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Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether, CH3CH2OCH2CH3?


A) a triplet and a doublet
B) a quartet and a sextet
C) two singlets
D) a triplet and a quartet

E) A) and B)
F) C) and D)

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Predict the splitting of each of the numbered hydrogen atoms in the structure below in a 1H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank to the left of the number. Predict the splitting of each of the numbered hydrogen atoms in the structure below in a <sup>1</sup>H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank to the left of the number.   -______ 1 -______ 1

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Identify the compound (C8H10) that gives the following 1H NMR spectrum. Identify the compound (C<sub>8</sub>H<sub>10</sub>) that gives the following <sup>1</sup>H NMR spectrum.

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o-xylene (1,2-dimethylbenzene)

Identify the compound (C8H10) that gives the following 1H NMR spectrum. Identify the compound (C<sub>8</sub>H<sub>10</sub>) that gives the following <sup>1</sup>H NMR spectrum.

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p-xylene (1,4-dimethylbenzene)

Which C6H12O2 compound gives the following 1H NMR spectrum? Which C<sub>6</sub>H<sub>12</sub>O<sub>2</sub> compound gives the following <sup>1</sup>H NMR spectrum?   A)  1 B)  2 C)  3 D)  4


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

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

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C

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


A) CH3CH(OCH3) 2
B) CH3OCH2CH2CH2CH2OCH3
C) CH3OCH2CH2OCH3
D) CH3OCH2CH(OH) CH3

E) A) and B)
F) A) and C)

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Which of the following is not true regarding 1H NMR spectroscopy?


A) "shielding" leads to peaks at lower values of δ
B) a "downfield" peak appears at a higher value of δ
C) δ for a particular proton depends on the magnetic field strength of the instrument used.
D) on a 300 MHz instrument, a proton that adsorbs irradiation at a frequency 1200 Hz higher than the adsorption of TMS appears at δ 4 ppm.

E) All of the above
F) None of the above

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Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum? \quad\quad\quad\quad\quad\quad O \quad\quad\quad\quad\quad\quad || CH3CH2COCH2CH3\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{3} \quad i \quad\quad\quad ii \quad\quad\quad\quad\quad\quad iii \quad\quad iv


A) i
B) ii
C) iii
D) iv

E) A) and C)
F) None of the above

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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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What is the hydrogen deficiency index for a compound with a molecular formula of C6H6Br2?


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

E) A) and B)
F) A) and C)

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Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet, triplet and quintet?


A) CH3OCH2CH2CH2CH2OH
B) CH3OCH2CH2OCH2CH3
C) CH3OCH2CH2CH2OCH3
D) CH3OCH2CH(CH3) OCH3

E) A) and C)
F) B) and C)

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Which C6H12O2 compound gives the following 1H NMR spectrum? Which C<sub>6</sub>H<sub>12</sub>O<sub>2</sub> compound gives the following <sup>1</sup>H NMR spectrum?   A)  1 B)  2 C)  3 D)  4


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

E) A) and B)
F) B) and C)

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Which C9H10O compound gives the following 1H NMR spectrum? Which C<sub>9</sub>H<sub>10</sub>O compound gives the following <sup>1</sup>H NMR spectrum?   A)  1 B)  2 C)  3 D)  4


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

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

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All of the following compound produce only singlets in a 1H NMR spectrum.  All of the following compound produce only singlets in a <sup>1</sup>H NMR spectrum.      \quad\quad\quad\quad\mathrm{CH}_{3}   \quad\quad\quad\quad\quad |  \mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCCH}_{3}   \quad\quad\quad\quad\quad |  \quad\quad\quad\quad\mathrm{CH}_{3}  All of the following compound produce only singlets in a <sup>1</sup>H NMR spectrum.      \quad\quad\quad\quad\mathrm{CH}_{3}   \quad\quad\quad\quad\quad |  \mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCCH}_{3}   \quad\quad\quad\quad\quad |  \quad\quad\quad\quad\mathrm{CH}_{3} \quad\quad\quad\quadCH3\mathrm{CH}_{3} \quad\quad\quad\quad\quad | CH3CCCCH3\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCCH}_{3} \quad\quad\quad\quad\quad | \quad\quad\quad\quadCH3\mathrm{CH}_{3}

A) True
B) False

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Predict the splitting of each of the numbered hydrogen atoms in the structure below in a 1H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank to the left of the number. Predict the splitting of each of the numbered hydrogen atoms in the structure below in a <sup>1</sup>H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank to the left of the number.   -______ 1 -______ 1

Correct Answer

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What is the hydrogen deficiency index for a compound with a molecular formula of C12H16O?


A) 2
B) 4
C) 5
D) 6

E) A) and B)
F) A) and C)

Correct Answer

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What is the hydrogen deficiency index for a compound with a molecular formula of C6H11N?


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

E) All of the above
F) A) and D)

Correct Answer

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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. -_______

Correct Answer

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Which of the following combinations of peaks appears in the 1H NMR spectrum of 1,2-dimethyoxyethane, CH3OCH2CH2OCH3?


A) two singlets
B) a singlet and a triplet
C) a singlet and two triplets
D) a doublet and a triplet

E) All of the above
F) A) and B)

Correct Answer

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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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