Electrophilic Aromatic Substitution

Halogenation

rings react w/ Br or Cl in presence of Lewis Acid: FeCl3, FeBr3, AlBr3, or AlCl3

Friedel-Crafts Alkylation

R-X (Cl, Br, etc.), adds R group and removes the X. Occurs w/ AlCl3

Friedel-Crafts Acylation

RCO-X (Cl, Br, etc.), adds RC=O group and removes X. Occurs w/ AlCl3

Nitration

the substitution of a nitro group (-NO2) for a hydrogen on an aromatic ring. Occurs w/ HNO3 in H2SO4

Sulfonation of Benzene

the substitution of a SO3 for a hydrogen, occurs in "fuming" H2SO4. *Reversible w/ dilute H2SO4

Polysubstituted Benzenes two ortho/para

the more activating substituent wins for directing (EDG).

Polysubstituted Benzenes ortho/para with meta

the ortho/para directing group wins

Two meta-directing groups

the new substituent locates at the position meta to the stronger deactivating group

Aniline w/ lewis acid present

no reaction

Aniline w/ strong acid like H2SO4

meta directing product w/ protonated amine

Aniline and phenol in the absence of an acid

highly active in EAS