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Elimination by the E1 mechanism

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  • Just as there were two mechanisms for nucleophilic substitution, there are two elimination mechanisms.


    The E1 mechanism is nearly identical to the SN1 mechanism, differing only in the course of reaction taken by the carbocation intermediate. As shown by the following equations, a carbocation bearing beta-hydrogens may function either as a Lewis acid (electrophile), as it does in the SN1 reaction, or a Brønsted acid, as in the E1 reaction.

    Thus, hydrolysis of tert-butyl chloride in a mixed solvent of water and acetonitrile gives a mixture of 2-methyl-2-propanol (60%) and 2-methylpropene (40%) at a rate independent of the water concentration. The alcohol is the product of an SN1 reaction and the alkene is the product of the E1 reaction. The characteristics of these two reaction mechanisms are similar, as expected. They both show first order kinetics; neither is much influenced by a change in the nucleophile/base; and both are relatively non-stereospecific.

    (CH3)3CCl + H2O ——> [ (CH3)3C(+) ] + Cl(–) + H2O ——> (CH3)3COH + (CH3)2C=CH2 + HCl + H2O

    To summarize, when carbocation intermediates are formed one can expect them to react further by one or more of the following modes:

    1. The cation may bond to a nucleophile to give a substitution product.
    2. The cation may transfer a beta-proton to a base, giving an alkene product.
    3. The cation may rearrange to a more stable carbocation, and then react by mode #1 or #2.

    Since the SN1 and E1 reactions proceed via the same carbocation intermediate, the product ratios are difficult to control and both substitution and elimination usually take place.