Combined Spectroscopy Problems

On the following pages you will find spectroscopic data for eight different compounds. The data provided will be some combination of Mass Spec (or molecular formula), 1H-NMR, 13C-NMR, and IR spectroscopy information. Use the data provided to determine the structure of each compound. Each problem has only a single compound that completely consistent with the data provided. 1) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 86 (M; 20.2%), m/z = 87 (1.2%) IR:

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H-NMR: 2.40 ppm (triplet; integral = 1.0), 2.13 ppm (singlet; integral = 1.5), 1.60 ppm (sextet; integral = 1.0) and 0.93 ppm (triplet; integral = 1.5).

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C-NMR: 208.93 ppm (singlet), 45.71 ppm (triplet), 29.78 ppm (quartet), 17.41 ppm (triplet), 13.70 ppm (quartet).

2) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 114 (M; 5.2%), m/z = 115 (0.36%) IR:

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H-NMR: 2.71 ppm (singlet; integral = 1.0), 2.19 ppm (singlet; integral = 1.5). C-NMR: 206.87 ppm (singlet), 36.96 ppm (triplet), 29.76 ppm (quartet).

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3) Deduce the structure that corresponds to the spectral data. Molecular Formula: C5H9N IR:

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H-NMR: 2.34 ppm (triplet; integral = 1.0), 1.28-1.82 ppm (multiplet; integral = 2.0), 0.96 ppm (triplet; integral = 1.5). C-NMR: 119.84 ppm (singlet), 27.42 ppm (triplet), 21.86 ppm (triplet), 16.81 ppm (triplet), 13.24 ppm (quartet).

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4) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 136 (M; 75%), m/z = 137 (6.8%) IR:

H-NMR: 9.86 ppm (singlet; integral = 1.0), 7.82 ppm (multiplet; integral = 2.0), 6.98ppm (multiplet; integral = 2.0), 3.86 (singlet; integral = 3.0). C-NMR: 190.70 ppm (doublet), 164.63 ppm (singlet), 131.93 ppm (doublet), 129.97 ppm (singlet), 114.33 ppm (doublet), 55.33 ppm (quartet).

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5) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 136 (M; 75%), m/z = 137 (6.9%) IR:

H-NMR: 12.77 ppm (singlet; integral = 1.0), 7.86 ppm (multiplet; integral = 2.0), 7.31 ppm (multiplet; integral = 2.0), 2.38 (singlet; integral = 3.0). C-NMR: 167.34 ppm (singlet), 142.98 ppm (singlet), 129.37 ppm (doublet), 129.09 ppm (doublet), 128.13 ppm (singlet), 21.10 ppm (quartet).

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6) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 170 (M; 100%), m/z = 171 (13.4%) IR:

H-NMR: 7.22 ppm (multiplet; integral = 2.0), 6.98 ppm (multiplet; integral = 2.0), 6.92 ppm (multiplet; integral = 1.0). C-NMR: 157.21 ppm (singlet), 129.64 ppm (doublet), 123.11 ppm (doublet), 118.81 ppm (doublet).

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7) Deduce the structure that corresponds to the spectral data. Mass Spectrum: m/z = 146 (M; 30.5%), m/z = 147 (2.9%), m/z = 148 (1.4%) Hint: Make sure to consider the M + 2 peak in the mass spectrum, and consider it before the M + 1 peak. IR:

H-NMR: 2.37 ppm (doublet; integral = 2.0), 1.79 ppm (nonet; integral = 1.0), 0.99 ppm (doublet; integral = 6.0). C-NMR: 42.27 ppm (triplet), 28.77 ppm (doublet), 22.09 ppm (quartet).

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8) Deduce the structure that corresponds to the spectral data. Molecular Formula: C11H20O4 IR:

H-NMR: 4.19 ppm (quartet; integral = 2.0), 3.39 ppm (triplet; integral = 1.0), 1.78 ppm (doublet; integral = 2.0), 1.58 ppm (nonet; integral = 1.0), 1.27 ppm (triplet; integral = 3), 0.93 ppm (doublet; integral = 6.0). C-NMR: 169.69 ppm (singlet), 61.22 ppm (triplet), 50.42 ppm (doublet), 37.63 ppm (triplet), 26.27 ppm (doublet), 22.28 ppm (quartet), 14.12 (quartet).

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