Chapter 9, Problem 33P

$\left(\text{Z}\right)\text{-9-tricosene}$

$\left[\left(\text{Z}\right){\text{-CH}}_3{\left({\text{CH}}_2\right)}_7\text{CH=CH}{\left({\text{CH}}_2\right)}_{12}{\text{CH}}_3\right]$

is the sex pheromone of the female housefly. Synthetic $\left(\text{Z}\right)\text{-9-tricosene}$ is used as bait to lure male flies to traps that contain insecticide. Using acetylene and alcohols of your choice as starting materials, along with any necessary inorganic reagents, show how you could prepare $\left(\text{Z}\right)\text{-9-tricosene}$.