Electrophilic Aromatic Substitution

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7 Terms

1
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why subsitution and not addition

→ Addition would destroy aromaticity (bad — lose resonance stability).

→ Substitution keeps aromaticity after the reaction.

2
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Friedel-Crafts Alkylation – Must Know Limitations

  • Only alkyl halides work (no alkenyl, alkynyl, or aryl halides).

  • Must form a stable carbocation (no unstable cations).

  • Deactivating groups (like NO₂, CF₃, or NH₂) on the benzene block the reaction.

  • Carbocation Rearrangements possible especially w/ primary alkyl halides

  • Polyalkylation happens easily (product is more reactive than starting material).
    → Fix: Use excess benzene to limit it to just one alkylation.

3
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EAS-nitration reactant and product

reactant

  • benzene ring

  • HNO3

  • H2SO4

product

  • benzene ring with the hydrogen replaced by NO2

4
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Reduction EAS-Nitration (H2 pd/c) reactant and product

reactant

  • benzene ring with NO2

  • H2

  • Pd/C

product

  • a benzene ring with the NO2 replaced with NH2

5
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EAS:Sulfination reactants and products

reactants

  • benzene ring

  • SO3

  • H2SO4

product

  • benzene ring with the NO2 replaced by a SO3H

6
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whats special about EAS:sulfonation

rxn is reversible with watre and H+

7
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