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Was Markovnikov's Rule an Inspired Guess?

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Peter Hughes

Westminster School, London SW1P 3PB, United Kingdom

J. Chem. Educ., 2006, 83 (8), p 1152

DOI: 10.1021/ed083p1152

Publication Date (Web): August 1, 2006

Section:

History, Education, and Documentation

Abstract

Although Markovnikov's rule was formulated in 1870, its importance was not recognized for another 60 years. It has been suggested that this was because he published mainly in Russian, but more likely reasons were the experimental problems inherent in carrying out the addition of hydrogen halides to alkenes under controlled conditions, and subsequent analysis of the reaction products. In his 1870 article, there is very little convincing experimental evidence for his rule so that it was more of an inspired guess than a rational conclusion. A study of the contemporary literature shows that neither Markovnikov nor any of his contemporaries actually carried out the reactions often attributed to him, namely the addition of hydrogen bromide or hydrogen chloride to propene.