Friedel-Crafts

Electrophilic aromatic substitution

Friedel-Crafts refers to a class of chemical reactions that attach carbon groups to aromatic rings using a catalyst, typically aluminum chloride.

Named for chemists Charles Friedel and James Crafts, these reactions come in two forms: alkylation (adding alkyl groups) and acylation (adding acyl groups).

Friedel-Crafts alkylation is a standard method for synthesizing substituted benzenes.

alkylation

benzene

Aromatic hydrocarbon solvent

substrate · electrophile · catalyst

acylation

ketone

Carbonyl between two carbons

acyl group · synthesis · reversibility

mechanism

pi electrons

Delocalized bonding electrons above/below plane

  • attackAggressive act against another
industrial

polystyrene

Lightweight synthetic foam plastic

petrochemical · plastics · manufacturing · scale-up

Categories
Opposites
reaction mechanism type

Friedel-CraftsSN2 reaction

Second-order nucleophilic displacement

oxidative addition · Negishi coupling · SN2 · SN1 · Diels-Alder reaction

Family

Crafts, craft, crafts, crafted, crafting, craftsman, craftsmanship, craftsmen, crafty

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Used worldwide · Timeless · Abstract · Rated G