Exam 15: Nmr Spectroscopy

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Deduce the identity of the following compound from the spectral data given. C7H10O2: 1H NMR, δ 1.16 (3H, singlet), 2.21 (2H, singlet); 13C NMR, δ 216.25 (singlet), 52.57 (singlet), 34.51 (triplet), 20.22 (quartet)

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Deduce the identity of the following compound from the 1H NMR data given. C8H10O: δ 3.4 (3H, singlet), 4.5 (2H, singlet), 7.2 (5H, singlet)

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How many distinct carbon signals are expected in the proton-decoupled 13C NMR spectrum of the compound below? How many distinct carbon signals are expected in the proton-decoupled <sup>13</sup>C NMR spectrum of the compound below?

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Give the splitting pattern for each proton in the 1H NMR spectrum. Give the splitting pattern for each proton in the <sup>1</sup>H NMR spectrum.

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Deduce the identity of the following compound from the spectral data given. C4H8O2: 1H NMR, δ 1.23 (3H, triplet), 2.00 (3H, singlet), 4.02 (2H, quartet); IR, 2980, 1740 cm-1

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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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Provide the structure that is consistent with the data below. C6H10 IR (cm-1): 2950, 2230 1H NMR (d): 2.0 (1H, septet), 1.8 (3H, s), 0.9 (6H, d) 13C NMR (d): 78 (s), 72 (s), 45 (d), 18 (q), 15 (q)

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An unknown compound, C9H12, gave the following NMR spectrum: Triplet at 1.21 ppm (3H)Singlet at 2.30 ppm (3H)Quartet at 2.60 ppm (2H)Singlet at 7.04 ppm (4H) What is the structure of the compound? An unknown compound, C<sub>9</sub>H<sub>12</sub>, gave the following NMR spectrum: Triplet at 1.21 ppm (3H)Singlet at 2.30 ppm (3H)Quartet at 2.60 ppm (2H)Singlet at 7.04 ppm (4H) What is the structure of the compound?

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Which of the following compounds gives the highest chemical shift value (farthest downfield)in the NMR spectrum? Which of the following compounds gives the highest chemical shift value (farthest downfield)in the NMR spectrum?

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Give the integration and splitting pattern for the indicated signals in the 1H NMR spectrum. Give the integration and splitting pattern for the indicated signals in the <sup>1</sup>H NMR spectrum.

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Predict the number of signals expected, their splitting, and their relative area in the 1H NMR spectrum of (CH3)3CCHO.

(Short Answer)
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Predict the integration for each proton in the 1H NMR spectrum. Predict the integration for each proton in the <sup>1</sup>H NMR spectrum.

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Mark with an asterisk each carbon that would not produce a signal in the DEPT 13C NMR spectrum of the compound below. Mark with an asterisk each carbon that would not produce a signal in the DEPT <sup>13</sup>C NMR spectrum of the compound below.

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Which of the following technique(s)can readily distinguish between: Which of the following technique(s)can readily distinguish between:   ? ?

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Deduce the identity of the following compound from the spectral data given. C9H12 : 13C NMR, δ 21.3 (quartet), 127.2 (doublet), 138.0 (singlet)(ppm)

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Which of the following compounds has a triplet at 9.8 in its 1H NMR spectrum? Which of the following compounds has a triplet at 9.8 in its <sup>1</sup>H NMR spectrum?

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Deduce the identity of the following compound from the 1H NMR spectral data given. C9H10O2 : δ 2.2 (3H, singlet), 5.0 (2H, singlet), 7.2 (5H, multilet)(ppm)

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Give the structurre for the compound that has a formula of C11H16O and the following 1H NMR and 13C NMR spectra. Label the hydrogens and the carbons. 1H NMR spectrum: 1.3 ppm, (d, 6H); 3.1 ppm (sept, 1H); 3.2 ppm (s, 3H); 4.6 ppm (s, 2H), 7.1 ppm (d, 2H), 7.1 ppm (d, 2H) 13C NMR spectrum: 24.4 ppm (CH3); 31.7 ppm (CH); 53.5 ppm (CH3); 77.9 ppm (CH2); 126.2 ppm (CH); 127.3 ppm (CH); 134.4 ppm (C); and 147.8 ppm (C).

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The chair form of cyclohexane has protons in two distinct environments, axial and equatorial. When the proton NMR of cyclohexane is run on a 100 MHz instrument at 23°C, only one signal for the compound is observed. Explain this apparent contradiction.

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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?

(Multiple Choice)
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