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Aromatic Substitution

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution

These aromatic reactions are also termed electrophilic substitution reactions because an electrophile(electron deficient species) is involved in the rate determining step of the mechanism.
There are basically five such reactions given in the following table.

Name
Substituting group
Conditions
Product
Nitration
Nitro: -NO2
Heat with Conc. H2SO4 and Conc. HNO3
Nitrobenzene C6H5NO2
Sulphonation
Sulphonic acid -SO3H
Heat with Conc. H2SO4
Benzenesulphonic acid C6H5SO3H
Halogenation
Halogen -X
Heat, Cl2 , FeCl3
Chlorobenzene C6H5Cl
Alkylation
Alkyl group e.g., -CH3
Heat, CH3Cl, anhydrous AlCl3
Toluene C6H5CH3
Acylation
Acyl group -COCH3
Heat, CH3COCl, anhydrous AlCl3
Acetophenone C6H5COCH3

Alkylation and Acylation which make use of anhydrous AlCl3 a Lewis acid as a catalyst are known as Friedel-Craft reactions.

Exercise:

  1. Write chemical equations for these five reactions.
  2. What is nitration?
  3. Give a method of preparing an aromatic ketone.
  4. Write the electrophiles involved in these reactions.
  5. What is a Lewis acid?. Give two examples of Lewis acids other than AlCl3.
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