How can I illustrate antimarkovnikov's rule by the addition of hydrogen bromide to propene in the presence of benzoyl peroxide?

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Answer 1 · 2015-06-13T17:42:09

You write the mechanism for the reaction.

This is a free radical reaction, so it has initiation, propagation, and termination steps.

Initiation

The chain is initiated by free radicals produced by cleavage of an #"O-O"# bond in the benzoyl peroxide.

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The benzoyl radicals extract a hydrogen atom from an #"HBr"# molecule to produce bromine radicals.

#"PhCOO·" + "H-Br" →"PhCOOH" + "·Br"#

Propagation

The bromine radical adds to the propene to form the more stable 2° radical.

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The 2° radical reacts with another HBr molecule to produce 1-bromopropane and a bromine radical to continue the process.

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Termination

Eventually two free radicals hit each other and produce a molecule of some sort.

#"Br·" + "·Br" → "Br"_2#

#"CH"_3"-" stackrel(·)("C")"H-CH"_2 "-Br" + "·Br" → "CH"_3"-CHBr-CH"_2"-Br"#

#"2CH"_3"-" stackrel(·)("C")"H-CH"_2 "-Br" → "Br-CH"_2"-CH(CH"_3")-CH(CH"_3")-CH"_2"-Br"#

The process stops here because no new free radicals are formed.