Problem: Deduce the structure of an unknown compound using the following 1H NMR spectrum, mass spectroscopy data, and IR spectrum. 1H NMR spectrum:          Mass Spectrum: δ1.30 (triplet, 6H)                 m/e:      Intensity: (as % of base peak) δ4.29 (quartet, 4H)              222       10% δ 7.4–7.9 (multiplet, 4H)      177        38%                                              149        100%                                             IR Spectrum: Intensity (peak)/Frequency (cm–1):  s / 3100, m / 2900, m / 2800, s / 1740, m-w / 1600, m-w / 1475, m / 1465, m / 1450, m / 1375, s / 1300–1000

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Problem Details

Deduce the structure of an unknown compound using the following 1H NMR spectrum, mass spectroscopy data, and IR spectrum.

1H NMR spectrum:          Mass Spectrum:


δ1.30 (triplet, 6H)                 m/e:      Intensity: (as % of base peak)
δ4.29 (quartet, 4H)              222       10%
δ 7.4–7.9 (multiplet, 4H)      177        38%
                                             149        100%                                            

IR Spectrum:

Intensity (peak)/Frequency (cm–1):  s 3100, m 2900, m 2800, s 1740, m-w 1600, m-w 1475, m 1465, m 1450, m 1375, s 1300–1000

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