MARKOVNIKOV'S RULE IN HISTORY AND PEDAGOGY


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Abstract

In 1870–75 Markovnikov enunciated an empirical Rule which generalized the regiochemical outcome of addition reactions to unsymmetrical alkenes. This Rule remained useful for about 75 years, until such reactions came to be better understood in mechanistic terms. Thereafter the Rule could be deduced from principles of relative carbocation stabilization and ceased to serve an independent purpose. Nevertheless, most organic textbooks continue to cite it (often in a historically inaccurate, anachronistic way), thereby distracting student attention from the underlying principles. This paper advocates doing away with the Rule in organic chemistry textbooks and classrooms.

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