How to convert 1 propyne to 2 bromo propane
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method 1: propyne + H2 on Pt catalyst => propane. then do free radical halogenation with Br2, which will prefer to add to the most substituted carbon atom, giving 2-bromopropane
method 2: propyne + H2 on poisoned catalyst (ex Lindlar's) => propene. next do oxymecuration/demercuration (which tends to give you the more substituted alcohol) to yield isopropanol. next, brominate with HBr or P + Br2 or PBr3, etc to yield 2-bromopropane.
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