Smith6e SpectroscopyB TB AnswerKey

Organic Chemistry, 6e (Smith)
Spectroscopy B Infrared Spectroscopy
1) 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
Answer: A
Difficulty: 1 Easy
Section: B.02
Topic: Analytical/Spectroscopy
Bloom's: 1. Remember
Chapter: Spectroscopy B
Accessibility: Keyboard Navigation
2) The functional group region of an infrared spectrum is

A) where the cations appear.
B) greater than or equal to 1500 cm–1.
C) less than 1500 cm–1.
D) greater than or equal to 2500 cm–1.
Answer: B
Difficulty: 1 Easy
Section: B.02
Bloom's: 1. Remember
3) Stronger bonds will be found where in the infrared spectrum?

A) Higher molecular weight
B) Lower molecular weight
C) Lower wavenumbers
D) Higher wavenumbers
Answer: D
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
1
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4) 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
Answer: C
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
5) Why does an alkyne carbon–carbon triple bond vibrate at a higher wavenumber than an alkene
carbon–carbon double bond?
A) It is stronger.
B) It is weaker.
C) It has fewer hydrogens.
D) It makes a less stable cation.
Answer: A
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
6) 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.
Answer: C
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
2
7) 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–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.
Answer: D
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
8) In an IR spectrum, which of the indicated C–H bonds exhibits a stretching absorption at the
largest wave number?
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
3
9) 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–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.
Answer: D
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
10) 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
Answer: C
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
4
11) Which of the following statements is (are) true about the IR spectrum of the compound
drawn below?
A) It shows absorptions at 3000–3150 cm–1 and 1720 cm–1.

B) It shows absorptions at 3000–2850 cm–1 and 2150 cm–1.
C) It shows absorptions at 2250 cm–1 and 1650 cm–1.
D) It shows absorptions at 2250 cm–1 and 1720 cm–1.
E) Both statements (It shows absorptions at 3000–2850 cm–1 and 2250 cm–1) and (It shows
absorptions at 2250 cm–1 and 1720 cm–1) are true.
Answer: E
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
12) A compound X shows a molecular ion peak at m/z 72 in its mass spectrum, and a strong peak
at ~1715 cm–1 in its IR spectrum. Which structures are possible for compound X?
A) I
B) II
C) III
D) I and II
Answer: A
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
5
13) 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–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.
Answer: D
Difficulty: 2 Medium
Section: B.05
Bloom's: 3. Apply
14) 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.
Answer: A
Section: B.05
Bloom's: 3. Apply
6
15) An alkyne C–H bond absorbs at higher wave number than an alkene C–H bond. What does
this tell you about the strength of these two bonds?
A) The alkene C–H bond is stronger.
B) The alkyne C–H bond is stronger.
C) The alkene C–C bond is stronger.
D) The alkyne C–C bond is stronger.
Answer: B
Section: B.03
Bloom's: 3. Apply
16) Which of the following statements is (are) true about a compound that has a molecular ion
peak in its mass spectrum at mass 94 and shows prominent peaks in its IR spectrum at 3600–
3200 and 1600 cm–1?
B) The compound contains a C=O group and Csp3-H hybridized bonds.
C) The compound contains an OH group and a benzene ring.
D) Both (The compound has a molecular mass of 94) 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 94) and (The compound contains an OH group
and a benzene ring) are true statements.
Answer: E
Section: B.05
Bloom's: 3. Apply
7
17) Which of the following statement(s) is (are) true about a compound that has a molecular ion
peak in its mass spectrum at mass 69 and shows a prominent peak in its IR spectrum at 2250 cm–
1?
B) The compound contains a C=O group.
C) The compound contains a cyano or alkyne group.
D) Both (The compound has a molecular mass of 70) and (The compound contains a C=O group)
are true statements.
E) Both (The compound has a molecular mass of 70) and (The compound contains a cyano or
alkyne group) are true statements.
Answer: C
Section: B.05
Bloom's: 3. Apply
18) 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.
Answer: B
Section: B.05
Bloom's: 3. Apply
8
19) Which of the following structures is consistent with a compound that displays a molecular
ion peak at 103 and infrared signals at 2250 and 1600 cm–1?
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: B.05
Bloom's: 3. Apply
ion peak at 56 and infrared signals at 2250 and 3600–3200 cm–1?
A) I
B) II
C) III
D) IV
Answer: B
Section: B.05
Bloom's: 3. Apply
9
ion peak at 84 and infrared signals at 3000–2850 cm–1 and no signals between 3000-3300 cm-1?
A) I
B) II
C) III
D) IV
Answer: D
Section: B.05
Bloom's: 3. Apply
22) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the
following compound?
A) A signal at 1600 cm–1

B) A signal at 3300 cm–1
C) A single mass peak at 92 amu
D) Two mass peaks at 92 and 94 amu
Answer: D
Difficulty: 1 Easy
Section: B.05
Bloom's: 3. Apply
10
23) 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–1
D) A signal at 1720 cm–1
Answer: D
Difficulty: 1 Easy
Section: B.05
Bloom's: 3. Apply
24) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the
following compound?
A) A signal at 95 amu
B) A signal at 94 amu
C) Two signals at 95 and 94 amu
D) A signal at 3600–3200 cm–1
Answer: A
Section: B.05
Bloom's: 3. Apply
11
25) Examine the IR below and classify the compound.
A) Alkane
B) Carboxylic acid
C) Alcohol
D) Alkene
Answer: C
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
12
A) Alcohol
B) Aldehyde
C) Amine
D) Ketone
E) Carboxylic acid
Answer: D
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
13
A) Alcohol
B) Arene
C) Amine
D) Ketone
E) Carbocylic acid
Answer: B
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
14
A) Alcohol
B) Aldehyde
C) Carboxylic acid
D) Ketone
Answer: C
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
15
A) Alcohol
B) Aldehyde
C) Amine
D) Ketone
Answer: C
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
16
30) 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.
A) I
B) II
C) III
D) IV
Answer: C
Section: B.05
Bloom's: 3. Apply
17
31) The base peak in a mass spectrum corresponds to the most stable fragment. Propose a
structure for a compound that is consistent with the following data.
a) The molecular ion peak has m/z = 116.
b) The base peak is at m/z = 59.
c) The compound is composed of C, H and O atoms.
d) The IR spectrum shows a strong absorbance at 3257 cm-1.
A) I
B) II
C) III
D) IV
Answer: D
Section: B.05
Bloom's: 3. Apply
18
32) 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.
A) I
B) II
C) III
D) IV
Answer: D
Section: B.05
Bloom's: 3. Apply
33) When the phenol shown below is treated with KOH, it forms a product whose IR spectrum
does not show an absorption in the 3200-3600 cm-1 region. Propose a structure for the product.
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: B.05
Bloom's: 3. Apply
19
20
34) 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.
Answer: B
Difficulty: 1 Easy
Section: B.02
Bloom's: 2. Understand
35) Which of the following compounds will have the lowest wavenumber for carbonyl
absorption?
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: B.03
Bloom's: 3. Apply
21
36) Which of the following π bonds is IR inactive?
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: B.02
Bloom's: 3. Apply
37) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s
IR.
A) 3300 cm-1
B) 3100 cm-1
C) 2250 cm-1
D) 1750 cm-1
Answer: A
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
22
IR.
A) 3300 cm-1
B) 3100 cm-1
C) 2250 cm-1
D) 1750 cm-1
Answer: D
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
IR.
A) 3300 cm-1
B) 3100 cm-1
C) 2250 cm-1
D) 1750 cm-1
Answer: C
Difficulty: 1 Easy
Section: B.04
Bloom's: 3. Apply
23

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Organic Chemistry, 6e (Smith)

Spectroscopy B Infrared Spectroscopy

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

2) The functional group region of an infrared spectrum is

3) Stronger bonds will be found where in the infrared spectrum?

A) I shows strong absorptions at 2950 cm–1 and 1700 cm–1.

A) Compound I shows absorptions at 2950 and 1700 cm–1.

A) It shows absorptions at 3000–3150 cm–1 and 1720 cm–1.

A) A signal at 1600 cm–1

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.

a) The molecular ion peak has m/z = 116.

b) The base peak is at m/z = 59.

c) The compound is composed of C, H and O atoms.

d) The IR spectrum shows a strong absorbance at 3257 cm-1.

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