In —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, anachronisticwaythereby distracting student attentionfrom the underlying principles. This paperadvocates doing away with the Rule in organicchemistry textbooks and classrooms. This is a preview of subscription content, log in via an institution to check access. Rent this article via DeepDyve. Institutional subscriptions. Baeyer, Ueber das Neurin. Annalen der Chemie und Pharmacie —, Google Scholar. Bays, S. Blumer, S. Baral-Tosh, D. Behar and P. Neta, Intramolecular Electron Transfer and Dehalogenation of 333 rule dating Anion Radicals. Journal of the American Chemical Society —, Bohlmann, N. Ottawa and R. Brown and B. Subba Rao, Hydroboration. The Reaction of Olefins with Sodium Borohydride-Aluminum Chloride. A Convenient Route to Organoboranes and the anti-Markownikoff Hydration of Olefins. See also H. Brown, Hydroboration. New York: Benjamin, Bruice, Organic Chemistry3rd edition, pp. Englewood Cliffs, NJ: Prentice Hall, Butlerov, Mittheilungen aus dem 333 rule dating Universitätslaboratorium zu Kasan. Isomerie der gesättigten Kohlenwasserstoffe C4H10 und der Butylene C4H8. Isobutylalkohol der primäre Pseudobutylalkohol oder Pseudopropylcarbinol. Annalen der Chemie und Pharmacie 1—32, Conant and A. Blatt, The Chemistry of Organic Compounds4th edition, pp. New York: Macmillan, Decker, Wladimir Wasiliewitsch Markownikow. Berichte der deutschen chemischen Gesellschaft —, Fieser and M. Fieser, Organic Chemistrypp. Heath, Fox and J.
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