A Graduate Student Is Cleaning Out the Refrigerator in the Laboratory

Essay

A graduate student is cleaning out the refrigerator in the laboratory and stumbles upon an unlabeled beaker in the back. The IR analysis of the compound shows a large broad peak at 3300 cm^-1 and no other significant peaks. The electron ionization mass spectrum shows the molecular ion at m/z 100 at 15% relative abundance and an ion at m/z 101 with a 1% relative abundance. Propose a structure for the unknown compound. Hint: Start with the relative abundance data to determine the number of carbons in the molecule.