Wednesday, 3 June 2015

2.10.2b: interpret given data and observations comparing the reactions and reactivity of primary, secondary and tertiary compounds

Tertiary reacts almost instantly
Secondary reacts more slowly
Primary takes a considerable amount of time to react
Why do tertiary halogenoalkanes hydrolyse the fastest?:
  • the three alkyl groups donate electron density to the carbon atom, which makes the C-X bond weaker, so it breaks first, regardless of OH- concentration
  • therefore, the weaker the C-X bond, the faster the reaction
  • substitution of a tertiary halogenoalkane (INSERT MECHANISM HERE)

electronegativity
I < Br < Cl < F
bond length
C-F < C-Cl < C-Br < C-I
bond strength
C-I < C-Br < C-Cl < C-F
molecular size
F < Cl < Br < I

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