What are SN1 and SN2 reactions?

SN1 and SN2 reactions are two possible mechanisms for nucleophilic substitution reactions. 

SN1 reaction

  • Occurs with tertiary halogenoalkanes. In these, the carbon atom bonded to the halogen atom is also bonded to three other carbon atoms (alkyl groups).
  • Mechanism: 
    1. The carbon–halogen bond breaks, forming a tertiary carbocation. This is an example of heterolytic fission as both electrons in the bond go to the halogen. 

    2.  The tertiary carbocation is immediately attacked by the hydroxide ion.
  • The rate of the reaction only depends on the concentration of the halogenoalkane only, as shown in the first (slow) step of the mechanism.
    rate = k[halogenoalkane]
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SN2 reaction

  • Occurs with primary halogenoalkanes. In these halogenoalkanes, the halogen atom is bonded to a carbon atom, which is bonded to one other carbon atom and two hydrogen atoms.
  • Mechanism: The nucleophile (OH-) donates a pair of electrons to the δ+ carbon atom, forming a new covalent bond. At the same time, the C─Br bond is breaking, with the Br atom taking both electrons in the bond. The Br atom leaves as a Br− ion.
  • This is an example of heterolytic fission of a covalent bond as Br takes both electrons in the C-Br bond.
  • The rate of the reaction depends on both the concentration of the halogenoalkane and the concentration of the hydroxide ions present.
    rate = k[halogenoalkane][OH-]
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