4C - Haloalkanes

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  • Created by: Strelly22
  • Created on: 29-03-21 11:54
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  • 4C - Haloalkanes
    • Definitions
      • Electronegativity
        • the measure of the attraction of a bonded atom for the shared pair of electrons in a covalent bond
      • Hydrolysis
        • a chemical reaction involving water or an aqueous solution of an hydroxide that causes the breaking of a bond in a molecule
      • Reflux
        • the continual boiling and condensing of a reaction mixture back to original container to ensure that the reaction takes place without the contents of the flask boiling dry
      • Nucleophile
        • an electron pair donor
    • Introduction to haloalkanes
      • to classify a haloalkane, consider the carbocation that would be formed if the halogen atom was left as a halide ion
        • primary = 2Hs
        • secondary = 1H
        • tertiary = 0Hs
      • Boiling Points
        • alcohol > 1-chloroalkanes > alkanes
        • 2-chloropropane < 1-chloropropane as smaller contact area ? LF weaker ? less energy
    • Reactivity of haloalkanes
      • haloalkanes > alkanes
        • C-X weaker than C-H so breaks more easily, allowing haloalkanes to react
          • except C-F
      • preparation of a alcohol by hydrolysis of a haloalkane
        • reagent: aqueous NaOH
        • conditions: heat under reflux
      • organic reactions require heating under reflux as they have simple molecular structures ? relatively low bp compared to ionic compounds such as salts
    • Rate of hydrolysis of haloalkanes
      • iodo > bromo > chloro
      • hot water speeds up the reaction
      • AgNO3 (aq): provides the water + traps the halide ion by forming a precipitate
      • ethanol was used as a co solvent
      • rate of reaction was compared by by timing how long it took for a visible quantity of silver halide precipitate
    • Uses of haloalkanes
      • tetrafluoroethene
        • TFE
        • 'Teflon', non stick cookware
      • dichlorodifluoromethane
        • Freon-12
        • refrigerant, aerosol spray propllent (silly string)
      • trichloroethene
        • TCE
        • solvent, anaesthetic
      • trichloromethane
        • chloroform
        • (anaesthetic), precursor to other organic products
      • 2-bromo-2-chloro-1,1,1-trifluoromethane
        • Halothane
        • general anaesthetic
      • bromotrifluoromethane
        • Halon 1301
        • fire extinguishers
      • poly-chloroethene
        • PVC
        • plastic pipes, electrical cable insulation, waterproof clothing
      • poly(tetra-fluoroethene)
        • Teflon
        • coating on non-stick cookware
      • chlorodifluoromethane
        • HCFC-22
        • propellant and refrigerant
      • 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane
        • DDT
        • insecticide
    • CFC's and the Ozone Layer
      • Ozone
        • outer edge of stratosphere
        • ozone formed
          • 1) O2 + uv ? 2O.
          • 2) O2 + O. ? O3
        • ozone broken down
          • O3 + uv ? O2 + O.
        • photodissociation of CFCs causes chlorine radicals (initiation)
          • CF2Cl2. ?CF2Cl. + Cl.
          • homolytic fission
          • uv light required
          • O3 + O ? 2O2 overall
          • Cl is a catalyst
        • NO breaks down ozone (propagation)
          • from lightening strikes and high flying aircraft
          • O3 + O ? 2O2 overall
          • homogenous as catalysts and reactants in the same phase
      • CFCs
        • chlorofluorocarbon
        • hydrochlorofluorocarbon
        • refrigerants + aerosol spray propellants

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