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Friedel Craft's Alkylation&Acylation

1) Friedel-Crafts alkylation and acylation involve the formation of carbocation or acylium ion intermediates using Lewis acids like AlCl3 or FeBr3 to alkylate or acylate aromatic rings. 2) Problems with Friedel-Crafts alkylation include only working for activated aromatics, further alkylation occurring due to increased reactivity, and carbocation rearrangement. 3) Reducing carbonyl groups from acylation products to alkyl groups via Clemmensen or Wolff-Kishner reductions allows alkylation of aromatics not possible with direct alkylation.

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212 views4 pages

Friedel Craft's Alkylation&Acylation

1) Friedel-Crafts alkylation and acylation involve the formation of carbocation or acylium ion intermediates using Lewis acids like AlCl3 or FeBr3 to alkylate or acylate aromatic rings. 2) Problems with Friedel-Crafts alkylation include only working for activated aromatics, further alkylation occurring due to increased reactivity, and carbocation rearrangement. 3) Reducing carbonyl groups from acylation products to alkyl groups via Clemmensen or Wolff-Kishner reductions allows alkylation of aromatics not possible with direct alkylation.

Uploaded by

Jafin
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Friedel-Crafts Alkylation

General scheme:

or

(R = alkyl)
AlCl3 or
FeBr3

Friedel-Crafts Alkylation
Depends on formation of alkyl cation (or incipient cation) intermediate:

2 or 3 halide:

1 or CH3 halide:

These intermediates react identically in the Friedel-Crafts


alkylation reaction.

Problems with Friedel-Crafts Alkylation


1. Only succeeds for benzene, activated aromatics.
2. Alkylation makes aromatic ring more reactive to
further alkylation.
CH3Br
FeBr3

CH3Br
FeBr3
+

2nd reaction is faster than the 1st (because


aromatic ring is activated);
Cant stop reaction at monoalkylated product.

further
alkylation

(Can address by using excess starting material.)

Problems with Friedel-Crafts Alkylation


3. Intermediate cation can rearrange (leading to
unexpected products).

NOT
FeBr3

due to
rearrangement
of

Friedel-Crafts Acylation
General scheme:

1.

, AlCl3
+

2. H2O

Depends on formation of acylium ion intermediate:

+
acylium
ion

Reducing Carbonyls to Alkyl Carbons


Clemmensen Reduction

Zn(Hg),
HCl/H2O

(acidic
conditions)

Wolff-Kishner Reduction

1. N2H4
2. KOH,

(basic
conditions)

Both useful for converting Friedel-Crafts acylation products to alkylated


aromatic molecules that cant be made by Friedel-Crafts alkylation.

Characteristics of Combined Friedel-Crafts


Acylation/Clemmensen Reduction
1. Still only succeeds for benzene, activated
aromatics.
2. Acylation makes aromatic ring less reactive to
further acylation.
Electron-withdrawing C=O
deactivates product.

3. Acylium ion is resonance-stabilized, doesnt


rearrange.

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