Exam 9: Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

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Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow? Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

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How many 13C signals would 1,2-dimethylbenzene give? How many <sup>13</sup>C signals would 1,2-dimethylbenzene give?

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C5H11NO? In the 13C-NMR spectrum you notice that the farthest peak downfield has a chemical shift of 173 ppm.Relative integration is shown. What is the structure of the compound in the following <sup>1</sup>H-NMR spectrum with the molecular formula C<sub>5</sub>H<sub>11</sub>NO? In the <sup>13</sup>C-NMR spectrum you notice that the farthest peak downfield has a chemical shift of 173 ppm.Relative integration is shown.

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Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow? Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

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A mass spectrometer sorts ions on the basis of their _______________.

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In electron impact mass spectrometry,a beam of high-energy electrons initially dislodges one electron from the compound being studied.This produces a positively charged ion called the ____________________.

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C8H14? Relative integration is shown. What is the structure of the compound in the following <sup>1</sup>H-NMR spectrum with the molecular formula C<sub>8</sub>H<sub>14</sub>? Relative integration is shown.

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Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow? Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

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A compound with the molecular formula C8H9ClO gave the following 1H NMR spectrum: triplet, δ\delta 3.7 Triplet, δ\delta 4.2 Multiplet δ\delta 7.1 There was no evidence of an -OH band in the IR spectrum.The most likely structure for the compound is:  A compound with the molecular formula C<sub>8</sub>H<sub>9</sub>ClO gave the following <sup>1</sup>H NMR spectrum: triplet, \delta  3.7 Triplet, \delta  4.2 Multiplet \delta   7.1 There was no evidence of an -OH band in the IR spectrum.The most likely structure for the compound is:

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A compound with the molecular formula C8H9BrO gave the following 1H NMR spectrum: triplet, δ\delta 1.4 Quartet, δ\delta 3.9 Multiplet, δ\delta 7.0 (4H) There was no evidence of an -OH band in the IR spectrum.A possible structure for the compound is:  A compound with the molecular formula C<sub>8</sub>H<sub>9</sub>BrO gave the following <sup>1</sup>H NMR spectrum: triplet, \delta   1.4 Quartet, \delta   3.9 Multiplet, \delta   7.0 (4H) There was no evidence of an -OH band in the IR spectrum.A possible structure for the compound is:

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C10H11N? Looking at the 13C-NMR you notice 10 distinct peaks,and the IR has a characteristic peak around 2250 cm-1.Relative integration is shown. What is the structure of the compound in the following <sup>1</sup>H-NMR spectrum with the molecular formula C<sub>10</sub>H<sub>11</sub>N? Looking at the <sup>13</sup>C-NMR you notice 10 distinct peaks,and the IR has a characteristic peak around 2250 cm<sup>-1</sup>.Relative integration is shown.

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The 1H NMR spectrum of which of these compounds would consist of a triplet,singlet and quartet only?

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Predict the splitting pattern you would observe for the proton at C3 of 2,3-dimethyl-2-phenylbutane. Predict the splitting pattern you would observe for the proton at C3 of 2,3-dimethyl-2-phenylbutane.

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A compound C5H10O gave the following spectral data: 1H NMR spectrum IR spectrum Doublet, δ\delta 1.10 strong peak Singlet, δ\delta 2.10 near 1720 cm-1 Septet, δ\delta 2.50 Which is a reasonable structure for the compound?  A compound C<sub>5</sub>H<sub>10</sub>O gave the following spectral data: <sup>1</sup>H NMR spectrum IR spectrum Doublet, \delta   1.10 strong peak Singlet, \delta   2.10 near 1720 cm<sup>-1</sup> Septet, \delta   2.50 Which is a reasonable structure for the compound?

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A compound with the molecular formula C10H13Cl gave the following 1H NMR spectrum: singlet, δ\delta 1.6 Singlet, δ\delta 3.1 Multiplet, δ\delta 7.2 (5H) The most likely structure for the compound is:  A compound with the molecular formula C<sub>10</sub>H<sub>13</sub>Cl gave the following <sup>1</sup>H NMR spectrum: singlet, \delta   1.6 Singlet, \delta   3.1 Multiplet, \delta   7.2 (5H) The most likely structure for the compound is:

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What is the nitrogen rule?

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C10H12O2? Relative integration is shown. What is the structure of the compound in the following <sup>1</sup>H-NMR spectrum with the molecular formula C<sub>10</sub>H<sub>12</sub>O<sub>2</sub>? Relative integration is shown.

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How many signals will be recorded in the broadband proton-decoupled 13C spectrum of 4-chloro-1-ethylbenzene? How many signals will be recorded in the broadband proton-decoupled <sup>13</sup>C spectrum of 4-chloro-1-ethylbenzene?

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Consider the expected splitting of signal "b" in the 1H NMR spectrum of 1-methoxy-2-methylpropane,shown below.Presuming that Jab is sufficiently different from Jbc and that the instrument has sufficient resolving power,what is the theoretical multiplicity of signal "b"? Consider the expected splitting of signal b in the <sup>1</sup>H NMR spectrum of 1-methoxy-2-methylpropane,shown below.Presuming that J<sub>ab</sub> is sufficiently different from J<sub>bc</sub> and that the instrument has sufficient resolving power,what is the theoretical multiplicity of signal b?

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What can be determined from the relative abundance of the M + \bullet +1 peak?

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