Rebecca Smith, Kendra Rick, Theresa Herbers

 

 

 

Proposed Synthesis of Compound A

We begin our synthesis with 1-bromo-propane, which is reacted with Mg in tetrahydrofuran1 to insert the Mg between the alkyl group and the bromide ion.  This makes it available to react with a ketone2 to form a C-C bond, producing a longer carbon chain, 2-methyl-2-pentanol.  Since -OH is a poor leaving group, the alcohol is reacted with TsCl in pyridine3 to substitute a tosyl group for the hydroxide.  The tosyl group leaves easily in the polar aprotic solvent DMSO4 and is substituted by fluoride.  In order to get an anti-Saytzeff product, the alkyl fluoride is reacted with NaOCH₃ in methyl alcohol5 to produce the less substituted alkene.