Exam 15: Nmr Spectroscopy

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Give the structure of a compound that has a formula of C8H10O2 and has signals in the 13C NMR spectrum at 54.8 ppm (CH3), 63.3 ppm (CH2), 113.6 ppm (CH), 128.3 ppm (CH), 134.11 ppm (C), and 158.6 ppm (C).

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Deduce the identity of the following compound from the spectral data given. C9H10O2: 13C NMR, δ 18.06 (quartet), 45.40 (doublet), 127.32 (doublet), 127.55 (doublet), 128.61 (doublet), 139.70 (singlet), 180.98 (singlet); IR, broad 3500-2800, 1708 cm-1

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Which of the following protons gives an NMR signal with the highest chemical shift value (farthest downfield)? (CH3)2CH-O-CH2CH2CH3 1 2 3 4 5

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Provide the structure that is consistent with the data below. C7H14O2 IR (cm-1): 2950, 1750 1H NMR (d): 2.3 (2H, q), 1.0 (3H, t), 0.9 (9H, s) 13C NMR (d): 185 (s), 78 (s), 29 (t), 14 (q), 12 (q)

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What information does a COSY spectrum give?

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What multiplicities are observed in the spin coupled 13C NMR spectrum of 2,3-dimethyl-2-butene?

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Provide the structure that is consistent with the data below. C5H8Cl2 IR (cm-1): 2950 1H NMR (d): 1.4 (4H, t), 1.2 (4H, t) 13C NMR (d): 62 (s), 26 (t), 23 (t)

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Give the structure of a compound that has a formula of C4H7ClO2 and has a triplet (3H, 1.1 ppm), quintet (2H, 1.2 ppm), triplet (1H, 4.4 ppm), and singlet (1H, 11.6 ppm)in the 1H NMR spectrum.

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How many signals would you expect to see in the 1H NMR spectrum of the following compound? How many signals would you expect to see in the <sup>1</sup>H NMR spectrum of the following compound?

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Give the structure for the compound that has a formula of C10H12O and the following 1H NMR and 13C NMR spectra. Label the hydrogens and the carbons. 1H NMR: 1.2 ppm (t, 3H); 2.3 ppm (s, 3H); 2.6 ppm (q, 2H), 7.2 ppm (d, 2H), and 7.8 ppm (d, 2H). 13C NMR: 7.0 ppm (CH3); 20.9 ppm (CH3); 32.0 ppm (CH2); 128.0 (CH), 129.1 ppm (CH), 134.0 ppm (C); 141.0 ppm(C); and 198.1 ppm (C).

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Deduce the identity of the following compound from the 1H NMR data given. C4H7BrO: δ 2.2 (3H, singlet), 3.5 (2H, triplet), 4.5 (2H, triplet)

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Provide the structure that is consistent with the data below. C5H10O IR (cm-1): 2950 1H NMR (d): 3.5 (4H, s), 0.9 (6H, s) 13C NMR (d): 64 (t), 41 (s), 12 (q)

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How many signals would you expect to see in the 1H NMR spectrum of the following compound? CH3CH2CH2CH3

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Deduce the identity of the compound from the data provided. C5H8O4: IR (cm-1): 2800-3300 (broad), 2950, 1740 13C NMR (δ, splitting): 17.3 (q), 44.3 (s), 210.5 (s)

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Determine the number of signals for 4-methyl-1-propylbenzene in the 1H NMR spectrum.

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Provide the structure that is consistent with the data below. C5H10O2 IR (cm-1): 2950, 1720 1H NMR (δ): 3.6 (s, 3H), 2.5 (septet, 1H), 0.9 (d, 6H) 13C NMR (δ): 190 (s), 55 (q), 40 (d), 16 (q)

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________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned ________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned   in <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. in 1H and 13C NMR spectroscopy.

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Deduce the identity of the compound from the data provided. C10H14O: IR (cm-1): 3200-3500 (broad), 3050, 2950, 1610 1H NMR(δ): 1.0 (s, 6H), 2.0 (s, 3H), 2.8 (broad s, 1H), 7.3 (d, 2H), 7.6 (d, 2H)

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Provide the structure that is consistent with the data below. C5H10O2 IR (cm-1): 3300-2800 (v. broad), 2950, 1710 1H NMR (δ): 12.0 (broad s, 1H), 0.9 (s, 9H) 13C NMR (δ): 220 (s), 45 (s), 12 (q)

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What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens? What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

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