Chapter 13, Problem 13.54P

Reaction of ${\text{BrCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ with $\text{NaH}$ forms compound $W$, which

gives the IR and mass spectra shown below. Propose a structure for $W$ and draw

a stepwise mechanism that accounts for its formation.