The mass spectrum of unknown compound A shows a molecular ion at m/z116 and prominent peaks at m/z87 and m/z101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane, and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm -1 in the IR spectrum and a weak maximum at 274 nm 1e = 162 in the UV spectrum. The mass spectrum > > > of B shows a molecular ion of m/z72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z87 and 101.
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