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Predict the chemical shifts for the signals in the 1H NMR spectrum for the following compound. Predict the chemical shifts for the signals in the <sup>1</sup>H NMR spectrum for the following compound.

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How many signals would you expect in the 1H NMR spectrum of the following compound? How many signals would you expect in the <sup>1</sup>H NMR spectrum of the following compound?

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How many signals would you expect in the 1H NMR spectrum of CH3OCH2CH2OCH3?


A) 1
B) 2
C) 3
D) 4
E) 5

F) A) and D)
G) A) and C)

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Propose a structure for a compound, with molecular formula C6H10O, that fits the following spectroscopic data: IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1 1H NMR: 1.0 δ\delta (triplet, 3H), 1.5 δ\delta (singlet, 3H), 1.6 δ\delta (quartet, 2H), 2.0 δ\delta (singlet, 1H), 2.5 δ\delta (singlet, 1H) 13C NMR: 4.1, 26, 35, 67.6, 69.4

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11ea894b_ad07_2367_bba7_017f82bda289_TB4454_00_TB4454_00

Predict the multiplicity of each signal in the expected 1H NMR spectrum of 2,3-dimethyl-2-pentanol.

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A compound with molecular formula C8H10O has the following 1H NMR spectrum. Which of the following is the correct number of protons giving rise to each signal. A compound with molecular formula C<sub>8</sub>H<sub>10</sub>O has the following <sup>1</sup>H NMR spectrum. Which of the following is the correct number of protons giving rise to each signal.

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I – 3H, II...

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Which of the following compounds will display a singlet, a triplet and a quartet in its 1H NMR spectrum?


A) 2-chloro-4-methylpentane
B) 3-chloro-2-methylpentane
C) 3-chloropentane
D) 1-chloro-2,2-dimethylbutane
E) 3-chloro-3-methylpentane

F) A) and C)
G) C) and D)

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Which of the following displays a signal in the DEPT-90 13C NMR spectroscopy?


A) CH3
B) CH2
C) CH
D) C
E) none of these

F) C) and D)
G) A) and D)

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A compound with molecular formula C10H14 displays the following IR, 1H NMR, 13C NMR spectra. Propose a structure for this compound. A compound with molecular formula C<sub>10</sub>H<sub>14</sub> displays the following IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR spectra. Propose a structure for this compound.        SDBS A compound with molecular formula C<sub>10</sub>H<sub>14</sub> displays the following IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR spectra. Propose a structure for this compound.        SDBS A compound with molecular formula C<sub>10</sub>H<sub>14</sub> displays the following IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR spectra. Propose a structure for this compound.        SDBS SDBS

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How many signals would you expect to find in the 13C NMR spectrum of the following compound? How many signals would you expect to find in the <sup>13</sup>C NMR spectrum of the following compound?   A)  6 B)  7 C)  8 D)  9 E)  10


A) 6
B) 7
C) 8
D) 9
E) 10

F) B) and D)
G) C) and D)

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B

Which of the following is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound? Which of the following is the best prediction of the chemical shifts for the signals in the <sup>1</sup>H NMR spectrum for the following compound?   A)  I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm B)  I = 3.4 ppm, II = 2.2 ppm, III = 2.2 ppm, IV = 3.4 ppm C)  I = 3.4 ppm, II = 2.2 ppm, III = 4.2 ppm, IV = 3.4 ppm D)  I = 3.4 ppm, II = 4.2 ppm, III = 4.2 ppm, IV = 3.4 ppm E)  none of these


A) I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm
B) I = 3.4 ppm, II = 2.2 ppm, III = 2.2 ppm, IV = 3.4 ppm
C) I = 3.4 ppm, II = 2.2 ppm, III = 4.2 ppm, IV = 3.4 ppm
D) I = 3.4 ppm, II = 4.2 ppm, III = 4.2 ppm, IV = 3.4 ppm
E) none of these

F) None of the above
G) D) and E)

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A compound with a molecular formula of C8H16O has the following 1H NMR spectrum. Provide a structure that is consistent with this spectrum. SHAPE \* MERGEFORMAT A compound with a molecular formula of C<sub>8</sub>H<sub>16</sub>O has the following <sup>1</sup>H NMR spectrum. Provide a structure that is consistent with this spectrum. SHAPE \* MERGEFORMAT    A compound with a molecular formula of C<sub>8</sub>H<sub>16</sub>O has the following <sup>1</sup>H NMR spectrum. Provide a structure that is consistent with this spectrum. SHAPE \* MERGEFORMAT

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Which of the following compounds will display only two singlets in its 1H NMR spectrum? Which of the following compounds will display only two singlets in its <sup>1</sup>H NMR spectrum?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

F) C) and D)
G) None of the above

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Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound. Determine the multiplicity of each signal in the expected <sup>1</sup>H NMR spectrum of the following compound.

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How many 1H NMR signals does 2-chloro-3-methyl-2-butene exhibit?


A) 1
B) 2
C) 3
D) 4
E) 5

F) D) and E)
G) A) and B)

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Which of the following does not display a signal in the DEPT-135 13C NMR spectroscopy?


A) CH3
B) CH2
C) CH
D) C
E) none of these

F) C) and D)
G) A) and B)

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Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound. Determine the multiplicity of each signal in the expected <sup>1</sup>H NMR spectrum of the following compound.

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How many signals would you expect in the 1H NMR spectrum of the following compound? How many signals would you expect in the <sup>1</sup>H NMR spectrum of the following compound?

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3

A compound with a molecular formula C8H15ClO3 has the following 1H NMR spectrum. The IR spectrum shows a strong absorption at 1800 cm-1. Which of the following structures is consistent with this spectrum? A compound with a molecular formula C<sub>8</sub>H<sub>15</sub>ClO<sub>3</sub> has the following <sup>1</sup>H NMR spectrum. The IR spectrum shows a strong absorption at 1800 cm<sup>-1</sup>. Which of the following structures is consistent with this spectrum?     A)  I B)  II C)  III D)  IV E)  none of these A compound with a molecular formula C<sub>8</sub>H<sub>15</sub>ClO<sub>3</sub> has the following <sup>1</sup>H NMR spectrum. The IR spectrum shows a strong absorption at 1800 cm<sup>-1</sup>. Which of the following structures is consistent with this spectrum?     A)  I B)  II C)  III D)  IV E)  none of these


A) I
B) II
C) III
D) IV
E) none of these

F) B) and E)
G) C) and D)

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Draw a structure, with a formula of C4H9Br, which has an integration of 3H, 2H, 2H, and 2H.

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