Unimolecular Nucleophilic Substitution - Elimination

These two mechanisms are based on two possible behaviors for a carbocation formed by unimolecular dissociation of a C-X bond. Hence they always occur together, and therefore are only infrequently useful for synthesis.

The carbocation intermediate means that the usual stereochemical result is racemization. However, in relatively non-polar solvents, ion pairs may lead to an excess of inversion. In E1 reactions the more substituted alkene always predominates.

Here is a decision tree [CLICK] that summarizes our rules for deciding when SN2, SN1-E1, and E2 will occur.

SN1-E1 is facilitated by polar protic solvents that strongly solvate the leaving group and aid ion separation.

One important rule is that SN1-E1 NEVER occurs at primary carbons.


This page last modified 1:06 PM on Monday August 15th, 2011.
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