An acid-catalyzed reaction was carried out using methyl cellosolve (2-methoxyethanol) as the solvent. When the 2-methoxyethanol was redistilled, a higher-boiling fraction (bp 162 °C) was also recovered. The mass spectrum of this fraction showed the molecular weight to be 134. The IR and NMR spectra are shown here. Determine the structure of this compound, and propose a mechanism for its formation.

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wavelength (um) 5,5 5 8 9 10 2.5 100 3.5 4,5 11 12 13 14 15 16 80 60 40 Problem 14-46 20 4000 3500 3000 2500 2000 1800 1600 1400 1200 1000 800 600 wavenumber (cm-1) 3- TRANSMITTANCE