Exam 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

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Exhibit 13-1 The following question(s) pertain to the charting of NMR spectra.MATCH a term to each description below. -_____ The NMR charts are calibrated using an arbitrary scale that is divided into _____ units.

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Explain why all protons in a molecule do not absorb rf energy at the same frequency.

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Exhibit 13-11 Answer the question(s) for the compound whose 1H NMR spectra is shown below. C5H12O Exhibit 13-11 Answer the question(s) for the compound whose <sup>1</sup>H NMR spectra is shown below. C<sub>5</sub>H<sub>12</sub>O   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-11.Propose a structure for this compound. Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-11.Propose a structure for this compound.

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Exhibit 13-11 Answer the question(s) for the compound whose 1H NMR spectra is shown below. C5H12O Exhibit 13-11 Answer the question(s) for the compound whose <sup>1</sup>H NMR spectra is shown below. C<sub>5</sub>H<sub>12</sub>O   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-11.Describe each signal in the <sup>1</sup>H NMR in terms of its integration,splitting and chemical shift. Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-11.Describe each signal in the 1H NMR in terms of its integration,splitting and chemical shift.

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For a nucleus to exhibit the nuclear magnetic resonance phenomenon,it must be magnetic.Magnetic nuclei include:

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​Propose a structure for an alkyl halide,C4H9Br,that has the following 13C NMR data: Broadband decoupled 13C NMR: 18.3,38.6,60.2 δ DEPT-90: 38.6 δ DEPT-135: positive peak at 18.3,60.2 δ;negative peak at 38.6 δ

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Exhibit 13-12 Answer the question(s) for the compound whose 1H NMR spectra is shown below. C8H7ClO Exhibit 13-12 Answer the question(s) for the compound whose <sup>1</sup>H NMR spectra is shown below. C<sub>8</sub>H<sub>7</sub>ClO   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-12.Describe the signal at 2.6 δ in terms of integration,splitting and chemical shift. Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-12.Describe the signal at 2.6 δ in terms of integration,splitting and chemical shift.

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How would you use 1H and 13C NMR to help you distinguish between these two isomeric structures? How would you use <sup>1</sup>H and <sup>13</sup>C NMR to help you distinguish between these two isomeric structures?

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Identify the two numbered hydrogen atoms as: Identify the two numbered hydrogen atoms as:

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Exhibit 13-9 To answer the following question(s),consider the data and 1H NMR spectrum below: 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. Exhibit 13-9 To answer the following question(s),consider the data and <sup>1</sup>H NMR spectrum below: 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.   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-9.Describe the signals at 4.35 δ and 1.3 δ in terms of their integration,splitting and chemical shift. Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-9.Describe the signals at 4.35 δ and 1.3 δ in terms of their integration,splitting and chemical shift.

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Which structure of molecular formula C4H8Cl2 fits both the 1H NMR and 13C NMR spectra shown below?

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​What would be the approximate positions at which you would expect 2-chloro-3-butyne to show 13C NMR absorptions? ​What would be the approximate positions at which you would expect 2-chloro-3-butyne to show <sup>13</sup>C NMR absorptions?

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​The molecular formula of a certain compound is C4H9OBr.It has the following 1H NMR data: 1.30 δ (6H,singlet),3.94 δ (2H,doublet),and 2.51 δ (1H,triplet).Propose a structure for the compound using the information given.

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Exhibit 13-9 To answer the following question(s),consider the data and 1H NMR spectrum below: 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. Exhibit 13-9 To answer the following question(s),consider the data and <sup>1</sup>H NMR spectrum below: 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.   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-9.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/ -Refer to Exhibit 13-9.Based on the mass spectral data and the IR data,what functional groups are present in this compound?

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Describe how you could differentiate the following compounds using a DEPT NMR experiment. Describe how you could differentiate the following compounds using a DEPT NMR experiment.

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Exhibit 13-9 To answer the following question(s),consider the data and 1H NMR spectrum below: 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. Exhibit 13-9 To answer the following question(s),consider the data and <sup>1</sup>H NMR spectrum below: 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.   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-9.Describe the signal at 3.5 δ in terms of its integration,splitting pattern and chemical shift. Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 13-9.Describe the signal at 3.5 δ in terms of its integration,splitting pattern and chemical shift.

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How many signals would appear in the proton NMR for the following substance? Atoms other than carbon and hydrogen are labeled. How many signals would appear in the proton NMR for the following substance? Atoms other than carbon and hydrogen are labeled.

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Propose a structure for a compound,C6H14O,with the following 13C NMR spectral data: Broadband decoupled 13C NMR: 23.0,68.4 δ DEPT-90: 68.4 δ DEPT-135: positive peaks at 23.0,68.4 δ;no negative peaks

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Consider the following structure.Atoms other than carbon and hydrogen are labeled.The carbon atoms are designated by numbers. Consider the following structure.Atoms other than carbon and hydrogen are labeled.The carbon atoms are designated by numbers.   Which carbon atom(s) will produce a signal in a DEPT-90 spectrum? Which carbon atom(s) will produce a signal in a DEPT-90 spectrum?

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Exhibit 13-1 The following question(s) pertain to the charting of NMR spectra.MATCH a term to each description below. -_____ When looking at an NMR chart the right-hand part of the chart is the _____.

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