Elimination Reaction - E2 and E1 Elimination Final Notes

E2 and E1 Elimination Final Notes

The reaction rate is influenced by halogen's reactivity; iodide and bromide being favored. Fluoride is not a good leaving group. There is a certain level of competition between elimination reaction and nucleophilic substitution. More precisely, there are competitions between E2 and SN2 and also between E1 and SN1. Substitution generally predominates and elimination occurs only during precise circumstances. Generally, elimination is favored over substitution when

  • steric hindrance increases
  • basicity increases
  • temperature increases
  • the steric bulk of the base increases (such as in Potassium tert-butoxide)
  • the nucleophile is poor

In one study the kinetic isotope effect (KIE) was determined for the gas phase reaction of several alkyl halides with the chlorate ion. In accordance with a E2 elimination the reaction with t-butyl chloride results in a KIE of 2.3. The methyl chloride reaction (only SN2 possible) on the other hand has a KIE of 0.85 consistent with a SN2 reaction because in this reaction type the C-H bonds tighten in the transition state. The KIE's for the ethyl (0.99) and isopropyl (1.72) analogues suggest competition between the two reaction modes.

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