Exam 9: Nuclear Magnetic Resonance and Mass Spectrometry

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Consider the expected splitting of the C2 proton signal in the 1H NMR spectrum of 2-ethyl-1,3-propanediol.Presuming that the coupling constants for neighboring protons are sufficiently different,and that the instrument has sufficient resolving power,what is the theoretical multiplicity of the C2 proton signal?

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Briefly explain how you might distinguish between the following substances by comparing their 1H-NMR spectra: Briefly explain how you might distinguish between the following substances by comparing their <sup>1</sup>H-NMR spectra:

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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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Consider the expected splitting of signal "b" in the 1H NMR spectrum of 1,1-dichloro-3-methylbutane,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 1,1-dichloro-3-methylbutane,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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A compound with the molecular formula C6H15N gave the following 1H NMR spectrum: triplet, δ\delta 0 0.90 Quartet, δ\delta 2.4 There were no other signals.The most likely structure for the compound is:

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Which form of electromagnetic radiation possesses the least energy?

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

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An acceptable solvent to use for a deuterium exchange experiment with an alcohol would be CDCl3.

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

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

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An unknown compound,F,has the formula C3H6O2.Elucidate the structure of F by scrutinizing its IR,1H NMR and 13C NMR spectra,shown below. An unknown compound,F,has the formula C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>.Elucidate the structure of F by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,F,has the formula C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>.Elucidate the structure of F by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.      An unknown compound,F,has the formula C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>.Elucidate the structure of F by scrutinizing its IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectra,shown below.

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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 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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How many 13C signals would 1,4-dimethylbenzene give? How many <sup>13</sup>C signals would 1,4-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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Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2-phenylbutane. Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2-phenylbutane.

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How many 1H NMR signals would cis-1,2-dichlorocyclopropane give?

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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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