Bromination propyl benzene

[cj]

I'm just getting stumped on how to go on this one. I'm supposed to draw the major organic product formed at each step.

 

A) I figure the bromine is added but can't decide where. I think it would go on the propyl chain but am not sure.

 

B) Second part I see as an E2 reaction forming a double bond wherever the bromine is removed from.

 

C) Third part I thought those were were used to break a triple bond and insert a double bonded O as well as some H. But of course I've formed no triple bonds anywhere.

 

So as you can see, I'm just all lost

 

 

[amit]

in first step free radical will be generated hence substitution on aromatic ring is unlikely. Br radical would prefer secondry position on propyl chain ie at position 3 (numbering the c attached to ring as 1) as then radical formed will have resonance stablizing effect of phenyl ring. i also think second step is formation of double bond. third one is hydro boration reaction with introduction of alcohol