Electrophilic Aromatic Substitution

Bromination (Br)

Br₂ / FeBr₃

Chloration (Cl)

Cl₂ / AlCl₃

Sulfonation (SO₃H)

SO₃ / H₂SO₄

Nitration (NO₂)

HNO₃ / H₂SO₄

Friedel Crafts Alkylation (R)

R-Cl / AlCl₃

Friedel Crafts Acylation (COR)

RCO-Cl / AlCl₃

Gatterman-Koch Reaction (Formylation) (COH)

CO / HCl / AlCl₃

Formation of aromatic amine from aromatic nitro group (NH₂)

H₂ / Pd or Sn / HCl

Formation of diazonium salts from aromatic amine (N₂)

HONO / HCl

Formation of aryl chloride from a diazonium salt (Cl)

CuCl

Formation of aryl bromide from a diazonium salt (Br)

CuBr

Formation of aryl cyanide (nitrile) from a diazonium salt (CN)

CuCN

Formation of aryl iodide from a diazonium salt (I)

KI

Formation of phenol from a diazonium salt (OH)

H₂SO₄ / H₂O / Heat

Formation of aryl fluoride from a diazonium salt (F)

HBF₄ / Heat

Formation of benzene from a diazonium salt

H₃PO₂

Reduction of aromatic acyl group to create primary carbon chain (CH2CH2R)

Zn / Hg / HCl

Formation of benzene from a sulfo group

H₂O / Heat

Deactivation of Aromatic Amine (NHAc)

Ac₂O

Reactivation of aromatic amine (NH₂)