FriedelCrafts reaction

The FriedelCrafts reactions are a set of reactions developed by Charles Friedel

and James Crafts in 1877.

There are two main types of FriedelCrafts reactions:

alkylation reactions and acylation reactions. This reaction type is part of electrophilic
aromatic substitution. The general reaction scheme is shown below.

Friedel-Crafts Alkylation

This Lewis acid-catalyzed electrophilic aromatic substitution allows the synthesis

of alkylated products via the reaction of arenes with alkyl halides or alkenes. Since alkyl
substituents activate the arene substrate, polyalkylation may occur. A valuable, two-step
alternative is Friedel-Crafts Acylation followed by a carbonyl reduction.

Mechanism of the Friedel-Crafts Alkylation

Using alkenes :

This reaction has one big disadvantage, namely that the product is more
nucleophilic than the reactant due to the electron donating alkyl-chain. Therefore, another
hydrogen is substituted with an alkyl-chain, which leads to overalkylation of the
molecule. Also, if the chlorine is not on a tertiary carbon, carbocation rearrangement
reaction will occur. This is due to the relative stability of the tertiary carbocation over the
secondary and primary carbocations.

Steric hindrance can be exploited to limit the number of alkylations, as in the tbutylation of 1,4-dimethoxybenzene.