Exam 11: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

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Which structure of molecular formula C4H8Cl2 fits the 1H NMR and 13C NMR spectra shown below? Which structure of molecular formula C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub> fits the <sup>1</sup>H NMR and <sup>13</sup>C NMR spectra shown below?     (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) Which structure of molecular formula C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub> fits the <sup>1</sup>H NMR and <sup>13</sup>C NMR spectra shown below?     (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)

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Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet and two signals in the 13C NMR?

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Which feature in the 1H NMR spectrum provides information about the relative numbers of hydrogen atoms of each type found in a compound?

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Instructions: Refer to the structure of 3-methylbutan-2-one below to answer the following question(s). Instructions: Refer to the structure of 3-methylbutan-2-one below to answer the following question(s).    -Refer to instructions.What is the ratio of peak areas upon integration of the spectrum for A,B,and C respectively? -Refer to instructions.What is the ratio of peak areas upon integration of the spectrum for A,B,and C respectively?

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A compound with the molecular formula C6H4ClBr produces only two doublets in the 1H NMR spectrum. a)Propose a structure for this compound. b)How many signals would be present in the 13CNMR for this structure?

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Instructions: Answer the following question(s)for the compound whose 1H NMR spectra is shown below. C4H8O Instructions: Answer the following question(s)for the compound whose <sup>1</sup>H NMR spectra is shown below. C<sub>4</sub>H<sub>8</sub>O   (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/)  -Refer to instructions.Describe each signal in terms of its integration,splitting and chemical shift. (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/) -Refer to instructions.Describe each signal in terms of its integration,splitting and chemical shift.

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Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal,broadband decoupled 13C NMR spectra. -Number of signals:Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal,broadband decoupled <sup>13</sup>C NMR spectra.  -Number of signals:

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Which of the following would not produce nuclear magnetic resonance?

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Instructions: To answer the following questions,consider the data and 1H NMR spectrum below. Instructions: To answer the following questions,consider the data and <sup>1</sup>H NMR spectrum below.    (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/) The mass spectrum of this compound shows a molecular ion at m/z = 113,the IR spectrum has characteristic absorptions at 2270 and 1735 cm<sup>-1</sup>,and the <sup>13</sup>C NMR spectrum has five signals.  -Refer to instructions.Based on the mass spectral data and the IR data,what functional groups are present in this compound? (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/) The mass spectrum of this compound shows a molecular ion at m/z = 113,the IR spectrum has characteristic absorptions at 2270 and 1735 cm-1,and the 13C NMR spectrum has five signals. -Refer to instructions.Based on the mass spectral data and the IR data,what functional groups are present in this compound?

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Instructions: Answer the following question(s)for the compound whose 1H NMR spectra is shown below. C4H8O Instructions: Answer the following question(s)for the compound whose <sup>1</sup>H NMR spectra is shown below. C<sub>4</sub>H<sub>8</sub>O    (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/)  -Refer to instructions.Propose a structure for this compound. (Spectrum obtained from:SDBSWeb:http://www.aist.go.jp/RIODB/SDBS/) -Refer to instructions.Propose a structure for this compound.

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Match a term to each description below. -Match a term to each description below. -

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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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Arrange the following compounds in order of increasing number of signals in a 13C NMR spectrum.Arrange the following compounds in order of increasing number of signals in a <sup>13</sup>C NMR spectrum.

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

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How many positive and negative peaks appear in the DEPT-135 spectrum of 2,4-dimethylpentane?

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Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal,broadband decoupled 13C NMR spectra. -Number of signals:Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal,broadband decoupled <sup>13</sup>C NMR spectra.  -Number of signals:

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Which feature in the 1H NMR spectrum provides information about the electronic environment of the protons in a compound?

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