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Markovnikov productZoomA-Z

Subject - Organic Chemistry

The rule formulated in 1869 by V.V. Markovnikov (also Markownikoff) predicts the products of an electrophilic addition of asymmetrical reagents (e.g. hydrogen halides, water and alcohols) to asymmetric alkenes. It states that the reaction favors the formation of the regioisomer in which the more nucleophilic part of the reagent (e.g. halogen) has been added to the carbon atom of the double with the least hydrogens. The reason for this is stabilization of the intermediate carbenium ion. The opposite is observed, for example, with electron attracting substituents (missing stabilization of the carbenium ion) or in radical reactions. In these cases, the resulting favored product is called anti-Markovnikov product.

Fig.1
Markovnikov- and anti-Markovnikov product

See also: Markovnikov rule