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Addition to Alkenes

Markovnikov vs anti-Markovnikov - the regiochemistry rule and its exceptions.

A free, animated addition to alkenes you can read here or embed on any website, from Scrollchart.

Addition to Alkenes

Addition to AlkenesHBr regiochemistry: Markovnikov (ionic) vs anti-Markovnikov (radical, peroxide)Markovnikov AdditionHBr, no peroxide (ionic)anti-Markovnikov AdditionHBr + ROOR peroxide (radical)

HBr addition to propene: H goes on the more H-rich carbon, Br on the more substituted (Markovnikov). Peroxide reverses regiochemistry (anti-Markovnikov).

Good for

  • Teaching Markovnikov's rule and its mechanistic basis via carbocation stability in undergraduate organic chemistry
  • Contrasting ionic and radical addition mechanisms using the same substrate (propene + HBr)
  • Explaining how reaction conditions (presence or absence of peroxides) determine product regiochemistry

Source & accuracy

This addition to alkenes is an editorial illustration built to represent the concept accurately. Where it shows figures, they are typical or representative values chosen to make the relationship clear, not a single underlying dataset. The diagram and its explainer are reviewed and maintained centrally, and updated over time as understanding improves.

Markovnikov's rule and the carbocation

When a protic acid such as HBr adds across an asymmetric alkene, Markovnikov's rule predicts the hydrogen attaches to the carbon that already has more hydrogens, placing the halide on the more substituted carbon. The reason is the intermediate carbocation: the reaction proceeds through the more stable carbocation, which is the more substituted one because alkyl groups donate electron density.

The classic shorthand, the rich get richer, summarizes the outcome but the carbocation stability argument is the actual driver.

Anti-Markovnikov exceptions

Adding HBr in the presence of peroxides reverses the regiochemistry. This radical mechanism, the peroxide effect described by Kharasch, proceeds through the more stable radical rather than a cation, so the bromine ends up on the less substituted carbon. Hydroboration-oxidation also gives anti-Markovnikov alcohols because boron adds to the less hindered carbon.

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Reference

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A free, embeddable, animated addition to alkenes for any website.
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