antiMarkownikowAddition

Anti-Markownikoff addition, also known as anti-Markownikoff reaction, is a chemical reaction in which the nucleophile attacks the less substituted carbon of a carbonyl compound, contrary to the Markownikoff rule. This rule, named after the Russian chemist Vladimir Markovnikov, states that in the addition of a protic acid (HX) to an alkene, the hydrogen atom attaches to the carbon atom with the greater number of hydrogen atoms, and the halogen atom attaches to the carbon atom with the fewer hydrogen atoms. However, in anti-Markownikoff addition, the nucleophile prefers to attack the less substituted carbon, leading to a different product than predicted by the Markownikoff rule.

Anti-Markownikoff addition is often observed in reactions involving strong nucleophiles and electron-withdrawing groups on the carbonyl compound. The reaction mechanism typically involves the formation of a tetrahedral intermediate, followed by the departure of a leaving group to form the final product. The stereochemistry of the product can also be influenced by the anti-Markownikoff addition, leading to the formation of different isomers.

Anti-Markownikoff addition is an important concept in organic chemistry, as it allows for the synthesis of a wide range of compounds with different functional groups and stereochemistries. It is also a useful tool for understanding the reactivity of carbonyl compounds and the factors that influence their behavior in chemical reactions.