Chapter 12, Problem 38P

An unknown X shows a broad absorption band in the infrared at 3200-3550 $c{m}^{-1}$ but none in the 1620-1780 $c{m}^{-1}$ region. It contains only C, H, and O. A 116-mg sample was created with an excess of methylmagnesium bromide, producing 48.7 mL of methane gas collected over mercury at 20°C and 750 mm Hg. The mass spectrum of X has its molecular ion (barely detectable) at 116 m/z and a fragment peak at 98. What does this information tell you about the structure of X?