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Study Objectives
By the end of this lesson students should be able to:
Describe the mechanism of electrophilic substitution in
arenes.
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Reactions of Benzene
Even though benzene is highly unsaturated it does not
acid catalyst is present however the reaction is a substitution and not an addition
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A General Mechanism for Electrophilic Aromatic Substitution In step 1 of the mechanism, the electrophile reacts with two pi electrons from the aromatic ring to form an arenium ion (stabilized by resonance)
regenerated
Halogenation of Benzene
Halogenation of benzene requires the presence of a Lewis
acid
used
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Nitration of Benzene
Nitration of benzene is a reaction that results in the
which is generated from a reaction between nitric acid and sulphuric acid.
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acid, allowing it to leave as water, forming a nitronium ion. Nitric acid is not the electrophile, it is a nitronium ion formed by protonation and dehydration of HNO3 by H2SO4. It is the nitronium ion the species that is attacked by the benzene. Loss of a proton from the sigma complex produces nitrobenzene.
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which at least one proton has been substituted by an alkyl group, e.g. Toluene:
CH3
carbon atom carrying the unpaired electron is on the side chain. Such radicals are easier to form because they are stabilized by resonance.
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Alkyl and unsaturated side chains of aromatic rings can be oxidized to the carboxylic acid using hot KMnO4
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