Exam 13: Structure Determination

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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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Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene. (CH3)3COHHCl(CH3)3CCl+(CH3)2C=CH2\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { COH } \stackrel { \mathrm { HCl } } { \longrightarrow } \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCl } + \left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { C } = \mathrm { CH } _ { 2 } a) After chromatographic separation, how would you use 1H^1H NMR to help you decide which was which? b) How would the 13C{}^{13}C NMR for the two compounds differ?

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Which of the following does not involve the interaction of molecules with electromagnetic energy?

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The following questions pertain to the charting of NMR spectra.xa0 MATCH a term to each description below.xa0
Refer to instructions. __________ When looking at an NMR chart the right-hand part of the chart is the __________.
TMS
Refer to instructions. __________ The exact place on the chart at which a nucleus absorbs is called its __________.
high-field or upfield side
Refer to instructions. __________ The calibration standard for 1H and 13C NMR is:
MHz
Correct Answer:
Verified
Premises:
Responses:
Refer to instructions. __________ When looking at an NMR chart the right-hand part of the chart is the __________.
TMS
Refer to instructions. __________ The exact place on the chart at which a nucleus absorbs is called its __________.
high-field or upfield side
Refer to instructions. __________ The calibration standard for 1H and 13C NMR is:
MHz
Refer to instructions. __________ The NMR charts are calibrated using an arbitrary scale that is divided into __________ units.
delta d
Refer to instructions. __________ The NMR charts are calibrated using an arbitrary scale that is divided into __________ units.
low-field or downfield side
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Which of the following statements best describes the base peak in a mass spectrum?

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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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What is the horizontal axis of a mass spectrum?

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Instructions: The following questions pertain to the charting of NMR spectra. MATCH a term to each description below. Place the letter of the term in the blank to the left of the description. - Refer to instructions. __________ The exact place on the chart at which a nucleus absorbs is called its __________.

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Nuclear magnetic resonance spectroscopy provides information about a molecule's: a. conjugated pi electron system b. size and formula. c. carbon-hydrogen framework. d. functional groups.

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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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A compound with the molecular formula C5H12O produces only two singlets in the 1H NMR spectrum. a) Propose a structure for this compound. b) How many signals would be present in the 13CNMR^{13}C NMR for this structure?

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Instructions: Select the most reasonable formula for the compounds with the following mass spectral data. Refer to instructions. M+ at m/z = 216

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Instructions: The following questions pertain to the charting of NMR spectra. MATCH a term to each description below. Place the letter of the term in the blank to the left of the description. -Refer to instructions. __________ The calibration standard for 1H and 13C NMR is:

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Cyclohexene and hex-2-yne both have the molecular formula, C6H10. a) How would you use infrared spectroscopy to distinguish between the two compounds b) How could the mass spectrum be used to distinguish between the two compounds?

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Which of the following bonds undergoes stretching at the highest frequency?

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Instructions: The following questions pertain to the charting of NMR spectra. MATCH a term to each description below. Place the letter of the term in the blank to the left of the description. - Refer to instructions. __________ The NMR charts are calibrated using an arbitrary scale that is divided into __________ units.

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Which of the following combinations of peaks appears in the 1H NMR spectrum of 2-methylpropane?

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Instructions: Predict the splitting patterns you would expect for each proton in the molecules below: Predict: Instructions: Predict the splitting patterns you would expect for each proton in the molecules below: Predict:

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Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm-1?

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When 2-bromopropane reacts with ethoxide ion, two products are formed; one is the product of SN2 substitution and the other is the product of E2 elimination. Write the structures of both products, and tell how they could be distinguished using IR spectroscopy.

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