Exam 9: Nuclear Magnetic Resonance and Mass Spectrometry

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An unknown compound,V,has the formula C8H10O.Elucidate the structure of V by scrutinizing its IR,1H NMR and 13C NMR spectra,shown below. An unknown compound,V,has the formula C<sub>8</sub>H<sub>10</sub>O.Elucidate the structure of V by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,V,has the formula C<sub>8</sub>H<sub>10</sub>O.Elucidate the structure of V by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,V,has the formula C<sub>8</sub>H<sub>10</sub>O.Elucidate the structure of V by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.

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

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The mass spectra of alkyl bromides and chlorides are characterized by an unusually intense ___.

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Which proton(s)of the compound below would appear as a triplet in the 1H NMR spectrum? Which proton(s)of the compound below would appear as a triplet in the <sup>1</sup>H NMR spectrum?

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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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What is the molecular formula of this compound? m/z intensity 84 M+ ∙\bullet 10.00 85 0.56 86 0.04

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Determine the likely structure for a compound A (C6H10O),which is found to decolorize bromine in carbon tetrachloride.Its spectral data is as follows: 1H NMR IR Triplet, δ\delta 1.0 singlet, δ\delta 2.4 2200 cm-1 (sharp) Singlet, δ\delta 1.4 singlet, δ\delta 3.4 3300 cm-1 (sharp) Quartet, δ\delta 1.6 3500 cm-1 (broad)  Determine the likely structure for a compound A (C<sub>6</sub>H<sub>10</sub>O),which is found to decolorize bromine in carbon tetrachloride.Its spectral data is as follows: <sup>1</sup>H NMR IR Triplet, \delta 1.0 singlet, \delta 2.4 2200 cm<sup>-1</sup> (sharp) Singlet, \delta  1.4 singlet, \delta 3.4 3300 cm<sup>-1 </sup>(sharp) Quartet, \delta  1.6 3500 cm<sup>-1 </sup>(broad)

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Which proton(s)of the compound below would appear as a doublet in the 1H NMR spectrum? Which proton(s)of the compound below would appear as a doublet in the <sup>1</sup>H NMR spectrum?

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Select the structure of a compound C6H14 with a base peak at m/z 43.

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C4H8O? 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>4</sub>H<sub>8</sub>O? Relative integration is shown.

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When measuring the integral for a particular peak in the NMR spectrum,we are not interested in the peak height as much as in the ___.

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The 1H NMR spectrum of which of the compounds below,all of formula C7H12O2,would consist of three singlets only? The <sup>1</sup>H NMR spectrum of which of the compounds below,all of formula C<sub>7</sub>H<sub>12</sub>O<sub>2</sub>,would consist of three singlets only?

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

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The 1H NMR spectrum of which of the compounds below,all of formula C7H12O2,would consist of a singlet,a doublet and a triplet only? The <sup>1</sup>H NMR spectrum of which of the compounds below,all of formula C<sub>7</sub>H<sub>12</sub>O<sub>2</sub>,would consist of a singlet,a doublet and a triplet only?

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The C7 compound which gives 3 signals in the broadband proton-decoupled 13C spectrum could be:

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C12H17NO and a characteristic IR stretch near 1700 cm-1 and a characteristic peak in the 13C-NMR at 170 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>12</sub>H<sub>17</sub>NO and a characteristic IR stretch near 1700 cm<sup>-1</sup> and a characteristic peak in the <sup>13</sup>C-NMR at 170 ppm? Relative integration is shown.

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C9H14O? IR data shows no characteristic peak around 1700 cm-1.The 13C-NMR chemical shifts (ppm): 108.4,50.9,31.6,23.5,2.0.Relative integration is known. What is the structure of the compound in the following <sup>1</sup>H-NMR spectrum with the molecular formula C<sub>9</sub>H<sub>14</sub>O? IR data shows no characteristic peak around 1700 cm<sup>-1</sup>.The <sup>13</sup>C-NMR chemical shifts (ppm): 108.4,50.9,31.6,23.5,2.0.Relative integration is known.

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C5H8O? The IR spectrum does show a characteristic stretch around 1700 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>5</sub>H<sub>8</sub>O? The IR spectrum does show a characteristic stretch around 1700 cm<sup>-1</sup>.Relative integration is shown.

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For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H11N? In the IR spectrum you notice a stretch at about 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>6</sub>H<sub>11</sub>N? In the IR spectrum you notice a stretch at about 2250 cm<sup>-1</sup>.Relative integration is shown.

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