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

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H12O which shows no characteristic stretches in the IR between 3600-3300 cm-1,but does around 1600 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>12</sub>O which shows no characteristic stretches in the IR between 3600-3300 cm<sup>-1</sup>,but does around 1600 cm<sup>-1</sup>? Relative integration is shown.

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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?

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C11H14O2? Looking at the 13C-NMR you notice a peak at 174 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>11</sub>H<sub>14</sub>O<sub>2</sub>? Looking at the <sup>13</sup>C-NMR you notice a peak at 174 ppm.Relative integration is shown.

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What is the molecular formula of this compound? m/z Intensity 78 M + \bullet 10)00 79 1 80 3)3 81 0)3

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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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The broadband proton-decoupled 13C NMR spectrum of a hexyl chloride exhibits five signals.Which of these structures could be the correct one for the compound?

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Which form of electromagnetic radiation possesses the least energy?

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How many 13C signals would 1,3-dichlorobenzene give? How many <sup>13</sup>C signals would 1,3-dichlorobenzene give?

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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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In the structure shown,Hb and Hc are classified as: In the structure shown,H<sub>b</sub> and H<sub>c</sub> are classified as:

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H10O2? The 13C-NMR shows characteristic chemical shifts at 22.3,31.1,117.3,157.7,and 171.6 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>6</sub>H<sub>10</sub>O<sub>2</sub>? The <sup>13</sup>C-NMR shows characteristic chemical shifts at 22.3,31.1,117.3,157.7,and 171.6 ppm.Relative integration is shown.

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

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A shielded proton will absorb at a higher frequency (this is the ________ end of the spectrum);and a deshielded proton will absorb at a lower frequency (the _____________ end of the spectrum).

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If all the protons of 1-fluoropentane could be discerned,which would you expect to be at the lowest field in the 1H NMR spectrum of this compound? If all the protons of 1-fluoropentane could be discerned,which would you expect to be at the lowest field in the <sup>1</sup>H NMR spectrum of this compound?

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

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What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C9H18O2 and characteristic 13C-NMR peaks at 11.3,21.6,25.3,49.4,67.1,and 175.5 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>9</sub>H<sub>18</sub>O<sub>2</sub> and characteristic <sup>13</sup>C-NMR peaks at 11.3,21.6,25.3,49.4,67.1,and 175.5 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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The 1H NMR spectrum of which of the compounds below,all of formula C7H12O2,would consist of two 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 two singlets only?

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An organic compound absorbs strongly in the IR at 1687 cm-1.Its 1H NMR spectrum consists of two signals,a singlet at 2.1 ppm and a multiplet centered at 7.1 ppm.Its mass spectrum shows significant peaks at m/z 120,m/z 105 and m/z 77.This information is consistent with which of the following structures? An organic compound absorbs strongly in the IR at 1687 cm<sup>-1</sup>.Its <sup>1</sup>H NMR spectrum consists of two signals,a singlet at 2.1 ppm and a multiplet centered at 7.1 ppm.Its mass spectrum shows significant peaks at m/z 120,m/z 105 and m/z 77.This information is consistent with which of the following structures?

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Which of these compounds will not be represented by a singlet only in the 1H NMR spectrum?

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