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Friedel-Crafts Alkylation

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Reactants
t-butyl chloride + AlCl3 + benzene
t-butyl chloride + AlCl3 + benzene

Mechanism

t-butyl chloride + AlCl3 --> t-butyl cation AlCl4 -

t-butyl cation + benzene --> t-butylbenzylic cation
This product can have sevaral resonance forms.

t-butylbenzylic cation + AlCl4- --> AlCl3 + HCl + t-butylbenzene

Electron movement arrows are red; bonds and atoms that are affected are blue. The colors have no impact on the structures or mechanisms; they are just there for clarity.

Notes to Consider

Since the reaction has a carbocation intermediate, the intermediate may undergo a hydride or methyl shift to form a more stable cation. For example when using n-propylchloride (1-chrolopropane), the primary propyl cation will undergo a hydride shift to form the more stable isopropyl cation.


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