The conversion of propene to 2-bromo propane is carried out with HBr. Addition is according to Markownikoff's rule. Bromine is added to more substituted C atom.
The conversion of propene to 1-bromo propane is carried out with HBr in presence of peroxide. Addition is contrary to Markownikoff's rule. Bromine is added to less substituted C atom.
The conversion of propene to 3-bromo-1-propene is carried out with NBS. This is an example of allylic bromination.
The conversion of propene to 1,2-dibromopropane is carried out with NBS.