Antimarkovnikov Addition: Regioselective Functionalization of Alkenes in Organic Chemistry.

antimarkovnikov addition

1) B2H6, THF2) H202, OH-adds on OH to double bonded C (C then becomes single bonded)

Antimarkovnikov addition refers to a type of addition reaction in organic chemistry, in which the addition of a reactive species occurs at the less-substituted carbon of a carbon-carbon double bond. This is in contrast to Markovnikov addition, which involves the addition of a reactive species at the more-substituted carbon of a carbon-carbon double bond.

The most common example of antimarkovnikov addition is the addition of hydrogen bromide (HBr) to an alkene in the presence of a peroxide. The peroxide initiates a free-radical chain reaction that leads to the formation of a bromine radical. This radical adds to the alkene, and the resulting intermediate radical abstracts a hydrogen atom from the peroxide to form a second bromine radical. The second bromine radical adds to the alkene at the less-substituted carbon, resulting in the formation of the less-substituted alkyl bromide product.

Antimarkovnikov addition reactions can also occur with other electrophilic reagents, such as halogens, boranes, and organometallic compounds. In general, these reactions require the use of special catalysts or reaction conditions to achieve the desired selectivity. The ability to control the regioselectivity of alkene additions is an important tool for synthetic organic chemists, as it allows them to selectively functionalize specific positions within a molecule.

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