I am trying to accomplish an assignment involved in completing multi-step syntheses reactions, by filling in reaction conditions on the white boxes on top of the reaction arrows and drawing what the products would be in the template boxes.
This question is attached. I'm asking for some tips if anyone can give some. I can use addition, elimination, substitution and if applicable, alcohol chemistry.
For the first step, I was thinking of doing an E2 elimination (Zaitsev - using NaOMe and [Δ] as the reaction conditions) to acquire a double bond across carbon 2 and carbon 3 to get rid of the bromine. From there (this is where I can really use a tip), I was thinking of doing a hydrohalogenation reaction (H-Cl) across the double bond, but I don't think that would do anything for me in the later steps (from there I said I can do another elimination reaction, then another hydrohalogenation, BUT that won't work since it will add chlorine to the more substituted carbon).