Organic Chemistry, 9e

by L. G. Wade, Jr.

Clicker Questions

Chapter 12
Spectroscopy and
Mass Spectrometry

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 12.1 Identify the region with the longest wavelength.

a) X rays
b) Ultraviolet
c) Visible
d) Infrared
e) Microwave

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 12.1 Identify the region with the longest wavelength.

a) X rays
b) Ultraviolet
c) Visible
d) Infrared
e) Microwave

Explanation:
The wavelength decreases in the order of microwave >
infrared > visible > ultraviolet > X rays.
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 12.2 Identify the region with the highest energy.

a) X rays
b) Ultraviolet
c) Visible
d) Infrared
e) Microwave

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 12.2 Identify the region with the highest energy.

a) X rays
b) Ultraviolet
c) Visible
d) Infrared
e) Microwave

Explanation:
The energy decreases in the order of X rays > ultraviolet >
visible > infrared > microwave.
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 12.3 Which of the following is not one of the infrared
vibrations?

a) Bouncing
b) Wagging
c) Scissoring
d) Rocking
e) Twisting

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 12.3 Which of the following is not one of the infrared
vibrations?

a) Bouncing
b) Wagging
c) Scissoring
d) Rocking
e) Twisting

Explanation:
Bouncing is not an infrared vibration.
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 12.4 Identify the frequency that indicates an alkene.

a) 1660 cm–1
b) 1700 cm–1
c) 2200 cm–1
d) 3300 cm–1

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 12.4 Identify the frequency that indicates an alkene.

a) 1660 cm–1
b) 1700 cm–1
c) 2200 cm–1
d) 3300 cm–1

Explanation:
A carbon–carbon double bond has a stretching frequency at
1660 cm–1.
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 12.5 Identify the frequency that indicates a C—H bond
stretching frequency for an alkane.

a) 1660 cm–1
b) 2900 cm–1
c) 3050 cm–1
d) 3300 cm–1

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 12.5 Identify the frequency that indicates a C—H bond
stretching frequency for an alkane.

a) 1660 cm–1
b) 2900 cm–1
c) 3050 cm–1
d) 3300 cm–1

Explanation:
The C—H bond stretching frequency for an alkane is
2900 cm–1.
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 12.6 Identify the C—H bonding frequency with the
highest wavenumber.

a) sp
b) sp2
c) sp3
d) sp4

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 12.6 Identify the C—H bonding frequency with the
highest wavenumber.

a) sp
b) sp2
c) sp3
d) sp4

Explanation:
The wavenumber decreases in the order of sp > sp2 > sp3.
The sp4 does not exist.
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 12.7 What compound has a formula of C5H8 and a peak at
3300 cm–1?

a) Alkane
b) Alkene
c) Internal alkyne
d) Terminal alkyne

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 12.7 What compound has a formula of C5H8 and a peak at
3300 cm–1?

a) Alkane
b) Alkene
c) Internal alkyne
d) Terminal alkyne

Explanation:
A terminal alkyne has a C—H stretch for —C C–H at
3300 cm–1.
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 12.8 What compound has a formula of C5H12O and a peak
at 3300 cm–1?

a) Ether
b) Alcohol
c) Aldehyde
d) Ketone

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 12.8 What compound has a formula of C5H12O and a peak
at 3300 cm–1?

a) Ether
b) Alcohol
c) Aldehyde
d) Ketone

Explanation:
An alcohol has a very distinct O—H stretch near 3300 cm–1.

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 12.9 What compound has a formula of C6H15N and two
peaks at 3300 cm–1?

a) 1° amide d) 1° amine
b) 2° amide e) 2° amine
c) 3° amide f) 3° amine

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 12.9 What compound has a formula of C6H15N and two
peaks at 3300 cm–1?

a) 1° amide d) 1° amine
b) 2° amide e) 2° amine
c) 3° amide f) 3° amine

Explanation:
A primary amine has two peaks around 3300 cm–1.
An amide has oxygen, which is not in the formula.

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 12.10 What compound has a formula of C5H10O and
peaks at 1710, 2700, and 2800 cm–1?

a) Ketone
b) Aldehyde
c) Ester
d) Carboxylic acid

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 12.10 What compound has a formula of C5H10O and
peaks at 1710, 2700, and 2800 cm–1?

a) Ketone
b) Aldehyde
c) Ester
d) Carboxylic acid

Explanation:
Aldehydes have a C=O stretch at 1710 cm–1 and C—H
stretches at 2700 and 2800 cm–1.
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 12.11 What compound has a formula of C5H10O2, a peak
at 1715, and a broad peak at 3000 cm–1?

a) Aldehyde
b) Ketone
c) Carboxylic acid
d) Ester

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 12.11 What compound has a formula of C5H10O2, a peak
at 1715, and a broad peak at 3000 cm–1?

a) Aldehyde
b) Ketone
c) Carboxylic acid
d) Ester

Explanation:
Carboxylic acids have a C=O stretch at 1715 cm–1 and an
O—H stretch at 3000 cm–1.
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 12.12 In IR spectroscopy, give the effect of C=C
conjugation on the C=O stretch of an aldehyde.

a) It lowers the C=O stretching frequency.

b) It raises the C=O stretching frequency.
c) The C=O stretching frequency is unaffected.
d) The C=O stretching frequency is changed.

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 12.12 In IR spectroscopy, give the effect of C=C
conjugation on the C=O stretch of an aldehyde.

a) It lowers the C=O stretching frequency.

b) It raises the C=O stretching frequency.
c) The C=O stretching frequency is unaffected.
d) The C=O stretching frequency is changed.

Explanation:
The C=O stretching frequency is lowered from about 1710
cm–1 to near 1685 cm–1.
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 12.13 Identify mass spectroscopy.

a) Stretching and bending of bonds

b) Fragmentation of the molecule
c) Interaction between hydrogens
d) Separates mixtures into components

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 12.13 Identify mass spectroscopy.

a) Stretching and bending of bonds

b) Fragmentation of the molecule
c) Interaction between hydrogens
d) Separates mixtures into components

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 12.14 Identify the species measured in mass
spectroscopy.

a) Anions
b) Cations
c) Radicals
d) Cations and radical cations
e) Anions and radical anions

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 12.14 Identify the species measured in mass
spectroscopy.

a) Anions
b) Cations
c) Radicals
d) Cations and radical cations
e) Anions and radical anions

Explanation:
Only cations and radical cations are seen in the mass
spectrometer.
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 12.15 Define base peak.

a) Lowest m/z peak

b) Highest m/z peak
c) Weakest peak
d) Strongest peak

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 12.15 Define base peak.

a) Lowest m/z peak

b) Highest m/z peak
c) Weakest peak
d) Strongest peak

Explanation:
The strongest or tallest peak is the base peak.

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 12.16 Explain why the bromide isotopes are recognizable.

a) The M+2 is half the size of the M.

b) The M+2 is twice the size of the M.
c) The M+2 is the same size as the M.
d) Only one isotope is seen.

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 12.16 Explain why the bromide isotopes are recognizable.

a) The M+2 is half the size of the M.

b) The M+2 is twice the size of the M.
c) The M+2 is the same size as the M.
d) Only one isotope is seen.

Explanation:
The 81Br has a natural abundance of 49.5% while 79Br is
50.5%. The M and the M+2 peaks will be the same size.
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 12.17 Explain why the chloride isotopes are recognizable.

a) The M+2 is one-third the size of the M.

b) The M+2 is three times the size of the M.
c) The M+2 is the same size as the M.
d) Only one isotope is seen.

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 12.17 Explain why the chloride isotopes are recognizable.

a) The M+2 is one-third the size of the M.

b) The M+2 is three times the size of the M.
c) The M+2 is the same size as the M.
d) Only one isotope is seen.

Explanation:
The 37Cl peak is about one-third the size of the 35Cl peak
because their natural abundance is 75% and 25%,
respectively.
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 12.18 Give the fragment at m/z 29 in the mass spectrum of
pentane.

a) CH3CH2•
b) CH3CH2+
c) CH3CH2—
d) CH3CH2

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 12.18 Give the fragment at m/z 29 in the mass spectrum of
pentane.

a) CH3CH2•
b) CH3CH2+
c) CH3CH2—
d) CH3CH2

Explanation:
Only the ethyl cation is seen in the mass spectrum.

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 12.19 Give the fragment at m/z 42 in the mass spectrum of
propan-1-ol.

a) CH3CH=CH2+
b) CH3CH=CH2•
c) CH3CH=CH2—
d) CH3CH=CH2 +•

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 12.19 Give the fragment at m/z 42 in the mass spectrum of
propan-1-ol.

a) CH3CH=CH2+
b) CH3CH=CH2•
c) CH3CH=CH2—
d) CH3CH=CH2 +•

Explanation:
Water is lost from propan-1-ol to form propene as a radical
cation.
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 12.20 Identify a possibility for a fragment at m/z 43 in the
mass spectrum.

a) CH3CH2CH2+
b) CH3CH2CH3+
c) CH2=C=CH2+
d) CH3CH=CH2+

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 12.20 Identify a possibility for a fragment at m/z 43 in the
mass spectrum.

a) CH3CH2CH2+
b) CH3CH2CH3+
c) CH2=C=CH2+
d) CH3CH=CH2+

Explanation:
The only cation with an m/z 43 is propyl.

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