ARENES

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  • Created by: Katie
  • Created on: 15-03-13 10:25
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  • ARENES
    • Benzene
      • Structure
        • Kekule suggested that benzene was a cyclic structure with alternating single and double bonds. BUT!!
          • 1.It did not readily go under electrophilic addition
          • 2. C-C bonds in benzene are an intermediate length between long C-C single bonds and short C=C bonds
          • 3.Enthalphy of hydrogenation was less exothermic than expected
        • Delocalised system
          • Each Carbon has 4 electrons in its outer shell, 3are used to form sigma bonds. The 4th isinth sin the 2p orbital.
            • The p orbital overlaps sideways with the neighbouring 2p orbitals, creating a ring of delocalised electrons above and below the carbon ring, creating  a system ofpi bonds spread over all 6 carbons
      • Properties
        • colourless at RTP
        • Carcinogen
      • Reactions
        • Nitration C6H6+HNO3 -->               C6H5NO2+ H2O          Conc nitric acid, Conc sulphuric acid, reflux at 55oC
          • Reduction of nitrobenzene C6H5NO2 +6[H] ----> C6H5NH2 +2H2O         Tin and Conc sulphuric acid Reflux
            • Diaziation of phenylamine C6H5NH2+ HNO2+HCl -----> C6H5N2Cl + 2H2O Nirtous acid and HCl below 10oC
              • Substitution    C6H5N2Cl +H2O ---> C6H5OH +N2+Cl. Above 10oC
                • Phenol
                  • Properties
                    • Colourless, Cyrystaline
                  • Uses
                    • Use in plastics, antiseptics, disinfectants, resins
                  • Reactions
                    • Acts as a weak acid , releases the H+ from the OH group
                    • Reacts with NAOH to form a salt and Water
                    • Reacts with NA(s) to form an ionic salt and Hydrogen
                    • With Bromine without a catalyst, multi-substitution. Orange solution--> white ppt
              • Coupling C6H5N2Cl + C6H5OH +NaOH -->C6H5-N=NC6H4)H +NaCl +HCl  Alkaline solutin below 10oC
    • Phenol
      • Properties
        • Colourless, Cyrystaline
      • Uses
        • Use in plastics, antiseptics, disinfectants, resins
      • Reactions
        • Acts as a weak acid , releases the H+ from the OH group
        • Reacts with NAOH to form a salt and Water
        • Reacts with NA(s) to form an ionic salt and Hydrogen
        • With Bromine without a catalyst, multi-substitution. Orange solution--> white ppt

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