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Chapter 10 review

Ch pter 10 review
Multiple choice (10 MARKS)

Question 1 (1 MARK)
a

When a sample absorbs infrared radiation,

A. covalent bonds are broken. B. covalent bonds stretch and vibrate to a greater extent.
C. the spin alignment of certain nuclei changes. D. electrons in atoms move to higher energy levels.
Adapted from VCAA 2010 Exam 1 Multiple choice Q8

Question 2 (1 MARK)
Which of the following would be the most suitable analytical technique to determine the ratio of
235U to 238U in a sample of uranium metal?

A. Mass spectroscopy B. Infrared spectroscopy

C. High performance liquid chromatography D. Nuclear magnetic resonance spectroscopy
Adapted from VCAA 2010 Exam 1 Multiple choice Q7

Question 3 (1 MARK)
Which one of the following techniques is most suitable for distinguishing between
1,1,1-trichloropropane and 1,2,3-trichloropropane?
A. Infrared spectroscopy B. High resolution 1H-NMR spectroscopy
C. Mass spectrometry D. Chromatography
Adapted from VCAA 2015 exam Multiple choice Q12

Question 4 (1 MARK)
The molecular ion of a compound analysed using mass spectrometry has the symbol [D]+. Some of
the molecular ions fragment according to the following equations.
[D]+ → [X]+ + Y
[D]+ → X + [Y]+
The resulting mass spectrum would show peaks due to
A. D and [D]+. B. D, X, and Y. C. [D]+, [X]+, and [Y]+. D. [X]+ and [Y]+.

Use the following information to answer questions 5–6.

A student is designing an experiment to determine the concentration of aspartame in soft drinks

using high performance liquid chromatography (HPLC). Aspartame, benzoic acid and caffeine are
all common components of soft drinks. Under some conditions, they have similar retention times
in an HPLC column. The graph provided shows the retention times for these substances at different
pH values.
Retention time versus pH
8.5 Key
Retention time (mins)

7.5 Benzoic acid

Aspartame
6.5
Caffeine
5.5
4.5
3.5
2.5
2.5 3.0 3.5 4.0 4.5 5.0
pH

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Question 5 (1 MARK)
According to the graph, which pH value would provide the largest separation of aspartame,
benzoic acid, and caffeine?
A. 3.0 B. 4.0 C. 4.3 D. 4.5
VCAA (NHT) 2019 exam Multiple choice Q8
a

Question 6 (1 MARK)
Which one of the following would minimise sources of error and uncertainty in the
student’s experiment?
A. Dilute the samples of soft drinks prior to analysis by HPLC.
B. Use a different mobile phase for each type of soft drink investigated.
C. Analyse three aliquots of each sample of soft drink through the HPLC instrument.
D. Increase the pH of the samples of soft drinks by adding hydrochloric acid.
VCAA (NHT) 2019 exam Multiple choice Q9

Question 7 (1 MARK)
Petrol is a mixture of hydrocarbon molecules varying in size from six to ten carbon atoms.
Forensic investigators suspect that traces of a substance found at a suspicious fire could be petrol
that was used to start the fire. Which one of the following techniques would be best used to identify
the substance?
A. NMR spectroscopy
B. Infrared spectroscopy
C. High performance liquid chromatography
D. Gas chromatography followed by mass spectroscopy
Adapted from VCAA 2011 Exam 1 Multiple choice Q12

Question 8 (1 MARK)
An unidentified organic substance with the molecular formula C4H8O2 is found to react with a base.
Mass spectrometry shows the parent molecular ion has a mass-to-charge ratio, m/z, of 88.
Which one of the following species is consistent with a peak on the mass spectrum at m/z = 45?
100
Relative intensity (%)

80

60

40

20

0
0 20 40 60 80 100
m/z

A. [COOH]+
B. [CH3CH2O]+
C. [CH3CH2OH]+
D. [CH3CH2CH2COOH]+
VCAA (NHT) 2017 exam Multiple choice Q8

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Question 9 (1 MARK)
Shown below is the infrared spectrum of an organic compound.
100
Transmittance (%)

50 a

0
4000 3000 2000 1500 1000 500
Wave number (cm−1)

The compound consistent with the infrared spectrum is

A. ethanal. B. 2-propanol. C. butan-1-amine. D. octanamide.
Adapted from VCAA 2017 exam Multiple choice Q17

Question 10 (1 MARK)
A high-performance liquid chromatography (HPLC) column has a non-polar stationary phase and
a polar solvent as the mobile phase. Which one of the following substances would have the lowest
retention time?
A. Tetrachloromethane B. Chloromethane C. Bromomethane D. Hexane
VCAA (NHT) 2021 exam Multiple choice Q27

Short answer (30 MARKS)

Question 11 (5 MARKS)
An organic chemist found a bottle in the laboratory that was labelled ‘organic cleaning fluid, C3H8O’.
She decided to test the liquid. The chemist obtained the following data about the compound in the
cleaning fluid: the 1H-NMR and 13C-NMR spectra, and the infrared spectrum. The 1H-NMR data is
summarised in the table provided.

Chemical shift (ppm) Relative peak area Peak splitting

1.2 6 Doublet (2)
2.2 1 Singlet (1)
3.6 1 Septet (7)
1H-NMR spectrum

TMS

6 5.5 5 4.5 4 3.5 3 2.5 2 1.5 1 0.5 0

Chemical shift (ppm)

13C-NMR spectrum

TMS

70 60 50 40 30 20 10 0
Chemical shift (ppm)

a. Consider the NMR spectra shown.

i. How many different carbon environments are present in the compound? 1 MARK
ii. How many different hydrogen environments are present in the compound? 1 MARK
iii. In the 1H-NMR spectrum, the signal at 3.6 ppm is split into a septet.
What is the number of equivalent protons that are bonded to the adjacent carbon atom(s)? 1 MARK

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b. The infrared spectrum obtained is shown.

Absorption

3500 3000 2500 2000 1500 1000 500

Wave number (cm−1)

Identify the atoms that are associated with the absorption peak labelled A on the
infrared spectrum. 1 MARK

c. Draw a structure of the compound in the cleaning fluid that is consistent with the NMR
and IR data. 1 MARK
VCAA 2012 Exam 1 Short answer Q5

Question 12 (6 MARKS)
A mixture containing four straight chain alcohols, S, T, U, and V, each with a general formula ROH,
was analysed using a gas chromatograph combined with a mass spectrometer. The following
chromatogram and peak area data were produced.
T
Alcohol S T U V
U
Peak area (mm2) 900 5000 3900 40
Absorption

S
V

0 0.5 1.0 1.5 2.0

Retention time (min)

The mass spectrum of alcohol T is shown.

100
Relative intensity (%)

80

60

40

20

0
10 15 20 25 30 35 40 45 50 55 60
m/z

a. What is the order of the alcohols from highest molar mass to lowest molar mass? 1 MARK

b. Which of the alcohols is present in the highest concentration? 1 MARK

c. Alcohol T is a primary alcohol. Draw the structural formula of alcohol T. 1 MARK

d. Identify the molecular formula for a fragment ion that could be responsible for the base peak. 1 MARK

e. Explain how gas chromatography and mass spectrometry can be combined to identify the molar
mass of each alcohol present in the mixture. 2 MARKS
Adapted from VCAA 2014 exam Multiple choice Q12,13

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Question 13 (10 MARKS)
A chemist has a sample of an unknown hydrocarbon, Molecule L. The mass spectrum of Molecule
L is shown.
100
Relative intensity (%)

80 a

60

40

20

0
0 10 20 30 40 50 60
m/z

a. Consider the mass spectrum of Molecule L.

i. What is the m/z of the base peak? 1 MARK
ii. What is the molecular formula of Molecule L? 1 MARK
iii. Identify the fragment that produces the peak at 41 m/z. 1 MARK

b. Draw the structural formulas for two isomers of Molecule L. 2 MARKS

c. The chemist finds that Molecule L reacts with hydrogen bromide, HBr, to form two products that
are isomers. The 13C-NMR spectra of the two products are shown below.
Product 1 Product 2

200 180 160 140 120 100 80 60 40 20 0 200 180 160 140 120 100 80 60 40 20 0
Chemical shift ppm Chemical shift ppm

i. Write the semi-structural formula of Molecule L. 1 MARK

ii. The information from the 1H-NMR spectrum of Product 1 is shown in the table.

Chemical shift (ppm) 3.4 1.8 1.5 0.9

Relative peak area 2 2 2 3
Use this information to give the IUPAC systematic name for product 1. 1 MARK

d. Molecule L undergoes a hydration reaction. Spectrum 𝑥 Spectru , m 𝑦 an Spectru

, d m z are the
spectra for three different compounds.
Spectrum x
100
Transmittance (%)

50

0
4000 3000 2000 1500 1000 500
Wave number (cm−1)

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Spectrum y
100
Transmittance (%)

50

0
4000 3000 2000 1500 1000 500
Wave number (cm−1)

Spectrum z
100
Transmittance (%)

50

0
4000 3000 2000 1500 1000 500
Wave number (cm−1)

Which of the spectra shown is consistent with a product of the hydration reaction for
Molecule L? Your answer should make reference to the information in the spectra. 3 MARKS

VCAA (NHT) 2021 exam Short answer Q8

Question 14 (9 MARKS)
A small organic molecule has the molecular formula of the form C𝑥H𝑦O2Cl. A pH probe was inserted
into a dilute aqueous solution of this compound, and the pH was 4.5. The mass spectrum, infrared
spectrum, 13C-NMR spectrum, and low resolution 1H-NMR spectrum of this compound are provided.
CxHyO2Cl mass spectrum
100 Isotope data
Relative intensity (%)

1H : 2H = 99.99 : 0.01
80
12C : 13C = 98.93 : 1.07
60 35Cl : 37Cl = 75.78 : 24.22

40

20

0 10 20 30 40 50 60 70 80 90 100 110 120

m/z

IR spectrum
100
Transmittance (%)

50

0
4000 3000 2000 1500 1000 500
Wave number (cm−1)

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13C-NMR spectrum

TMS

180 160 140 120 100 80 60 40 20 0

Chemical shift (ppm) a

1H-NMR spectrum

TMS

12 10 8 6 4 2 0
Chemical shift (ppm)

a. Identify two peaks on the infrared spectrum that correspond to the presence of functional
groups in this compound. Note: The peak due to the C−Cl stretch has already been labelled. 2 MARKS

b. Use the data provided to determine the values of an 𝑥 d 𝑦 i C𝑥H𝑦O2Cl.

n 2 MARKS

c. The splitting patterns shown on the high resolution 1H-NMR spectrum of the compound are
given in the following table.

Chemical shift (ppm) 1.7 4.5 11.2

Peak splitting Doublet Quartet Singlet

i. What specific information about the structure of the compound is provided by the
integration curves on the low resolution 1H-NMR spectrum? 1 MARK
ii. What specific information about the structure of the compound is provided by the splitting
patterns in the high resolution 1H-NMR spectrum? 1 MARK
iii. Draw the structural formula for this molecule. 1 MARK

d. Give a reason why the mass spectrum shows two molecular ion peaks, one at m/z = 108 and
one at m/z = 110, rather than just one. In your answer, give the semi-structural formulas for
the compounds responsible for each molecular ion peak. 2 MARKS
Adapted from VCAA 2014 exam Short answer Q4

Key science skills (10 MARKS)

Question 15 (7 MARKS)
Caffeine is a stimulant drug that is found in coffee, tea, energy drinks, and some soft drinks.
The concentration of caffeine in drinks can be determined using high performance liquid
chromatography (HPLC). The retention time of caffeine is 96 seconds.
Four caffeine standard solutions containing 50 ppm, 100 ppm, 150 ppm, and 200 ppm of caffeine
were prepared. 25 µL of each sample was injected into the HPLC column. The peak areas for each
standard solution are given in the following table.

Concentration of caffeine 50 100 150 200

standard solution (ppm)
Peak area 4000 9400 14 100 18 700
a. Construct a calibration curve for the caffeine standard solutions. 3 MARKS

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b. 25 µL samples of three drinks thought to contain caffeine were then separately passed through
the HPLC column. The results are summarised in the table provided.

Sample Retention time of major peak (seconds) Peak area of largest peak
Energy drink 96 12 000
a

Soft drink 32 8500

Espresso coffee 96 211 000
Use your calibration curve from part a to determine the concentration of caffeine, in ppm,
in the energy drink. 1 MARK

c. The chromatograms of each drink are given.

Standard (50 ppm) Energy drink

20 20
Peak area

Peak area
(× 1000)

(× 1000)
15 15
10 10
5 5

0 10 20 30 40 50 60 70 80 90 100 110 120 10 20 30 40 50 60 70 80 90 100 110 120

Time (s) Time (s)

Soft drink Espresso coffee

20 20
Peak area
(× 1000)

Peak area

15
(× 1000)

15
10 10
5 5

0 10 20 30 40 50 60 70 80 90 100 110 120 0 10 20 30 40 50 60 70 80 90 100 110 120

Time (s) Time (s)

i. According to the chromatogram, does the soft drink contain caffeine? Explain. 1 MARK
ii. Explain why the caffeine content of the espresso coffee sample cannot be reliably
determined using the information provided. 1 MARK
iii. Describe what could be done to the espresso coffee sample so that its caffeine content can
be determined using the information provided. 1 MARK

Adapted from VCAA 2011 Exam 1 Short answer Q3

FROM LESSONS 12B, 12C & 12E

Question 16 (3 MARKS)
The composition of fatty acids found in an egg yolk sample is given in the following table.

Fatty acid Percentage (%)

Palmitic 25.9
Stearic 9.1
Palmitoleic 3.4
Oleic 40.9
Linoleic 16.3
Linolenic 2.9
Arachidonic 1.5
The composition of fatty acids in an egg yolk was determined by reacting the fatty acids with
methanol to produce methyl esters and then analysing the methyl esters using chromatography.
Explain, using the principles of chromatography, how each fatty acid in the egg yolk sample can be
identified and the percentage determined.
Adapted from VCAA 2020 exam Short answer Q7bi

FROM LESSONS 12B & 12E

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