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Which of the following compounds gives a 1H NMR spectrum consisting of only two singlets?


A) CH3OCH2CH2OCH2CH3
B) CH3OCH2CH2CH2CH2OH
C) CH3OC(CH3) 2OCH3
D) CH3OCH2CH(CH3) OCH3

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

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C

Examining the infrared spectrum of a compound allows us to:


A) determine the types of functional groups present in the compound
B) determine the carbon-hydrogen framework of the compound
C) determine the molecular weight of the compound
D) determine the nature of the conjugated pi electron system in the compound

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

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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 peaks at 3300 cm-1 (strong, broad peak) and 1640 cm-1 (sharp, weak peak) ?


A) Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (strong, broad peak)  and 1640 cm<sup>-1</sup> (sharp, weak peak) ? A)    B)    C)    D)
B) Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (strong, broad peak)  and 1640 cm<sup>-1</sup> (sharp, weak peak) ? A)    B)    C)    D)
C) Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (strong, broad peak)  and 1640 cm<sup>-1</sup> (sharp, weak peak) ? A)    B)    C)    D)
D) Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (strong, broad peak)  and 1640 cm<sup>-1</sup> (sharp, weak peak) ? A)    B)    C)    D)

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

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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?


A) number of signals
B) integration of signals
C) splitting of signals
D) chemical shift

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

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


A) number of signals
B) integration of signals
C) splitting of signals
D) chemical shift

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

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D

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.


A) TMS
B) high-field or upfield side
C) MHz
D) delta d
E) low-field or downfield side
F) chemical shift
G) specific absorption

H) C) and G)
I) F) and G)

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

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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 __________.


A) TMS
B) high-field or upfield side
C) MHz
D) delta d
E) low-field or downfield side
F) chemical shift
G) specific absorption

H) All of the above
I) B) and F)

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Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s). Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s).   (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) Refer to instructions. What peak represents M<sup>+</sup>? (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) Refer to instructions. What peak represents M+?

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The peak a...

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


A) C=O
B) C-O
C) C=C
D) C-C

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

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A

The amount of energy in infrared light corresponds to:


A) the amount of energy needed to promote one electron from a bonding to an antibonding molecular orbital
B) the amount of energy needed to fragment a molecule
C) the amount of energy needed to strip a molecule of one electron to generate a cation radical
D) the amount of energy needed to increase certain molecular motions, such as bond vibrations, in organic molecules

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

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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?   A)  A B)  B C)  C D)  D E)  all of these produce only singlets


A) A
B) B
C) C
D) D
E) all of these produce only singlets

F) A) and B)
G) None of the above

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When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to: a. the amount necessary to increase molecular motions in functional groups b. the amount necessary to excite electrons from one molecular orbital to another c. the amount necessary to "flip" the spin of atomic nuclei d. the amount necessary to strip a molecule of one electron to generate a radical cation

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Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the highest energy?


A) radio waves
B) ultraviolet
C) infrared
D) visible

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

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Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s). Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s).   (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) Refer to instructions. What peak represents the base peak? (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) Refer to instructions. What peak represents the base peak?

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The peak a...

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Assume you are carrying out the conversion of 1-bromobutane to butan-1-ol. How could you use IR spectroscopy to determine when the reaction is complete? Assume you are carrying out the conversion of 1-bromobutane to butan-1-ol. How could you use IR spectroscopy to determine when the reaction is complete?

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The infrared spectrum of the starting br...

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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) ?


A) CH3CH2CCH\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { C } \equiv \mathrm { CH }
B) CH3CCCH3\mathrm { CH } _ { 3 } \mathrm { C } \equiv \mathrm { CCH } _ { 3 }
C)  Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (sharp peak)  and 2150 cm<sup>-1</sup> (sharp peak) ? A)   \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { C } \equiv \mathrm { CH }  B)   \mathrm { CH } _ { 3 } \mathrm { C } \equiv \mathrm { CCH } _ { 3 }  C)    D)
D)  Which of the following compounds gives an infrared spectrum with peaks at 3300 cm<sup>-1</sup> (sharp peak)  and 2150 cm<sup>-1</sup> (sharp peak) ? A)   \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { C } \equiv \mathrm { CH }  B)   \mathrm { CH } _ { 3 } \mathrm { C } \equiv \mathrm { CCH } _ { 3 }  C)    D)

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

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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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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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The signals at 1.05 and 2.45 d are chara...

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