Question: A compound A has a strong, broad IR absorption at 3200-3500 cm-1 and the proton NMR spectrum shown in Fig. P13.48a. Treatment of compound A

A compound A has a strong, broad IR absorption at 3200-3500 cm-1 and the proton NMR spectrum shown in Fig. P13.48a. Treatment of compound A with H2SO4 gives compound B, which has the NMR spectrum shown in Fig. P13.48b and a molecular ion at m/z = 84 in its El mass spectrum. Identify compounds A and B,
Fig. P13.48

chemical shift, Hz 24002100 1800 500 1200 900 600 300 0 8966 compound A disappears after 1595446 D2O shake chemical shift, ppm (5)

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