Exam 9: Nuclear Magnetic Resonance and Mass Spectrometry

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C5H11NO,which shows a characteristic stretch in the IR around 1700 cm-1,and a characteristic peak at 202 ppm in the 13C-NMR? 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,which shows a characteristic stretch in the IR around 1700 cm<sup>-1</sup>,and a characteristic peak at 202 ppm in the <sup>13</sup>C-NMR? Relative integration is shown.

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A compound C4H9Br gave the following 1H NMR spectrum: triplet, δ\delta 1.0 (3H); doublet, δ\delta 1.7; multiplet δ\delta 1.8; multiplet, δ\delta 4.1 (1H) Which is a reasonable structure for the compound?

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An unknown compound,I,has the formula C3H7NO2.Elucidate the structure of I by scrutinizing its IR,1H NMR and 13C NMR spectra,shown below. An unknown compound,I,has the formula C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub>.Elucidate the structure of I by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,I,has the formula C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub>.Elucidate the structure of I by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,I,has the formula C<sub>3</sub>H<sub>7</sub>NO<sub>2</sub>.Elucidate the structure of I by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.

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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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In mass spectrometry,the most intense peak is assigned an intensity of 100%,and is referred to as the ___.

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An unknown compound,C,has the formula C7H7Br.Elucidate the structure of C by scrutinizing its IR,1H NMR and 13C NMR spectra,shown below. An unknown compound,C,has the formula C<sub>7</sub>H<sub>7</sub>Br.Elucidate the structure of C by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,C,has the formula C<sub>7</sub>H<sub>7</sub>Br.Elucidate the structure of C by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,C,has the formula C<sub>7</sub>H<sub>7</sub>Br.Elucidate the structure of C by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H10O2? 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>10</sub>O<sub>2</sub>? Relative integration is shown.

(Multiple Choice)
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An unknown compound,E,has the formula C6H12O.Elucidate the structure of E by scrutinizing its IR,1H NMR and 13C NMR spectra,shown below. An unknown compound,E,has the formula C<sub>6</sub>H<sub>12</sub>O.Elucidate the structure of E by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,E,has the formula C<sub>6</sub>H<sub>12</sub>O.Elucidate the structure of E by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,E,has the formula C<sub>6</sub>H<sub>12</sub>O.Elucidate the structure of E by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.

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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.

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

(Multiple Choice)
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A compound with the molecular formula C4H10O gives a 1H NMR spectrum consisting only of a quartet centered at δ\delta 3.5 and a triplet at δ\delta 1.1.The most likely structure for the compound is:

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

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C9H12O? 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>9</sub>H<sub>12</sub>O? Relative integration is shown.

(Multiple Choice)
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Interpret the following 13C/DEPT spectrum of a compound C5H10Br2: elucidate the structure and assign all the 13C resonances. Interpret the following <sup>13</sup>C/DEPT spectrum of a compound C<sub>5</sub>H<sub>10</sub>Br<sub>2</sub>: elucidate the structure and assign all the <sup>13</sup>C resonances.

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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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What compound is used as the standard "zero" reference in both carbon and proton NMR?

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How many 13C signals would you expect from anisole? How many <sup>13</sup>C signals would you expect from anisole?

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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 downfield ( δ\delta 9-10)singlet is observed in the 1H NMR spectrum of:

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Determine the most likely structure of a compound,with the molecular formula C9H12,which gave a 1H NMR spectrum consisting of: a doublet at δ\delta 1.25 A septet at δ\delta 2.90 and A multiplet at δ\delta 7.25  Determine the most likely structure of a compound,with the molecular formula C<sub>9</sub>H<sub>12</sub>,which gave a <sup>1</sup>H NMR spectrum consisting of: a doublet at  \delta  1.25 A septet at  \delta  2.90 and A multiplet at  \delta  7.25   ] ]

(Multiple Choice)
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