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Benzene and Aromatic Compounds. Benzene and Aromaticity. Huckel’s Rule. a ring planar each atom supplies a p orbital for electron delocalization number of delocalized electrons = 4n + 2, where n = 0, 1, 2, . 4n + 2 = 4 n = 0.5 not aromatic antiaromatic. 4n + 2 = 8

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benzene and aromatic compounds
Benzene and Aromatic Compounds

Benzene and Aromaticity

slide6

Huckel’s Rule

a ring

planar

each atom supplies a p orbital for electron delocalization

number of delocalized electrons = 4n + 2, where n = 0, 1, 2, ...

slide7

4n + 2 = 4

n = 0.5

not aromatic

antiaromatic

slide8

4n + 2 = 8

n = 1.5

nonplanar

nonaromatic

reactions of aromatic compounds
Reactions of Aromatic Compounds

Electrophilic Aromatic Substitution

reactions of aromatic compounds27
Reactions of Aromatic Compounds
  • Electrophilic Aromatic Substitution
electrophiles carbocations
Electrophiles: Carbocations

C=C + H+

ROH + H+

Friedel-Crafts alkylation: RCl + AlCl3

electrophiles acylium ions
Electrophiles: Acylium Ions

Friedel-Crafts acylation