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How can I illustrate antimarkovnikov's rule by the addition of hydrogen bromide to propene in the presence of benzoyl peroxide?
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.
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.
The 2° radical reacts with another HBr molecule to produce 1-bromopropane and a bromine radical to continue the process.
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.