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IB Chemistry Power Points

                               Topic 20
                          Organic Chemistry
www.pedagogics.ca




              Substitution Reactions
SN2 Nucleophilic Substitution - Review
 Recall: nucleophilic substitution of a bromoalkane




Reaction occurs when
bromoethane is added to a
dilute NaOH solution.
SN2 Reaction with Cyanide ions
Bromoethane + CN- ions (KCN, reflux in methanol) - mechanism




Overall
SN2 Reaction with Cyanide ions
Product is a nitrile




                       propanenitrile
SN2 Reaction with ammonia
Bromoethane + NH3 (concentrated, pressure) - mechanism




Cation donates proton to another NH3
SN2 Reaction with ammonia
For IB – The overall reaction is considered to be




 Product is also a nucleophile
2o and 3o amines are formed
Effect of nucleophile on rate of
substitution
The electron density of the nucleophile affects the rate of
substitution.
- Anions are more reactive than neutral molecules.

Reactivity depends on how easily the nucleophile can
donate electrons
- N is less electronegative than O



            Rate of Reaction

   CN- > OH- > NH3 > H2O
Effect of R-X on rate of substitution
Rate of substitution is fastest when the leaving halide ion
is iodine and slowest when the leaving halide ion is
fluorine. WHY?
Effect of R-X on rate of substitution
Rate of substitution depends on whether the
halogenoalkane is primary, secondary or tertiary.




                         1o
     Rate of SN2                   Rate of SN1
     Reaction            2o        Reaction
     Increases                     Increases
                         3o
Effect of nucleophile on rate of
substitution
The concentration of the nucleophile affects the rate of
SN2 substitution but not SN1.
Topic 20 2    substitution reactions

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Topic 20 2 substitution reactions

  • 1. IB Chemistry Power Points Topic 20 Organic Chemistry www.pedagogics.ca Substitution Reactions
  • 2. SN2 Nucleophilic Substitution - Review Recall: nucleophilic substitution of a bromoalkane Reaction occurs when bromoethane is added to a dilute NaOH solution.
  • 3. SN2 Reaction with Cyanide ions Bromoethane + CN- ions (KCN, reflux in methanol) - mechanism Overall
  • 4. SN2 Reaction with Cyanide ions Product is a nitrile propanenitrile
  • 5. SN2 Reaction with ammonia Bromoethane + NH3 (concentrated, pressure) - mechanism Cation donates proton to another NH3
  • 6. SN2 Reaction with ammonia For IB – The overall reaction is considered to be Product is also a nucleophile
  • 7. 2o and 3o amines are formed
  • 8. Effect of nucleophile on rate of substitution The electron density of the nucleophile affects the rate of substitution. - Anions are more reactive than neutral molecules. Reactivity depends on how easily the nucleophile can donate electrons - N is less electronegative than O Rate of Reaction CN- > OH- > NH3 > H2O
  • 9. Effect of R-X on rate of substitution Rate of substitution is fastest when the leaving halide ion is iodine and slowest when the leaving halide ion is fluorine. WHY?
  • 10. Effect of R-X on rate of substitution Rate of substitution depends on whether the halogenoalkane is primary, secondary or tertiary. 1o Rate of SN2 Rate of SN1 Reaction 2o Reaction Increases Increases 3o
  • 11. Effect of nucleophile on rate of substitution The concentration of the nucleophile affects the rate of SN2 substitution but not SN1.