Electrophilic Aromatic Substitution

electrophilic aromatic substitution

A reaction in which an electrophile is substituted for a hydrogen on an aromatic ring.

Five EAS reactions

Halogenation

Friedel-Crafts Alkylation

Friedel-Crafts Acylation

Nitration

Sulfonation

Mechanism for Friedel-Crafts Alkylation

Mechanism of electrophilic aromatic substitution of a halide

Reagents for electrophilic substitution halide to aromatic ring?

X2, FeX3

Mechanism for the nitration of benzene

Reagents for nitration of benzene

Reagents for sulfonation of benzene

fuming sulfuric acid

Mechanism for the sulfonation of benzene

Friedel-Crafts Acylation

RCOCl, AlCl3

What structural feature does an O/P director have?

Donate electrons to aromatic ring

What is an ortho/para director?

Substituents on benzene rings that hat set the location of the next groups onto the ortho and para positions of a ring

Which groups are O/P directors?

Ortho/para directors (activate/deactivate) the ring?

activate

mechanism for ortho/para directors

Meta directors

Substituents on benzene rings that set the location of the next groups onto the meta positions of a ring

What structural feature do meta directors have?

electron withdrawing groups

Types of meta directors

Meta directors (activate/deactivate) the ring?

deactivate

Mechanism for meta directors