Electrophilic Aromatic Substitution (Ch 24)

General EAS reactant

Aromatic ring

General EAS intermediate

Arenium cation

General EAS Product

Substituted aromatic ring

EAS Halogenation reagents

X2, FeX3

EAS Halogenation reactive electrophile

X+

EAS Nitration reagents

HNO3, H2SO4

EAS Nitration reactive electrophile

NO2+

EAS Sulfonation reagents

H2SO4, SO3 (optional), heat

EAS Sulfonation reactive electrophile

SO3H+

EAS Friedel-Crafts Alkylation reagents

R-Cl, AlCl3 or R-OH, H2SO4

EAS Friedel-Craft Alkylation reactive nucleophile

Carbocation

EAS Friedel-Crafts Acylation Reagents

Acid chloride, AlCl3

EAS Friedel-Crafts Acylation reactive nucleophile

C+=O ↔ C☰O+

Clemmenson reduction reagents

arylketone or arylaldehyde + Zn(Hg) and HCl

Clemmenson reduction products

Alkane ("removes" carbonyl)

Reduction of nitro compounds reagents

Nitrobenzene + H2, catalyst or Metal, HCl

Reduction of nitro compounds product

aniline (NH2 replaces NO2)

Oxidation of alkylbenzenes to acids reagents

Alkyl benzene with at least 1 C—H bond + KMnO4 and heat

Oxidation of alkylbenzenes to acids products

carboxylic acid