When phenyl isothiocyanate, C6H5N == C == S, is reduced with lithium aluminum hydride, the product formed has these spectral data:
MS (m/z): 107, 106
IR (cm-1): 3330 (sharp), 3050, 2815, 760, 700
1H NMR (δ): 2.7 (s, 3H), 3.5 (broad, 1H), 6.6 (d, 2H), 6.7 (t, 1H) 7.2 (t, 2H)
13C NMR (δ): 30 (CH3), 112 (CH), 117 (CH), 129 (CH), 150 (C)
(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.)