I can use any other starting materials I\'d like. I\'ve tried a few different wa

Question

I can use any other starting materials I'd like. I've tried a few different ways, one of them being halogenating the butadiene with concentrated br2 in exremely low temperatures. resulting in a 1,2 adduct of the br2 being the major product, then using a phenyl-mgbr compound to attack Br on the terminal end. followed up with EtONA/EtOH. but the problem with this is that I think the phenyl mgbr would attack both Br.

Thanks

Explanation / Answer

1) 1, 3 butadiene + Br2 ( low temp) ----> 3, 4 dibromo 1 butene ( 1,2 product forms at low temp) 2) 3,4 dibromo 1 butene + excess NaNH2 ----> CH2=CH-CC-Na ( where CC means C triple bond C) , 3) CH2=CH-CCNa + PhBr ----> CH2=CH-CC-Ph , 4) CH2=CH-CC-Ph + Na/NH3 ---> 1 phenyl 1, 3 butadiene , here Na/NH3 reduces alkynes to alkenes but not alkenes.

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