Reactions of Aromatic

Compounds
By: Isman Kurniawan

Wednesday, August 6, 14

The Structure of
Benzene

The Kekule structure

The resonance representation

Wednesday, August 6, 14

The Molecular Orbitals

of Benzene
The energy diagram

Wednesday, August 6, 14

Aromatic Compounds

The criteria of aromatic compounds

1. The structure must be cyclic and planar.
2. Each atom in the ring must have an
unhybridized p orbital.
3. The unhybridized p orbitals must overlap to
form a continous ring of parallel orbitals.
4. Delocalization of the pi electrons over the
ring must lower the electronic energy.

Wednesday, August 6, 14

Huckels Rule
If the number of pi electrons in the cyclic

system is (4N+2), the system is aromatic,

where N is an integer.

Wednesday, August 6, 14

Nomenclature of
Benzene Derivatives
Self study!

Wednesday, August 6, 14

Electrophilic Aromatic
Substitution
Reaction mechanism

Wednesday, August 6, 14

Halogenation of Benzene
Reaction mechanism

Wednesday, August 6, 14

Halogenation of Benzene
Reaction mechanism

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Nitration of Benzene
Reaction
Reaction mechanism

Wednesday, August 6, 14

Nitration of Benzene
Reaction mechanism

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Sulfonation of Benzene
Reaction
Reaction mechanism

Wednesday, August 6, 14

Sulfonation of Benzene
Reaction mechanism

Wednesday, August 6, 14

The Friedel-Crafts
Alkylation
Reaction
Reaction mechanism

Wednesday, August 6, 14

The Friedel-Crafts
Alkylation
Reaction mechanism

Wednesday, August 6, 14

Exercise
Propose products for the following AlCl 3

catalyzed reactions

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The Friedel-Crafts
Acylation
Acyl group
Reaction

Wednesday, August 6, 14

The Friedel-Crafts
Acylation
Reaction mechanism

Wednesday, August 6, 14

The Friedel-Crafts
Acylation
Reaction mechanism

Wednesday, August 6, 14

The Friedel-Crafts
Acylation
The Clemmensen reduction: synthesis of
alkylbenzene

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The Effect of Substituent

Example

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The Effect of
Substituents
Directing effects of substituents

Activating groups are usually stronger directors than

deactivating groups
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Reactions of
Arenediazonium Salts
Reaction

Wednesday, August 6, 14

Reactions of
Arenediazonium Salts
Reaction

Wednesday, August 6, 14