Exam 18: Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

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Which compound would produce the given 1H NMR spectrum below? Which compound would produce the given <sup>1</sup>H NMR spectrum below?    Which compound would produce the given <sup>1</sup>H NMR spectrum below?

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B

Explain how you can use a mass spectrum to determine if a single chlorine is present in a molecule.

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If chlorine is present in a molecule,the M + 2 peak is about one-third the intensity of the M+ peak.

The mass spectrum for an unknown molecule has an M peak with a relative intensity of 50 and an M 1 peak with a relative intensity of 1.65.How many carbons are in the unknown molecule?

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C

Is a chlorine or a bromine present in the molecule responsible for the following mass spectrum? Explain how you know. Is a chlorine or a bromine present in the molecule responsible for the following mass spectrum? Explain how you know.

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Which proton in the following molecule has the greatest chemical shift? Which proton in the following molecule has the greatest chemical shift?

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What is the expected splitting pattern for the indicated hydrogen? What is the expected splitting pattern for the indicated hydrogen?

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For the following molecule,give the splitting patterns for HA,HB,and HC. For the following molecule,give the splitting patterns for H<sub>A</sub>,H<sub>B</sub>,and H<sub>C</sub>.

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How many distinct 13C NMR signals are expected for the following compound? How many distinct <sup>13</sup>C NMR signals are expected for the following compound?

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Give the expected splitting pattern for the indicated hydrogen. Give the expected splitting pattern for the indicated hydrogen.

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Label the base peak and the M peak in the following mass spectrum. Label the base peak and the M<font face=symbol><sup></sup></font> peak in the following mass spectrum.

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What is the expected splitting pattern for the indicated hydrogen? What is the expected splitting pattern for the indicated hydrogen?

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A molecule has the formula C4H9Cl,and its 1H NMR spectrum has only one singlet at 1.49 ppm.Give the structure of this molecule.

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The mass spectrum for an unknown molecule has an M+ peak with a relative intensity of 100 and an M + 1 peak with a relative intensity of 9.905.How many carbons are in the unknown molecule?

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What is the relative ratio of hydrogens in the following molecule? What is the relative ratio of hydrogens in the following molecule?

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How many chemically distinct hydrogen atoms are in the following molecule? How many chemically distinct hydrogen atoms are in the following molecule?

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Which compound would produce the 1H NMR spectrum below? Which compound would produce the <sup>1</sup>H NMR spectrum below?    Which compound would produce the <sup>1</sup>H NMR spectrum below?

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HA splits the 1H NMR signal for HB by 7.4 Hz.By how much does HB split the 1H NMR signal for HA? H<sub>A</sub> splits the <sup>1</sup>H NMR signal for H<sub>B</sub> by 7.4 Hz.By how much does H<sub>B</sub> split the <sup>1</sup>H NMR signal for H<sub>A</sub>?

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Which compound has four distinct signals in its 13C NMR spectrum? Which compound has four distinct signals in its <sup>13</sup>C NMR spectrum?

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Which molecule will have the greatest coupling constant between HA and HB? Which molecule will have the greatest coupling constant between H<sub>A</sub> and H<sub>B</sub>?

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Sketch a predicted 1H NMR spectrum for the following molecule. Sketch a predicted <sup>1</sup>H NMR spectrum for the following molecule.

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