Rebecca Smith, Kendra Rick, Theresa Herbers

 

Proposed Synthesis of Compound C

 

We started with an alkyl bromide.  A Mg ion was inserted into the C-Br bond through a reaction in THF1, enabling the compound to react with an epoxide7 containing a bromide attachment.  This formed an aldehyde,2 which was then reacted with another alkyl bromide2 to form an 8-carbon chain with a hydroxide group attached to the fourth carbon.  Reaction with KO-t-Bu in EtOH2 eliminated the hydroxide group, creating 3-octene.