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Chapter 12: Reactions of Arenes. Electrophilic Aromatic Substitution



Summary | Overview | Nitration | Sulfonation | Halogenation | Friedel-Crafts Alkylation | Friedel-Crafts Acylation | Substituent Effects | Making Polysubstituted Benzenes | Polyaromatics | Heterocycles | Self Assessment | Quiz |


Friedel-Crafts Alkylations

Chapter 12 : Reactions of Arenes. Electrophilic Aromatic Substitution

Friedel-Crafts Alkylation of Benzene

alkylation of arenes
Reaction type: Electrophilic Aromatic Substitution

Summary.

alkylation with rearrangement1,2-hydride shift during a Friedel-Crafts reaction
MECHANISM FOR THE FRIEDEL-CRAFTS ALKYLATION OF BENZENE
Step 1:
The alkyl halide reacts with the Lewis acid to form a more electrophilic C, a carbocation
Friedel-Crafts alkylation of benzene
Step 2:
The p electrons of the aromatic C=C act as a nucleophile, attacking the electrophilic C+. This step destroys the aromaticity giving the cyclohexadienyl cation intermediate.
Step 3:
Removal of the proton from the sp3 C bearing the alkyl- group reforms the C=C and the aromatic system, generating HCl and regenerating the active catalyst.

 



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