Q45 E - Organic Chemistry (Mcmurry)

Question

The sex attractant given off by the common housefly is an alkene named muscalure. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure?

Muscalure

Step-by-Step Solution

Answer

The answer is,

Reaction synthesis

Step 1: Reaction Synthesis

The reaction synthesis of any particular compound can be done using different synthetic reagents appropriate for the particular synthesis. The compound muscalure  is an alkene composed of an acetylene and an alkyl halide.

Step 2: Explanation

The synthesis of muscalure from the acetylene and alkyl halide is as shown below.

Reaction synthesis

The octyne is treated with sodamide followed by a reaction with the bromine compound to give an alkyne. The produced alkyne undergoes reduction with hydrogen and Lindlar’s reagent to give alkene, muscalure.