Friedel-Crafts Acylation [PDF]

The Acylium Ion is the Electrophile in. Friedel-Crafts Acylation Reactions. The active electrophile for. Friedel-Crafts
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Idea Transcript

Friedel-Crafts Acylation O

An acyl group has the structure R

An alkyl group has the structure

+

O R Cl acyl chloride

H

O

+ H

O

R O R acid anhydride

R

1) AlCl3 2) H2O 1) AlCl3 2) H2O

http://www.chemtube3d.com/

R

O

The Acylium Ion is the Electrophile in Friedel-Crafts Acylation Reactions The active electrophile for Friedel-Crafts Acylation is the acylium ion

R C O AlCl4

How does it form? R C O acylium ion

Cl

O R C Cl

+

Cl

Al

For the acylium ion, which resonance contributor is more important? Why?

[AN] (or [AdN]) [DN] (or [Eβ])

[AN]

O

ion pair dissociation / formation

Cl

R C Cl Al Cl

Cl

Cl

All atoms have octet of electrons

Friedel-Crafts Alkylation H

+

R Cl

AlCl3

R

+

HCl

The active electrophilic species is the carbocation R+

Example: H

+

Cl isobutyl chloride

+ tert-butylbenzene

HCl

Mechanism of Friedel-Crafts Alkylation CH3

Cl

+

CH3 CH CH2–Cl

Cl

Al

CH3 Cl

[AN]

Cl

CH3 C

CH2–Cl Al

H

Cl

Cl

isobutyl chloride aluminum chloride complex

H

[1,2R] + [DN]

H CH3

[AE]

CH3

C

CH3

http://www.chemtube3d.com/

AlCl4

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