Arenes and electrophilic substitution

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Explain the bonding in benzene using a delocalised $\pi$ electron model, describe its planar hexagonal structure and account for its unusual stability and tendency to undergo substitution rather than addition.
Compare the reactions of benzene with alkenes and apply this comparison to predict products and conditions for electrophilic substitution.

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Explain and apply the mechanism of electrophilic substitution in benzene, including attack by the electrophile, formation of the intermediate and loss of $\text{H}^+$ to restore aromaticity.

Describe Friedel–Crafts acylation and alkylation of benzene, including the role of halogenoalkanes or acyl chlorides and $\text{AlCl}_3$/$\text{FeCl}_3$-type catalysts, and predict the products formed.

Interpret the directing and activating effects of substituents already attached to the benzene ring, including phenol, phenylamine, halogens and alkyl groups, and apply oxidation of alkylbenzene side chains to carboxylic acids in synthetic contexts.

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