10/15/22, 12:16 PM CH12-HW#1

CH12-HW#1
Due: 11:59pm on Saturday, October 15, 2022
You will receive no credit for items you complete after the assignment is due. Grading Policy

Chapter 12 Reading Quiz Question 1

Part A
Which of the following four regions of the electromagnetic spectrum is LOWEST in energy?

Hint 1. The electromagnetic spectrum

Although all electromagnetic radiation travels at a constant speed in a vacuum, the energy of the radiation is variable. The electromagnetic spectrum organizes light into various
classifications on this basis. See 12-2.

ANSWER:

Ultraviolet

Radio wave

X-ray

Microwave

Correct

Chapter 12 Reading Quiz Question 2

Part A
Express the wavelength of 500 nm (green light) in units of wavenumbers.

Hint 1. Wavenumbers

The wavenumber (cm−1) is a common unit used in infrared spectroscopy. It corresponds to the number of wavelengths that would fit in 1 cm. See 12-3.

ANSWER:

2 × 106 cm−1

2 × 102 cm−1

2 cm−1

2 × 104 cm−1

Correct

Chapter 12 Reading Quiz Question 3

Part A
Which bond will vibrate at the highest frequency?

Hint 1. Molecular vibrations

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Remember that molecular vibrations can be envisioned as similar to weights vibrating on springs; the masses of the atoms relate to the masses of the weights, and the stiffness of the
springs relates to the bond strengths. See 12-4.

ANSWER:

Correct

Assignment of IR Absorption Features

Learning Goal:
To learn to correlate peaks in infrared spectra to common functional groups in organic molecules

The assignment of absorption bands in an infrared (IR) spectrum is aided by the ball-and-spring model of molecular vibrations. According to the model, atoms of a functional group can be
thought of as two masses connected by a "spring" (the chemical bond) with force constant k that is related to bond strength. The strength of the bond and types of atoms it connects determines
the frequency of the vibration (via Hooke's law). Vibrations can be due to stretching modes of the chemical bond or bending modes about the bond angles. Each mode occurs at specific
frequency and when a molecule is subjected to IR radiation of the same frequency absorption occurs. Stretching vibrations occur at higher frequencies than bending vibrations and these
vibrations tend to be more characteristic and predictable than the bending vibrations. We will concentrate on these stretching modes. These generally occur in an IR spectrum at wavenumbers
higher than 1400 cm−1 . This region is called the functional group region and allows one to make relative assignments of absorption bands to particular functional groups.

The two main features of IR absorption bands used to make assignments are location and intensity. Location depends upon both atom type and bond strength; intensity is a function of atom
type.

Band location

In the ball-and-spring model, the force constant provides a measure of bond strength. Stronger springs have larger force constants than weaker springs, and they vibrate faster. By analogy,
stronger bonds vibrate at a higher frequency (have a larger wavenumber in an IR spectrum) than weaker bonds. Therefore, triple bonds absorb at higher frequencies than single bonds. In
addition, springs connecting small masses vibrate faster than springs connecting large masses. Therefore, a C−H bond will vibrate at a higher frequency than a C−O bond.

Part A
Rank the following bonds from highest to lowest stretching frequency.

Rank from highest to lowest. To rank items as equivalent, overlap them.

Hint 1. How to approach the problem

First determine the relationship between bond strength and vibrational frequency. Use this relationship to predict which bonds have a higher stretching frequency. Recall that a higher
stretching frequency is the evidenced in an IR spectrum as an IR peak at a higher wavenumber.

Hint 2. Rank bond strengths of single, double, and triple bonds

Rank the strengths of the following bonds from strongest to weakest.

Rank from strongest to weakest. To rank items as equivalent, overlap them.

ANSWER:

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Strongest bond Weakest bond

Hint 3. Correlate bond strength to stretching frequency

Which of the following best explains the relationship between bond strength and stretching frequency?

ANSWER:

The stronger the bond the higher the stretching frequency.

The stronger the bond the lower the stretching frequency.

ANSWER:

Reset Help

Highest stretching frequency Lowest stretching frequency

The correct ranking cannot be determined.

Correct
When looking at an IR spectra, note that a higher stretching frequency is equivalent to a higher wavenumber. For example, a carbon-carbon double bond is located around 1600
−1
cm or somewhat higher, and a carbon-carbon triple bond is located around 2100 cm−1 or somewhat higher.

Part B
Rank the following bonds from highest to lowest IR stretching frequency.

Rank from highest to lowest. To rank items as equivalent, overlap them.

Hint 1. How to approach the problem

First determine the relationship between the masses of the bonded atoms and the resulting frequency of vibration. Use this relationship to predict which species have a higher
stretching frequency. Recall that a higher stretching frequency is the same as an IR peak at a higher wavenumber.

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Hint 2. Correlate stretching frequency to atomic mass

Stretching frequency is inversely proportional to mass. When considering masses connected by a spring with the same value of k, the heavier atoms will not vibrate as quickly as the
lighter ones when the same force is applied.

Assuming that the bonds shown below have a similar values of k, which has the higher stretching frequency?

ANSWER:

C−O

C−C

ANSWER:

Reset Help

Highest stretching frequency Lowest stretching frequency

The correct ranking cannot be determined.

Correct

Band intensity

The intensity of an IR absorption band depends upon the magnitude of the dipole moment of the bond and how it changes upon vibration. A large dipole moment, resulting from a large
difference in electronegativity between bonded atoms, produces a stronger absorption band than a bond with a smaller dipole moment. As a result, a C−H bond will have a more intense
absorption than a C−C bond.

Part C
Sort the following functional groups based on IR absorption band intensity.

Drag the appropriate functional groups to their respective bins.

Hint 1. How to approach the problem.

First determine the relationship between the change in dipole that occurs during a vibration and the resulting intensity of an absorption in an IR spectrum. Use this relationship to
predict the relative intensities of each IR band. Recall that a higher stretching frequency is the same as an IR peak at a higher wavenumber.

Hint 2. Rank relative electronegativities

Rank the magnitude of the electronegativities from greatest to least.

Rank from greatest to least. To rank items as equivalent, overlap them.

ANSWER:

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Greatest Least

O N C

Hint 3. Rank relative dipole moments

A bond dipole is based on a difference in electronegativities between the two atoms involved in the bond. The greater the difference in electronegativities, the larger the magnitude of
the bond dipole.
Rank the dipole moment experienced across the following bonds from greatest to smallest.

Rank from greatest to smallest. To rank items as equivalent, overlap them.

ANSWER:

Reset Help

Greatest bond dipole moment Smallest bond dipole moment

ANSWER:

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Strong Medium Weak

Correct
A bond with a large dipole moment produces a stronger absorption band than a bond with a smaller dipole moment. The carbon-carbon bonds will have peaks with a high percent
transmittance, little absorption, whereas the oxygen-hydrogen, carbon-oxygen, and carbon-nitrogen bonds will have significantly stronger absorption resulting in a more intense
peak in the IR spectrum.

Part D
Tables of data relating bonds and functional groups to the wavenumber of IR absorptions are the tools used to relate IR absorptions to the functional groups present in the sample. An
abbreviated version showing some important bond types is shown below.
Type of bond Wavenumber (cm−1 ) Intensity

C ≡ N 2260-2220 medium

C ≡ C 2260-2100 medium to weak

C = C 1680-1600 medium

C = N 1650-1550 medium
aromatic ~1600 and ~1500-1430 strong to weak

C = O 1780-1650 strong

C−O 1250-1050 strong

C−N 1230-1020 medium

O−H (alcohol) 3650-3200 strong, broad

OH (carboxylic acid) 330-2500 strong, very broad

N−H 3500-3300 medium, broad

C−H 3300-2700 medium

Based on this data, assign the following functional groups to the peaks in the IR spectrum provided.

Identify the peaks by dragging the appropriate labels to their respective targets.

Hint 1. How to approach the problem

Examine both the position of the IR absorption band (measured using the wavenumber scale along the x-axis) and the intensity of the band (measured by the %Transmittance scale
along the y -axis). Relate these to the tabulated values for the various functional groups.

Hint 2. Determine relative locations of IR absorption bands

Which statements are true concerning the relative locations of IR absorption bands.

Check all that apply.

ANSWER:

Atoms connected by stronger bonds vibrate at higher frequencies than the corresponding atoms connected by weaker bonds.

Atoms connected by stronger bonds vibrate at lower frequencies than the corresponding atoms connected by weaker bonds.

Bonds between heavy atoms vibrate at higher frequencies than bonds between light atoms.

Bonds between heavy atoms vibrate at lower frequencies than bonds between light atoms.

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Hint 3. Determine relative intensities of IR absorption bands

Sort each of the following sentences describing bond dipoles by the expected change.
Drag the appropriate sentences to their respective bins.
ANSWER:

Reset Help

Increases Decreases

The magnitude of a bond dipole as the

The intensity of an IR transition as the
electronegativity between the bonded
bond dipole decreases.
atoms increases.

ANSWER:

Reset Help

Correct

Chapter 12 Reading Quiz Question 4

Part A

Which of the following compounds will display IR absorbance in the region of 3000–3010 cm−1?

You did not open hints for this part.

ANSWER:

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[2.2.1]-bicycloheptane

1,2-dimethylcyclohexene

3-methylbut-1-yne

trans-pent-2-ene

Acidity: Complete the statement about the IR spectra of the nitrophenol compounds

Part A

Drag the appropriate labels to their respective targets. Use only pink labels for pink targets.

ANSWER:

Reset Help

compound 2
(p-nitrophenol)

compound 3
(m-nitrophenol)

strong van der Waals compound 1 strong intramolecular

Group 1
(o-nitrophenol) Group
hydrogen 2
bonding
interactions

strong intermolecular
hydrogen bonding

Correct
Intramolecular hydrogen bonding in this molecule reduces the degree of intermolecular hydrogen bonding. This causes the broad band usually seen in alcohols and phenols due to
intermolecular hydrogen bonding to diminish.

Chapter 12 Reading Quiz Question 5

Part A

Which of the following compounds will have an intense IR absorbance in the region of 1710–1725 cm−1?

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Hint 1. Characteristic stretching frequencies of functional groups

IR spectroscopy is very useful as a qualitative tool to determine the presence or absence of certain functional groups. Consequently, it is a good idea to become familiar with the
characteristic frequencies given in Table 12-2. See 12-9.

ANSWER:

Correct

IR Spectroscopy: use the IR Spectra to draw the the structure of C5H8O

Part A
The IR spectrum of a compound with molecular formula C5H8O was obtained in CCl4 and is shown in the figure. Identify the compound.

Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default.
ANSWER:

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Problem 12-6

For each spectrum, interpret all the significant stretching frequencies above 1580 cm−1 .

Part A

Assign the major peaks above 1580 cm−1 .

Identify the major peaks by dragging the appropriate labels to their respective targets.
ANSWER:

Reset Help

saturated
overtone C=C C ≡ C−H O−H C=O C≡C C = C−H N−H O = C−H C−O
C−H

Part B

Assign the major peaks above 1580 cm−1 .

Identify the major peaks by dragging the appropriate labels to their respective targets.
ANSWER:

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saturated
C−O O = C−H O−H N−H C=C overtone C ≡ C−H C=O C≡C C = C−H
C−H

Part C
Assign the major peaks above 1580 cm−1 .
Identify the major peaks by dragging the appropriate labels to their respective targets.

ANSWER:

Reset Help

saturated
C=O overtone C−O O = C−H N−H C≡C C=C C = C−H O−H C ≡ C−H
C−H

Part D

Assign the major peaks above 1580 cm−1 .

Identify the major peaks by dragging the appropriate labels to their respective targets.
ANSWER:

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saturated
C = C−H C=O C=C overtone O = C−H C≡C C−O N−H O−H C ≡ C−H
C−H

Spectroscopy: Choose the compound that matches the IR spectra (I)

Part A
Choose the compound responsible for the IR spectrum shown.

ANSWER:

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Spectroscopy: Choose the compound that matches the IR spectra (III)

Part A
Choose the compound responsible for the IR spectrum shown.

ANSWER:

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Spectroscopy: Choose the compound that matches the IR spectra (VI)

Part A
Choose the compound responsible for the IR spectrum shown.

ANSWER:

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Topic IR Spectroscopy - part 1

Part A
One of the following compounds is responsible for the IR spectrum shown. Choose the structure of the responsible compound.

ANSWER:

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Topic IR Spectroscopy - part 6

Part A
One of the following compounds is responsible for the IR spectrum shown. Choose the structure of the responsible compound.

ANSWER:

Topic IR Spectroscopy - part 9

Part A
One of the following compounds is responsible for the IR spectrum shown. Choose the structure of the responsible compound.

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ANSWER:

Score Summary:
Your score on this assignment is 32.4%.
You received 7.78 out of a possible total of 24 points.

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