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Chemical Education Today
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Letters
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Markovnikov's Rule
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Robert C. Kerber
Chemistry Department, State University of New York at Stony Brook, Long Island, NY 11794-3400
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July 2007
Vol. 84 No. 7
p. 1109
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| Full Text |
The recent contribution by Ilich, Rickertsen, and Becker (1) provides abundant reasons for abandoning the description of addition reactions and their products as “Markovniknov” or (even worse) “anti-Markovnikov”. In a recent review (2) I have surveyed the history of this usage and concluded that its use in teaching has long outlived its utility. The deeper understanding of these reactions as involving appropriate reactive intermediates (e.g., carbocations), whose relative stabilities can be understood on a general basis, should have superseded the use of an empirical rule that is often inapplicable, often restated in ways unrecognizable to its originator, and never an adequate substitute for understanding. If we wish students to understand organic reactivity as a whole, we should not provide them with this cognitive crutch. If our use of the description of one product as a “Markovnikov product” is meant to honor a great 19th century chemist, what is the effect of describing another as an “anti-Markovnikov product”? Unfortunately, the authors of the article draw back from the simple conclusion that the rule should be abandoned, but rather attempt once again to restate or reformulate it, while clinging to the name. In agreement with Gooch (3), I urge teachers and textbook authors to move past Markovnikov’s rule once and for all.Literature Cited- Ilich, P.-P.; Rickertsen, L. S.; Becker, E. J. Chem. Educ. 2006, 83, 1681–1685.
- Kerber, R. Foundations of Chemistry 2002, 4, 61–72.
- Gooch, E. E. J. Chem. Educ. 2001, 78, 1358–1359.
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| More Information |
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Citation |
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
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Keywords |
Addition Reactions; Misconceptions / Discrepant Events; Organic Chemistry; Reactions; Second-Year Undergraduate
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History |
Created:
Last Updated: |
5/29/2007
6/7/2007
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