Proposed Synthesis for Compound C

 

Bryan Cole

 

1.      First, bromoethane reacts with NaC₂H to form a 4-carbon terminal alkyne.

2.      This reacts with sodium in liquid nitrogen to form a terminal alkene

3.      This reacts with a Br-radical, in the presence of peroxide, to add a bromine to the end of the chain, in the anti-Markovnikov fashion.

4.      This will react in the same manner as the first reaction to form a 6-carbon terminal alkyne.

5.      We can react this alkyne with NaNH₂ and bromoethane to form 3-octyne.

6.      In the last step, we convert the triple bond to a trans double bond by using sodium in liquid ammonia.