Exam 13: Nuclear Magnetic Resonance Spectroscopy

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Identify the compound (C4H8O) that gives the following 1H NMR spectrum. Identify the compound (C<sub>4</sub>H<sub>8</sub>O) that gives the following <sup>1</sup>H NMR spectrum.

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How many signals appear in proton-decoupled 13C NMR spectrum of 2,5-dimethylhexane?

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Which of the protons in the following molecule appear at the highest ?-value in the 1H NMR spectrum? \quad\quad\quad\quad\quad\quad\quad\quad\quad O \quad\quad\quad\quad\quad\quad\quad\quad\quad || H2C=CH−CH2−C−H\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{C}-\mathrm{H} \quad i \quad\quad\quad ii \quad\quad iii \quad\quad\quad iv

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For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband hydrogen-decoupled 13C NMR spectra. Enter the numerical value in the blank provided to the left of the structure. -_______ For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband hydrogen-decoupled <sup>13</sup>C NMR spectra. Enter the numerical value in the blank provided to the left of the structure. -_______

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Identify the compound (C4H6O2) that gives the following 1H NMR spectrum. Identify the compound (C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>) that gives the following <sup>1</sup>H NMR spectrum.

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Identify the compound (C3H7Cl) that gives the following 1H NMR spectrum. Identify the compound (C<sub>3</sub>H<sub>7</sub>Cl) that gives the following <sup>1</sup>H NMR spectrum.

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The chemical shift of the protons of acetone, CH3COCH3, is 2.1 ppm when the spectrum is obtained at 250 MHz. What is the chemical shift of these protons when the spectrum is acquired at 500 MHz?

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Identify the methyl hydrogen with the highest chemical shift.

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How many signals appear in proton-decoupled 13C NMR spectrum of 3,4-dimethylhexane?

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Which of the carbon atoms in the molecule appears furthest downfield in the 13C NMR spectrum? Which of the carbon atoms in the molecule appears furthest downfield in the <sup>13</sup>C NMR spectrum?

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The coupling constant, J, between the protons of chloroethane is 7 Hz when the spectrum is obtained at 250 MHz. What is the coupling constant between these protons when the spectrum is acquired at 500 MHz?

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What does "Y" denote in the coupling parameter xJy?

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Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet?

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Which C4H9Br compound gives a triplet at approximately 3.5 ppm in the 1H NMR spectrum? Which C<sub>4</sub>H<sub>9</sub>Br compound gives a triplet at approximately 3.5 ppm in the <sup>1</sup>H NMR spectrum?

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How many signals appear in the proton-decoupled 13C NMR spectrum of 4-bromotoluene?

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How many types of equivalent hydrogens are present in the following compound? ​ How many types of equivalent hydrogens are present in the following compound? ​

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How many signals appear in the proton-decoupled 13C NMR spectrum of 1,2-dibromobenzene?

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Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound?

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How many signals appear in the proton-decoupled 13C NMR spectrum of 3-bromotoluene?

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