anti-Markovnikov

Halogen avoids carbon

Anti-Markovnikov describes a chemical reaction pattern where an added group attaches to the more substituted carbon of a double bond—the opposite of the usual Markovnikov rule.

In organic chemistry, this typically occurs in certain radical reactions or hydroboration: The anti-Markovnikov addition placed the hydroxyl group on the terminal carbon.

The term honors Russian chemist Vladimir Markovnikov by naming what violates his rule.

mechanism

alkene

Doubly-bonded carbon compound

borane · oxidation · rearrangement · selectivity · intermediate · propagation · initiation · stereochemistry · concerted

synthesis

alcohol

Intoxicating hydroxyl compound

strategy · target · pathway · yield · product · industrial · pharmaceutical · methodology · route · precursor

teaching

rule

Governing principle or standard

prediction · problem-solving · mechanism · undergraduate · synthesis · reaction · curriculum · laboratory · tutorial · mnemonic

Categories
Opposites
regioselectivity in addition reactions

anti-MarkovnikovMarkovnikov

Alkene addition regiochemistry predictor

Family

Markovnikov

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Used worldwide · Timeless · Abstract · Rated G