Chapter 11, Problem 11.18P

Show how $\text{HC}\equiv \text{CH}$, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{Br}$ and ${\left({\text{CH}}_{\text{3}}\right)}_2{\text{CHCH}}_2{\text{CH}}_2\text{Br}$ can be used to prepare ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{C}\equiv {\text{CCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{CH}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}$. Show all the reagents and use curved arrows to show movement of electron pairs.