Question

Use the spectral data provided to determine the structure of the unknown compound.

The following compound is a neutral, volatile liquid (boiling point 90^oC). The Mass, IR, and ¹H NMR spectra, along with ¹³C NMR data, are given below.

Elemental Analysis:

C 58.80

H 9.87

O 31.33

H NMR Mass Spectr 43 59 102 30 40 50 60 70 00 90 100 110 20 130 140 50 160 70 150 190 200 m/e Infrared Spectrum Wave Number, cm /00 4000 3000 2500 2000 500 300 1200 1100 000 900 B00 Wavelength, microns ppm, C Spectral Data: singlet, 174.5 ppm quartet, 50.7 ppm doublet, 35.2 ppm quartet, 18.5 ppm