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12 MECHANISMS

Aromatic Substitutions

Benzene Bromination

Benzene Bromination

Electrophilic aromatic bromination of benzene.

Benzene Sulfonation

Benzene Sulfonation

A reversible SO3 substitution onto the ring.

Benzene Nitration

Benzene Nitration

The nitronium ion substitutes onto benzene.

Friedel–Crafts Alkylation

Friedel–Crafts Alkylation

A carbocation alkylates the aromatic ring.

Friedel–Crafts Acylation

Friedel–Crafts Acylation

An acylium ion installs a ketone group.

Phenol Bromination

Phenol Bromination

The activated ring brominates readily.

Phenol Acetate Bromination

Phenol Acetate Bromination

A protected phenol directs the bromination.

Benzoic Acid Nitration

Benzoic Acid Nitration

The meta-directing carboxyl controls the site.

Chlorobenzene Nitration

Chlorobenzene Nitration

Chlorine directs the electrophile ortho and para.

Nucleophilic Aromatic Substitution

Nucleophilic Aromatic Substitution

Addition–elimination through a Meisenheimer complex.

Benzyne Formation

Benzyne Formation

Strong base eliminates to a strained benzyne.

Benzyne Diels–Alder

Benzyne Diels–Alder

Benzyne is trapped by a diene in a cycloaddition.