Mekanisme

Friedel-
Crafts

Rifkarosita Putri Ginaris., M.Farm

Electrophilic alkylations : Friedel- Crafts
reactions

Particularly useful reactions result from Friedel- Crafts

alkylations and acylations, in which the electrophile is developed
from either an alkyl halide or an acyl halide in the presence of a
Lewis acid
A. Alkylation

The alkylation
reaction is
mechanistically
similar to the
halogenation process
above, with the Lewis
acid increasing
polarization in the
alkyl halide
 The Friedel-Crafts alkylation Limitation

1. Only alkyl halides can be used. Aromatic (aryl) halides and vinylic halides
do not react, because aryl and vinylic carbocations are too high in energy
to form under Friedel – Craf ts conditions.
2. Don’ t succeed on aromatic rings that are substituted either by
a strongly electron-withdrawing group such as carbonyl (C=O) or
by an amino group (-NH2, NHR, -NR2).
3. Of ten diffi cult to stop the reaction af ter a single substitution.
Once the fi rst alkyl group is on the ring, a second substitution
reaction is facilitated for reasons we’ll discuss in the next
section. Thus, we often observe potyaikylation.
4. A skeletal rearrangement of the alkyl carbocation electrophile sometimes
occurs during reaction, particularly when a primary alkyl halide is used.
B. Acylation

Aromatic ring is acylated by reaction with a carboxylic acid

chloride, RCOCl, in the presence of AlCl 3
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