Describe the products of the following Friedl-Crafts substitution and explain the role of the AlCl3 in the reaction: C6H6 + CH3C(O)Cl + AlCl3 = ?
C6H6 + CH3C(O)Cl = C6H5C(O)CH3 + HCl
This is an example of an electrophilic aromatic substitution reaction, with the product being a ketone. The AlCl3 serves as a catalyst, converting the acyl chloride into a stronger electrophile to encourage attack by the relatively weakly nucleophilic benzene.
AlCl3 is electron-deficient so can act as a Lewis acid and accept a pair of electrons from the acyl chloride.
CH3C(O)Cl + AlCl3 = CH3C+(O) + Al-Cl4
The CH3C+(O) now has a stronger delta + than the acyl chloride, activating it towards electrophilic substitution by the benzene.
The AlCl3 regenerated at the end of the reaction.
TH
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