Reactions of Benzene - substitution reactions dominate the chemistry of benzene - eg the reaction between bromine and benzene in the presence of an iron catalyst to produce bromobenzene - despite its preference for substitutions under extreme conditions benzene can be made to undergo addition reactions - eg at pressures of 20 to 30 MPa benzene can be hydrogenated to cyclohexane Other Common Aromatic Compounds - next simplest aromatic hydrocarbon is toluene methylbenzene is almost as good as a solvent as benzene and is comparatively less harmful - it is possible to have compounds containing connected benzene rings - Naphthalene a compound in which two benzene rings share a common side is used as a moth repellent - The carcinogenic compound 34-benzopyrene is produced in significant quantities in any burning or charring process thus both cigarette smoke and char broiled foods contain this hazardous chemical ------------------------------------------------------------------------ Bibliography no bibliography
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