Chapter 20, Problem 52P

When phenyl isochiocyanatc, $C_6{H}_{5}N=C=S$, is reduced with lithium aluminum hydride, the product formed has these spectral data:

MS $\left(\text{m/z}\right)$: 107, 106

IR $\left(c{m}^{–1}\right)$: 3330(sharp), 3050, 2815, 760,700

${}^{1}H$ NMR $\left(\delta \right)$: $2.7\left(s,3H\right),3.5\left(broad,1H\right),6.6(\delta ,2H),6.7\left(t,1H\right)7.2\left(t,2H\right)$

${}^{13}C$ NMR $\left(\delta \right)$: $30\left(C{H}_3\right),112\left(CH\right),117\left(CH\right),129\left(CH\right),150\left(C\right)$

(a) What is the structure of the product?

(b) What is the structure that accounts for the 106 m/z peak and how is it formed? (It is an iminium ion.)