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Elimination Reactions

E2 Mechanism

E2 Mechanism

The reaction occurs more readily if the H lost has some acidic character as in the following example.

More Acidic Hydrogen faster the reaction

The first reaction is faster since the base abstracts a proton from the benzylic carbon resulting in a stablised carbanion. The hydrogen at the bezylic carbon is thus more acidic than in the second example.

Note: The carbanion in the first case is stabilized by resonance participation of the adjacent phenyl ring. In the second case the anion is destabilized by the +I effect of the alkyl group, hence the anion may not be formed at all.

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Elimination and geometrical constraints

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Elimination E1 & E2
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