Chapter 20, Problem 45P

Compound W $\left(C_{15}{H}_{17}N\right)$ is soluble in dilute aqueous HCI and exhibits no peaks in the 3300-3500 $c{m}^{-1}$ region of its IR spectrum. The ${}^{1}H$ NMR spectrum of W is shown in Fig. 20.6. Propose a structure for W.

Figure 20.6 The ${}^{1}H$ NMR spectrum of compound W, Problem 20.45 Expansions of the signals are shown in the offset plots.