FRIEDEL-CRAFT
ALKYLATION
Contents:
• History
• Introduction
• Friedel-craft alkylation
• Mechanism of Friedel-craft alkylation
• Drawbacks of Friedel-craft alkylation
• Applications of Friedel-craft alkylation.
INTRODUCTION:-
• Introduction of alkyl group into an aromatic nucleus
in the presence of acid catalyst (usually Lewis acids)
is known as Friedel-craft alkylation
• The two primary types of Friedel-craft reactions are:
• Friedel-craft alkylation
• Friedel-craft acylation.
• Both the Friedel-craft reactions undergone by benzene is
provided below.
Friedel-craft alkylation:
• Benzene reacts with alkyl halides in the presence
of Lewis acids ( Aluminium chloride) to form alkyl
benzene.
Mechanism of Friedel-craft alkylation:
• The Friedel-craft alkylation reaction proceeds a
three- step mechanism.
• Step-1:
• Formation of electrophile.
• Step- 2:
• Attack of electrophile an aromatic ring.
• Step-3:
• Loss of proton.
Step-1:Formation of electrophile:
Draw backs of Friedel-craft alkylation:-
• It is difficult to stop the reaction when one alkyl group
has entered the ring . Di and tri alkyl benzenes are
formed.
• The alkyl group often tend to rearrange, because
Friedel-craft alkylation involves formation of carbonium
ion electrophiles .these carbonium ions can undergo
rearrangement before attacking the benzene ring.
Example :-
Limitations of Friedel-craft alkylation
reaction:-
• Some important limitations for Friedel-craft alkylation
reaction are listed below :
1)It does not react with vinyl and aryl halides.their
carbonations are far too Unstable.so avoid vinyl and aryl
halides .
Limitations of Friedel-craft alkylation
reaction:-
2)Since the carbonations formed by aryl and vinyl halides
are extremely unstable they cannot be used in this
reaction.
3)The presence of a deactivating group on the aromatic
ring(such as an NH2 group) can lead to the deactivation
of the catalyst due to formation of complexes.
Limitations of Friedel-craft alkylation
reaction:-
