Exam 13: Nuclear Magnetic Resonance Spectroscopy

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Deduce the identity of the compound whose molecular formula is C4H8O3 from the spectral data provided: IR (cm-1): 2800-3300 (broad), 2950, 1750; 13C NMR (δ): 17.7 (q), 65.4 (q), 72.3 (d), 210.8 (s) (ppm)

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CH3OCH(CH3)CO2H

Deduce the identity of the following compound from the 1H NMR data given. C7H12O4: δ 1.3 (6H, triplet), 3.4 (2H, singlet), 4.2 (4H, quartet) (ppm)

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CH2(CO2CH2CH3)2

In the presence of an external magnetic field the approximate ratio of 1H nuclei with α spins compared to β spins is respectively: ________.

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C

The protons marked Ha and Hb in the molecule below are ________. The protons marked H<sub>a</sub> and H<sub>b</sub> in the molecule below are ________.

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Which of the following functional groups has the most deshielded proton and would be predicted to show an NMR signal that is the farthest downfield?

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Predict the number of signals expected (disregarding splitting) in the 1H spectrum of dibutyl ether.

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Deduce the identity of the following compound from the 1H NMR data given. C3H6Br2: δ 2.4 (2H, quintet), 3.5 (4H, triplet) (ppm)

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A peak split into a doublet of triplets gave the following measurements in its splitting pattern. State the coupling constants (J values) for both the doublet and the triplet. A peak split into a doublet of triplets gave the following measurements in its splitting pattern. State the coupling constants (J values) for both the doublet and the triplet.

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Deduce the identity of the following compound from the 1H NMR data given. C5H12O: δ 1.0 (3H, triplet), 1.2-1.8 (6H, multiplet), 3.0 (1H, broad singlet), 3.8 (2H, triplet) (ppm)

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Predict the number of signals expected, their splitting, and their relative area in the 1H NMR spectrum of 1,2-dichloroethane (ClCH2CH2Cl).

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Calculate the magnetic field that corresponds to the proton resonance frequency of 300.00 MHz. The gyromagnetic ratio of the 1H nucleus is 26,753 s-1 gauss-1.

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Deduce the identity of the following compound from the 1H NMR data given. C6H10O2: δ 2.19 (3H, singlet), 2.70 (2H, singlet) (ppm)

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Predict the number of signals expected (disregarding splitting) in the 1H spectrum of 1,1-dimethylcyclobutane.

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Provide a structure that is consistent with the data below. C7H16O IR (cm-1): 3200-3600 (broad), 2950 1H NMR ( d): 2.9 (1H, broad s), 1.2 (6H, q), 0.9 (9H, t) 13C NMR (d ): 70 (s), 25 (t), 12 (q)

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Predict the number of signals expected in the proton spin decoupled 13C NMR spectrum of the compound shown below. Predict the number of signals expected in the proton spin decoupled <sup>13</sup>C NMR spectrum of the compound shown below.

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Predict the number of signals expected (disregarding splitting) in the 1H NMR spectrum of the compound shown below. Predict the number of signals expected (disregarding splitting) in the <sup>1</sup>H NMR spectrum of the compound shown below.

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Provide a 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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What compound exhibits three singlets in its proton spin decoupled 13C NMR spectrum?

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The following splitting pattern represents one of the vinyl protons of styrene. Identify which proton is represented and list all the coupling constants (J values) for the splitting pattern. The following splitting pattern represents one of the vinyl protons of styrene. Identify which proton is represented and list all the coupling constants (J values) for the splitting pattern.

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How many peaks appear in the proton spin decoupled 13 C NMR spectrum of the compound below? How many peaks appear in the proton spin decoupled <sup>13 </sup>C NMR spectrum of the compound below?

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