Measuring the rate of hydrolysis

• Acidified aqueous silver nitrate can be used to measure the rate of hydrolysis of halogenoalkanes
• The following method is used:
  • Set up three test tubes in a 50?oC water bath, with a mixture of ethanol and acidified silver nitrate
  • Add a few drops of a chloroalkane, bromoalkane and an iodoalkane to each test tube and start a stop watch
  • Time how long it takes for the precipitates to form

• Reacting halogenoalkanes with?aqueous silver nitrate solution?will result in the formation of a?precipitate
• The?rate of formation?of these precipitates can also be used to determine the reactivity of the haloalkane

Haloalkane Precipitates Table

• The precipitates will form as the reaction progresses and the halide ions are formed
  • The yellow silver iodide precipitate is the fastest?nucleophilic substitution?reaction
    • This is because the C-I bond has the lowest bond enthalpy, so it is the easiest to break and will cause the I-?ions to form the fastest
  • The white chloride precipitate is the slowest nucleophilic substitution reaction
    • This is because the C-Cl bond has the highest bond enthalpy, so it is the hardest to break and will cause the Cl-?ions to form the slowest

• • Silver fluoride is soluble, so a precipitate will not be formed in this reaction
• This confirms that fluoroalkanes are the least reactive and iodoalkanes are the most reactive halogenoalkanes
  • It can be predicted that the formation of silver astatide would be even quicker than silver iodide

The trend in reactivity of haloalkanes