Exam 13: Structure Determination

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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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D

At what approximate positions might the compound below show IR absorptions? At what approximate positions might the compound below show IR absorptions?

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This compound should show a medium absorption at 2210-2260 cm-1 for the nitrile, and a strong absorption at about 1735 cm-1 for the ester carbonyl.

Which of the following would produce only singlets in an 1H NMR spectrum? Which of the following would produce only singlets in an <sup>1</sup>H NMR spectrum?

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E

Which of the following compounds would have the longest λ\lambda max in the UV region of the electromagnetic spectrum?  Which of the following compounds would have the longest  \lambda <sub>max</sub> in the UV region of the electromagnetic spectrum?

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Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur. -triple bond stretching vibrations.

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Below is the mass spectrum of an unknown hydrocarbon. In addition, this hydrocarbon shows characteristic absorption at 2100 cm - 1 in its IR spectrum. Give the structure of this unknown. Below is the mass spectrum of an unknown hydrocarbon. In addition, this hydrocarbon shows characteristic absorption at 2100 cm <sup>-</sup> <sup>1</sup> in its IR spectrum. Give the structure of this unknown.   (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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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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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 compounds gives an infrared spectrum with peaks at 3300 cm-1 (sharp peak) and 2150 cm-1 (sharp peak)?

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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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Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur. -C=O, C=N, and C=C bond absorptions.

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What is the horizontal axis of a mass spectrum?

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The amount of energy in electromagnetic radiation is related to the frequency and wavelength of the radiation. High energy radiation, like gamma rays, is of:

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

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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 compounds gives an infrared spectrum with peaks at 3300 cm=-=1 (strong, broad peak) and 1640 cm=-=1 (sharp, weak peak)?

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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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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. __________ When looking at an NMR chart the right-hand part of the chart is the __________.

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What is the vertical axis of a mass spectrum?

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Which type of spectroscopy (IR, UV, or MS) will best distinguish between the pair of compounds below? Give a brief reason. Which type of spectroscopy (IR, UV, or MS) will best distinguish between the pair of compounds below? Give a brief reason.

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