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17.3: Nitration of Benzene (an EAS Reaction)

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    183077
  • Nitration of Benzene

    Sulfuric acid catalyzes the nitration of benzene.  It is important to note the chemical formula for the nitrate group bonded to benzene is -NO2. The chemical formula and name are assigned from an organic chemistry perspective which does not align with the inorganic perspective.

    NitrationofBenzene.jpg

    Step 1:  Nitric acid (HNO3) is protonated by sulfuric acid which causes the loss of a water molecule and formation of a nitronium ion, a strong electrophile.

    activationofnitricacid.jpg

    Steps 2 and 3:  Two pi electrons from benzene form a sigma bond with the nitronium ion to create the sigma complex. Bisulfate deprotonates the sigma complex to restore the aromatic ring as shown below.

    Mechanismofaromaticnitration.png

    Exercise

    6. Draw an energy diagram for the nitration of benzene. Draw the intermediates, starting materials, and products. Label the transition states.

     

    Answer

    6.

    solution #5.jpg

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