Abstract

In 1870–75 Markovnikov enunciatedan empirical Rule which generalized theregiochemical outcome of addition reactions tounsymmetrical alkenes. This Rule remaineduseful for about 75 years, until suchreactions came to be better understood inmechanistic terms. Thereafter the Rule couldbe deduced from principles of relativecarbocation stabilization and ceased to servean independent purpose. Nevertheless, mostorganic textbooks continue to cite it (oftenin a historically inaccurate, anachronisticway), thereby distracting student attentionfrom the underlying principles. This paperadvocates doing away with the Rule in organicchemistry textbooks and classrooms.