Reactions of Aromatic Compounds - PowerPoint PPT Presentation

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Reactions of Aromatic Compounds

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  1. Reactions of Aromatic Compounds

  2. => Electrophilic Aromatic Substitution Electrophile substitutes for a hydrogen on the benzene ring.

  3. Mechanism =>

  4. Bromination of Benzene Requires a stronger electrophile than Br2. Use a strong Lewis acid catalyst, FeBr3. Animation Animation Animation =>

  5. Energy Diagramfor Bromination =>

  6. => Chlorination and Iodination Chlorination is similar to bromination. Use AlCl3 as the Lewis acid catalyst. Iodination requires an acidic oxidizing agent, like nitric acid, which oxidizes the iodine to an iodonium ion.

  7. Nitration of Benzene Use sulfuric acid with nitric acid to form the nitronium ion electrophile. NO2+ then forms a sigma complex with benzene, loses H+ to form nitrobenzene. =>

  8. => Sulfonation Sulfur trioxide, SO3, in fuming sulfuric acid is the electrophile.

  9. => Benzene-d6 Desulfonation All steps are reversible, so sulfonic acid group can be removed by heating in dilute sulfuric acid. This process is used to place deuterium in place of hydrogen on benzene ring.

  10. => Nitration of Toluene Toluene reacts 25 times faster than benzene. The methyl group is an activator. The product mix contains mostly ortho and para substituted molecules.