9. The 'H-NMR spectrum of Compound A (C10H13NO2) is given below with integration indicated. When A is warmed with aqueous NaOH it yields an amine, Compound B(C3H11NO). The 'H-NMR spectrum

of Compound B is almost identical to that of A except the signal at 2.1 ppm has disappeared and the broad signal at 7.9 ppm has moved to 3.4 ppm (also broad). When heated with HI the amine (Compound B) yields Compound C (C6H7NO) and its IR spectrum is shown below. Propose and draw structures of Compounds A, B, and C with rationale where appropriate. Consider the'H-NMR signal at 7.9 ppm in Compound A. Why does it appear at 3.4 ppm in Compound B. Explain why both signals are broad.