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An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism. Either the unsaturation of the molecule increases (as in most organic elimination reactions) or the valence of an atom in the molecule decreases by two, a process known as reductive elimination. An important class of elimination reactions are reactions involving alkyl halides or alkanes in general with good leaving groups, reacting with a Lewis base to form an alkene in the reverse of an addition reaction. When the substrate is asymmetric regioselectivity is determined by the Zaitsev's rule.The one and two-step mechanisms are named and known as E2 reaction and E1 reaction, respectively.
E2 mechanism In the 1920s, Sir Christopher Ingold proposed a model to explain a peculiar type of chemical reaction: the E2 mechanism. E2 stands for bimolecular elimination and has the following specificities. The reaction fundamental elements are An example of this type of reaction in scheme 1 is the reaction of isopropylbromide with potassium ethoxide in ethanol. The reaction products are isobutylene, ethanol and potassium bromide. E1 mechanism E1 is a model to explain a peculiar type of chemical elimination reaction. E1 stands for unimolecular elimination and has the following specificities. An example in scheme 2 is the reaction of tert-butylbromide with potassium ethoxide in ethanol. E1 eliminations happen with highly substituted alkyl halides due to 2 main reasons. E2 and E1 elimination final notes The reaction rate is influenced by halogens reactivity; iodide and bromide being favored. Fluoride is too reactive and its level of basicity too high. 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 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. Specific elimination reactions The E1cB elimination reaction is a special type of elimination reaction involving carbanions. In each of these elimination reactions the reactants have specific leaving groups: See also | ||||||||
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