Rebecca Smith, Kendra Rick, Theresa Herbers

 

Proposed Synthesis of Compound E

 

 

We began with a reaction of 1-propyne with Na⁺, which deprotonated the alkyne to form an acetylide ion which then added to an ethyl group9.  The resulting alkyne was converted to a cis alkene through a hydrogenation reaction with Lindlar’s catalyst10.  The alkene was treated with Br₂ in the presence of water11 which caused a halohydrogenation reaction to take place, simultaneously adding a hydroxide and a bromide group to the compound.  This would cause two constitutional isomers to be formed, but only the desired one is shown here.  It would be impossible to have a completely regioselective reaction because both the –OH and the Br- are adding to secondary carbons, therefore there is no difference in molecular stability that would cause either group to add preferentially to a certain carbon.  The hydroxide group was removed by reacting it with H₂SO₄ and water2.  The bromide group in the resulting alkene was activated with a Mg/THF reaction1.  Through a final reaction with a 3-carbon aldehyde2, we obtained 4-methyl-3-hepten-5-ol, also known as COMPOUND E!!!!