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What type(s) of molecular motion is (are) observed using infrared spectroscopy?


A) Stretching and bending
B) Rotation and excitation
C) Spin flipping
D) Fragmentation

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

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Compared to a C-H bond,a C-D bond will vibrate where in the infrared spectrum?


A) Higher molecular weight
B) Lower molecular weight
C) Lower wavenumbers
D) Higher wavenumbers

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

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Which of the following statements is (are) true about a compound that has molecular ion peaks in its mass spectrum at mass 170 and 172 and shows prominent peaks in its IR spectrum at 3150-3000 and 1600 cm-1?


A) The compound is not pure.
B) The compound contains a halogen.
C) The compound contains an OH group and Csp3-H hybridized bonds.
D) Both (The compound is not pure) and (The compound contains a halogen) are true statements.
E) Both (The compound is not pure) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements.

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

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An IR spectrum has the following potentially important absorptions: 3091,3067,2963,2921,2252,1603,1499,1455,1416,1078,1031,941,735,and 696 cm-1.Indicate which structure corresponds to the IR data. An IR spectrum has the following potentially important absorptions: 3091,3067,2963,2921,2252,1603,1499,1455,1416,1078,1031,941,735,and 696 cm<sup>-1</sup>.Indicate which structure corresponds to the IR data.   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

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Examine the IR below and classify the compound. Examine the IR below and classify the compound.   A) Alcohol B) Arene C) Amine D) Ketone E) Carbocylic acid


A) Alcohol
B) Arene
C) Amine
D) Ketone
E) Carbocylic acid

F) A) and C)
G) B) and D)

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Which of the indicated C-H bonds absorbs at the lowest wave number in the IR spectrum? Which of the indicated C-H bonds absorbs at the lowest wave number in the IR spectrum?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

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Consider the three organic compounds drawn below.Which of the following statements is (are) true about the IR spectra of I,II,and III? Consider the three organic compounds drawn below.Which of the following statements is (are) true about the IR spectra of I,II,and III?   A) I shows strong absorptions at 2950 cm<sup>-1</sup> and 1700 cm<sup>-1</sup>. B) II shows strong absorptions at 2950 cm<sup>-1</sup> and 2250 cm<sup>-1</sup>. C) III shows strong absorptions at 2950 cm<sup>-1</sup> and 3200-3600 cm<sup>-1</sup>. D) Statements (I shows strong absorptions at 2950 cm<sup>-1</sup> and 1700 cm<sup>-1</sup>) and (III shows strong absorptions at 2950 cm<sup>-1</sup> and 3200-3600 cm<sup>-1</sup>) are true.


A) I shows strong absorptions at 2950 cm-1 and 1700 cm-1.
B) II shows strong absorptions at 2950 cm-1 and 2250 cm-1.
C) III shows strong absorptions at 2950 cm-1 and 3200-3600 cm-1.
D) Statements (I shows strong absorptions at 2950 cm-1 and 1700 cm-1) and (III shows strong absorptions at 2950 cm-1 and 3200-3600 cm-1) are true.

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

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13C NMR is a technique in which the total number of signals represents the number of unique carbon atoms in a molecule.Propose a structure that is consistent with the following data. a.The IR includes peaks at 1603 and 1495 cm-1. b.The 13C NMR has a total of 7 signals. c.The compound has one acidic proton. <sup>13</sup>C NMR is a technique in which the total number of signals represents the number of unique carbon atoms in a molecule.Propose a structure that is consistent with the following data. a.The IR includes peaks at 1603 and 1495 cm<sup>-1</sup>. b.The <sup>13</sup>C NMR has a total of 7 signals. c.The compound has one acidic proton.   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) A) and D)
F) A) and C)

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Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 104 and shows prominent peaks in its IR spectrum at 3200-2850 cm-1?


A) The compound has a molecular mass of 104.
B) The compound contains a C=O group and Csp3-H hybridized bonds.
C) The compound contains an OH group and Csp3-H hybridized bonds.
D) Both (The compound has a molecular mass of 104) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements.
E) Both (The compound has a molecular mass of 104) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements.

F) D) and E)
G) B) and E)

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Which of the following information is primarily obtained from an IR spectrum?


A) Conjugated p system present in a compound.
B) Functional groups present in a compound.
C) Molecular weight of a compound.
D) The carbon and hydrogen framework of a compound.

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

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Examine the IR below and classify the compound. Examine the IR below and classify the compound.   A) Alcohol B) Aldehyde C) Carboxylic acid D) Ketone


A) Alcohol
B) Aldehyde
C) Carboxylic acid
D) Ketone

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

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Why is the infrared absorption for the stretching motion of internal alkynes rarely observed?


A) They do not form cations.
B) They are too strong.
C) Stretching in internal alkynes does not involve a change in dipole moment.
D) They do not have hydrogens.

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

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What type of signal(s) would you observe in the mass and/or infrared spectrum of the following compound? What type of signal(s) would you observe in the mass and/or infrared spectrum of the following compound?   A) A signal at 96 amu B) Two signals at 112 and 114 amu C) A signal at 1600 cm<sup>-1</sup> D) A signal at 1720 cm<sup>-1</sup>


A) A signal at 96 amu
B) Two signals at 112 and 114 amu
C) A signal at 1600 cm-1
D) A signal at 1720 cm-1

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

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Which of the following statements is (are) accurate about the IR spectrum of compounds I,II,and III below? Which of the following statements is (are) accurate about the IR spectrum of compounds I,II,and III below?   A) Compound I shows absorptions at 2950 and 1700 cm<sup>-1</sup>. B) Compound II shows absorptions at 3200-3600 and 1650 cm<sup>-1</sup>. C) Compound III shows absorptions at 3200-3600 and 2950 cm<sup>-1</sup>. D) Both (Compound I shows absorptions at 2950 and 1700 cm<sup>-1</sup>) and (Compound II shows absorptions at 3200-3600 and 1650 cm<sup>-1</sup>) are true.


A) Compound I shows absorptions at 2950 and 1700 cm-1.
B) Compound II shows absorptions at 3200-3600 and 1650 cm-1.
C) Compound III shows absorptions at 3200-3600 and 2950 cm-1.
D) Both (Compound I shows absorptions at 2950 and 1700 cm-1) and (Compound II shows absorptions at 3200-3600 and 1650 cm-1) are true.

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

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Which of the following structures is consistent with a compound that displays a molecular ion peak at 56 and infrared signals at 2250 and 3600-3200 cm-1? Which of the following structures is consistent with a compound that displays a molecular ion peak at 56 and infrared signals at 2250 and 3600-3200 cm<sup>-1</sup>?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

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You are given a bottle of an organic liquid and told it must be either cyclohexane or 1-hexene.Which of the following statements is (are) true about these two compounds? You are given a bottle of an organic liquid and told it must be either cyclohexane or 1-hexene.Which of the following statements is (are) true about these two compounds?   A) The two compounds can be differentiated by their mass spectra because they will have molecular ion peaks at different m/z. B) 1-Hexene will show an absorption at 1650 cm<sup>-1</sup> but cyclohexane will not. C) Both cyclohexane and 1-hexene will show C-H absorptions at about 2950 cm<sup>-1</sup>. D) Statements (1-Hexene will show an absorption at 1650 cm<sup>-1</sup> but cyclohexane will not) and (Both cyclohexane and 1-hexene will show C-H absorptions at about 2950 cm<sup>-1</sup>) are both true. E) Statements (The two compounds can be differentiated by their mass spectra because they will have molecular ions at different masses) ,(1-Hexene will show an absorption at 1650 cm<sup>-1</sup> but cyclohexane will not) ,and (Both cyclohexane and 1- hexene will show C-H absorptions at about 2950 cm<sup>-1</sup>) are all true.


A) The two compounds can be differentiated by their mass spectra because they will have molecular ion peaks at different m/z.
B) 1-Hexene will show an absorption at 1650 cm-1 but cyclohexane will not.
C) Both cyclohexane and 1-hexene will show C-H absorptions at about 2950 cm-1.
D) Statements (1-Hexene will show an absorption at 1650 cm-1 but cyclohexane will not) and (Both cyclohexane and 1-hexene will show C-H absorptions at about 2950 cm-1) are both true.
E) Statements (The two compounds can be differentiated by their mass spectra because they will have molecular ions at different masses) ,(1-Hexene will show an absorption at 1650 cm-1 but cyclohexane will not) ,and (Both cyclohexane and 1- hexene will show C-H absorptions at about 2950 cm-1) are all true.

F) B) and C)
G) C) and D)

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Which of the following compounds will have the lowest wavenumber for carbonyl absorption? Which of the following compounds will have the lowest wavenumber for carbonyl absorption?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

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Ignoring sp3 CH stretching,estimate where the major peak be in the following compound's IR. Ignoring sp<sup>3</sup> CH stretching,estimate where the major peak be in the following compound's IR.   A) 3300 cm<sup>-1</sup> B) 3100 cm<sup>-1</sup> C) 2250 cm<sup>-1</sup> D) 1750 cm<sup>-1</sup>


A) 3300 cm-1
B) 3100 cm-1
C) 2250 cm-1
D) 1750 cm-1

E) A) and B)
F) B) and D)

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Ignoring sp3 CH stretching,estimate where the major peak be in the following compound's IR. Ignoring sp<sup>3</sup> CH stretching,estimate where the major peak be in the following compound's IR.   A) 3300 cm<sup>-1</sup> B) 3100 cm<sup>-1</sup> C) 2250 cm<sup>-1</sup> D) 1750 cm<sup>-1</sup>


A) 3300 cm-1
B) 3100 cm-1
C) 2250 cm-1
D) 1750 cm-1

E) B) and D)
F) A) and D)

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