In the steps of Markovnikov
The addition reactions of HCl and HBr to propene to give either 2-chloropropane or 2-bromopropane are often given as examples of Markovnikov's Rule, but in his original 1870 paper, Markovnikov used HI and not HBr or HCl.
There are no experimental details in Markovnikov's paper to show that he (or anyone else) had actually reacted HCl/HBr with propene. He does comment though that these hydrogen halides had been used by other workers, for example Reboul who claimed to have reacted HBr with acetylene to give the first vinyl bromide and then 1,1-dibromoethane.2 This lack of experimental detail prompted us to see if we could bring about and analyse the products of the propene/HI reaction by using only the methods available to Markovnikov at that time.
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