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Aromatic Substitution reactions: (a) Electrophilic substitution (b) Nucleophilic Substitution reactions Electrophilic Aromatic Substitution Electrophilic addition reaction of an alkene General Mechanism for Electrophilic Aromatic Substitution Reactions The following are the five most common electrophilic aromatic substitution reactions: No deuterium/hydrogen isotope effect in most cases. If the hydrogen departed • Before the electrophile added • Or if the arrival of the electrophile and the departure of the proton were simultaneous Then we would expect an isotope effect on the rate of reaction if we replace H by its more massive isotope D The lack of an isotope effect means that the proton is lost after the rds. Isolation of Arenium Ion Intermediates: Even the simplest arenium ion from benzene has been detected by NMR at low temperatures (-134 oC). Halogenation of Benzene Comparison with Alkenes • Moister in the air inactivate the catalyst The order of reactivity of halogen is F2 > Cl2 > Br2 > I2 Controlled fluorination is difficult. Nitration of Benzene Sulfonation of Benzene Effect of Substitution ➢ Nitration of Toluene is 25 times faster than benzene. ➢ Nitrobenzene is much less reactive than benzene. • Activating groups • Deactivating groups • Inductive effect • Resonance effect Effect of substituent on orientation Alkyl group • Inductive stabilization • Activating group • Ortho/ para dir ...
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