Benzene and Phenol

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  • Benzene and Phenols
    • Benzene
      • Kekule
        • Ring Structure
          • 3 C=C and     3 C-C
          • 2 Forms, in equilibria, changing before reaction can occur.
        • Problems
          • C-C Bond Lengths
            • All C-C same length
            • X-Ray Diffraction
            • 0.139nm
          • Benzene Hydrogenation
            • Benzene more stable
            • Cyclohexa-1,3,5-triene: -360kJmol-1
      • Delocalised Model of Benzene
        • Bond angles around each Carbon: 120 (trigonal planar)
        • 4 outer e- (2 bound to C 1 to H) 1 left in 2P orbital above and below plane of C atoms.
        • e- in p orbital of C overlaps with other C. Ring of e- density above +below plane of C atoms.
        • Overlap: pi-bonds spread over all 6C. They are delocalised.
        • So, Benzene doesn't decolourise Br water, react with HCl or the halogens.
      • Benzene's Reactions
        • Nitration
          • Benzene reacts with NO2+ conc. sulfuric acid at 50C
          • (HNO3) +
            • (H2SO4)
              • --->
                • (NO2+) +
                  • (HSO4-) +
          • (H+) +
            • (HSO4-)
              • ---->
                • (H2SO4)
        • Halogenation
          • (FeBr4-)+(H+) ----------> (FeBr3)+(HBr)
      • Reactivity of Benzene
        • Benzene
          • Only decolourises Br water with halogen carrier.
        • Cyclohexene
          • Decolourises Br water
    • Phenol
      • Phenols' Reactions
        • Sodium Hydroxide
          • Produces C6H5O-Na+ and H20
        • Partially dissociates in water- weak acid.
          • Produces C6H5O- and H+
        • Sodium
          • 2x Produces 2C6H5O-Na+ and H2
      • Ease of Bromination
        • Undergoes electrophilic substitution with Br with out halogen carrier.
        • More reactive than benzene due to lone pair of e-on O
        • Higher e- density activates ring, polarising Br so attract more strongly than benzene.
      • Uses
        • Synthesis of aspirin
        • Resins
        • Explosives
        • Antiseptics

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