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Worked solutions to student book questions

Chapter 6 Chromatography
Q1.
An extract from a plant was analysed using thin-layer chromatography with a nonpolar solvent. The chromatogram obtained is shown in Figure 6.4.

Yellow
Orange
Dark green
Light green

Figure 6.4
Chromatogram.

Table 6.2 gives the Rf values of some chemicals commonly found in plants.
Table 6.2 Rf values of some plant materials.

Chemical
Xanthophyll
-Carotene
Chlorophyll a
Chlorophyll b
Leutin
Neoxanthin
a
b
c
d

Rf
0.67
0.82
0.48
0.35
0.39
0.27

Measure and record the distance from the origin to the centre of each band, and
the distance of the solvent front from the origin.
Calculate the Rf value of each band.
Compare Rf values for the bands to the Rf values in Table 6.2 and name the
chemicals present in the extract.
If water had been used as the solvent, would the chromatogram be likely to have
been similar in appearance? Explain.

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Chapter 6 Chromatography
A1.
a, b, c It would be useful to set your answers out in a table.
Band
Light green
Dark green
Orange
Yellow
Solvent front
d

a Distance from
origin (mm)
20
27
40
50
60

b Rf

c compound

0.33
0.45
0.67
0.83

Chlorophyll b
Chlorophyll a
Xanthophyll
-Carotene

The chromatogram would be likely to be different because separation of


components depends on their solubility in the mobile phase (as well as strength of
adsorption to the stationary phase). The polarity of the solvent used in TLC and
paper chromatography will affect the Rf of the sample components. A polar
solvent will dissolve polar samples readily; a non-polar solvent will dissolve nonpolar samples readily.

E1.
Solids are not injected into the inlet port of a gas chromatograph. How might the
chromatograms of the chips have been obtained?
AE1.
A sample of air from near the chips may have been injected into the inlet port of the
gas chromatograph. Alternatively, the chips may have been mashed and mixed with a
solvent that would cause the compounds responsible for the off-flavours to dissolve;
this solution would then have been injected into the instrument.
E2.
What method was used to confirm that new peaks in the chromatogram of the offflavoured chips could be attributed to the substances that caused the disagreeable
flavour?
AE2.
The effluent from the column was smelt and compared with the smell of the offflavoured chips.
E3.
What recommendations would you make to overcome the problem at the factory?
AE3.
To prevent further problems at the factory, regular inspections for the presence of soft
rot on the stored potatoes should be conducted; potatoes should be stored under
conditions that minimise the problem of soft rot.

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Worked solutions to student book questions

Chapter 6 Chromatography
Q2.
Australian wines are routinely tested for ethanol content. A quick and reliable method
is by gasliquid chromatography. The peak areas produced by a sample of wine and a
number of standard solutions of ethanol are shown in Table 6.3.
Table 6.3 Peak areas from GLC analysis of a wine sample and standards.

Wine
Standard 1
Standard 2
Standard 3
Standard 4
a
b
c

% ethanol
?
4.00
8.00
12.0
16.0

Relative ethanol peak area


82 400
31 200
62 900
94 200
125 700

Plot a calibration curve of concentration of ethanol against peak area.


Determine the percentage of ethanol in the wine sample.
Why is it necessary to measure the peak areas produced by a number of
standards?

A2.
a

b
c

10.4%
Techniques such as AA, GLC, HPLC, UV, etc. do not directly produce measures
of concentration. Standards must be used. More than one standard should be used
and the unknown sample should lie between these standards. This is because a
zero standard may be contaminated with trace amounts of the chemical being
tested. Calibration graphs are often non-linear and multiple standards increase the
chance of detecting incorrectly prepared solutions.

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Worked solutions to student book questions

Chapter 6 Chromatography
Chapter review
Q3.
Write a definition of each of the following terms: adsorption, desorption, mobile
phase, stationary phase, eluent, retention time, carrier gas.
A3.
adsorption The attraction of one substance to the surface of another.
desorption The breaking of the bonds between a substance and the surface to which
the substance is adsorbed.
mobile phase The phase that moves over the stationary phase in chromatography.
stationary phase A solid, or a solid that is coated in a viscous liquid, used in
chromatography. The components of a mixture undergo adsorption to this phase as
they are carried along by the mobile phase.
eluent A liquid used as the mobile phase in chromatography.
retention time The time taken for a component to pass through a chromatography
column.
carrier gas The gas used as the mobile phase in gas chromatography.
Q4.
There are several types of chromatography, including thin-layer and paper, gas and
high performance liquid chromatography. What features are common to all kinds of
chromatography?
A4.
All chromatographic techniques involve a stationary phase, mobile phase and
separation of components.
Q5.
a

Use the terms adsorbed and absorbed correctly in each of the sentences below.
i Water was __________ by the towel as the wet swimmer dried himself.
ii A thin layer of grease ___________ onto the cup when it was washed in the
dirty water.
Explain the difference between the two terms adsorbed and absorbed.

A5.
a
b

Water was absorbed by the towel as the wet swimmer dried himself.
A thin layer of grease adsorbed onto the cup when it was washed in the dirty
water.
Adsorb Atoms or molecules accumulate and bond weakly to the surface of a
solid or liquid.
Absorb atoms or molecules are taken into the material.

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Chapter 6 Chromatography
Q6.
Phenacetin was once included in analgesic drugs, but is not used now because it
causes liver damage. It is soluble in chloroform. A chemist wishes to analyse a brand
of analgesic using thin-layer chromatography to determine whether it contains
phenacetin. Outline the steps in the analysis. (Assume that a sample of pure
phenacetin is available to the chemist.)
A6.
1
2
3
4
5
6

Dissolve a sample of pure phenacetin in a volume of chloroform. This is the


standard solution.
Dissolve a tablet of the analgesic in chloroform. This is the sample solution.
Place a small spot of the sample solution near the bottom of a thin-layer plate.
Place a spot of the standard solution next to it, at the same distance from the
bottom of the plate.
When the spots are dry, place the plate in a container with a small volume of
solvent, such as chloroform or another organic solvent. The lower edge of the
plate, but not the spots, should be immersed.
Allow the solvent to rise until it almost reaches the top of the plate and remove
the plate from the container.
Let the plate dry and examine it under ultraviolet light. If a spot from the sample
appears at the same distance from the origin as the spot from the standard
solution, the tablet is likely to contain phenacetin.

Q7.
A sample of brown dye from a lolly is placed at the origin on a strip of a
chromatography plate. The solvent front moves 9.0 cm from the origin. A blue
component of the dye moves 7.5 cm and a red component 5.2 cm in the same time.
Calculate the Rf values of the two components.
A7.
Rf = distance dye has moved/distance solvent front has moved.
Blue dye Rf =
Red dye Rf =

7.5
9.0
5.2
9.0

= 0.83
= 0.58

Q8.
Consider the diagram of thin-layer chromatography of three food colours in Figure 6.2
on page 63 of the student book.
a Why must the level of the solvent be lower than the origin where spots of the
mixture are originally placed?
b Why are Rf values always less than one?
c How many different components have been used to make colour A?
d Which components present in colours B and C are also in colour A? Explain.
e Which component of colour A is most strongly adsorbed on the stationary phase?
f Calculate the Rf values of each component of colour C.

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Chapter 6 Chromatography
A8.
a
b
c
d
e
f

If the solvent were above the level of the origin, the compounds under test would
dissolve and disperse throughout the solvent.
Components in a mixture undergoing chromatography cannot move faster than
the solvent that is carrying them over the stationary phase. Rf values must
therefore be less than one.
3
B: blue; C: green. They can be identified on the basis of their colour and Rf values.
blue
0.63; 0.13

Q9.
Thin-layer chromatography showed that the black dye used in a brand of writing ink
contained blue, red, orange and yellow components. The Rf values of these substances
using ethanol as the solvent are 0.59, 0.32, 0.80 and 0.19, respectively.
a How far apart would the blue and yellow components be after the solvent front
had moved 8.0 cm from the origin?
b When the red component had travelled 6.0 cm from the origin, how far would the
orange component have travelled?
c Sketch the chromatogram of the ink to scale after the solvent front had moved
15 cm from the origin.
A9.
a
b
c

3.2 cm
15 cm
See diagram below.

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Chapter 6 Chromatography
Q10.
The amino acids present in a sample of fruit juice can be detected by thin-layer
chromatography. Rf values of some amino acids using two separate solvents are given
in Table 6.4.
Table 6.4

Amino acid
Lysine
Leucine
Proline
Valine
2-Aminobutyric acid
Threonine
Hydroxyproline
-Phenylamine
Isoleucine
Alanine
Serine
Glutamic acid
Glycine
Arginine
Taurine
Tyrosine

Solvent 1 Rf
0.12
0.58
0.39
0.40
0.28
0.21
0.21
0.50
0.57
0.24
0.19
0.25
0.20
0.13
0.12
0.38

Solvent 2 Rf
0.55
0.82
0.88
0.74
0.58
0.49
0.67
0.86
0.81
0.55
0.34
0.33
0.40
0.60
0.33
0.62

To achieve better separation of the complex mixture of substances present in the juice,
a two-way chromatogram was prepared. The first step in this procedure was to run a
chromatogram using Solvent 1. The results of this chromatogram are shown in
Figure 6.17.

Figure 6.17

a
b

Calculate the Rf value of each spot on the chromatogram.


Try to identify the amino acids responsible for each spot.

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Chapter 6 Chromatography
The paper was then turned around so that it lay at a right angle to the original and a
second chromatogram was run using Solvent 2. Figure 6.18 shows the appearance of
the paper after some time.
c Use the table of Rf values to identify each component in the mixture.
d What is the advantage of a two-way chromatogram?

Distance (cm)

Figure 6.18

A10.
a
b
c
d

A: 0.59; B: 0.49; C: 0.38; D: 0.20; E: 0.13


A: leucine and/or isoleucine; B: -phenylamine; C: proline and/or valine and/or
tyrosine; D: threonine and/or hydroxyproline and/or serine and/or glycine;
E: lysine and/or arginine and/or taurine
A: leucine and/or isoleucine; B: -phenylamine; C: proline; D: serine; E: arginine
A two-way chromatogram produces better separation of components of complex
mixtures, permitting easier isolation and identification.

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Chapter 6 Chromatography
Q11.
Read the following article from a 1990 British magazine and answer the questions.
Forensic expert slates Maguire analysis
A LEADING forensic scientist this week criticised the scientific
evidence in the so-called Maguire case, in which seven people were
convicted in 1976 for running an IRA bomb factory. The surviving
defendants (one died in jail) have, since their release, sought to clear their
names . . .
The forensic tests were the main evidence against the Maguire
Seven. Government scientists told the 1976 court hearing that the seven
had been kneading the nitroglycerine [used in the bombing].
An 18-year-old trainee at the Royal Armament Research and
Development Establishment (RARDE) found sizeable amounts of the
explosive nitroglycerine in a thin-layer chromatography analysis of hand
swabs from the accused. All seven were strongly positive. No other traces
of explosives were found in the house . . .

a
b
c

Nitroglycerine forms colourless solutions. How might it be made visible in thinlayer chromatography?
In the mid 1970s, scientific policy was to use up all the sample when performing
such tests. Suggest a reason for this.
On what grounds might the forensic scientist be criticising the scientific
evidence?

A11.
a
b
c

Nitroglycerine can be seen by placing a chromatogram under an ultraviolet light


since nitroglycerine absorbs light of this energy.
If a very small amount of compound were available, all of it may need to be
analysed to provide a detectable concentration.
The relative inexperience of the person performing the analysis was criticised.
Furthermore, since the entire sample was used up in performing the test, further
confirmatory tests could not be undertaken.
A court hearing in 1991 quashed the convictions upon hearing evidence that poor
laboratory practice was involved in obtaining the forensic evidence. In particular,
it was found that some testing materials were contaminated with traces of
nitroglycerine.

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Chapter 6 Chromatography
Q12.
Refer to Figure 6.19.

Figure 6.19

b
c

The following materials are commonly used in chromatography: water, ethanol,


paraffin wax, glass sheets, paper strips, powdered alumina, nitrogen gas and
hexane.
Choose a suitable stationary phase and mobile phase from the list to use in the
analysis of amino acids by thin-layer chromatography.
Calculate the distance moved by the sample of leucine if the solvent front moves
13 cm from the origin.
The separation of taurine and glycine on the chromatogram is not very great.
State what would happen to the Rf values of the two amino acids if the separation
was carried out for a longer period so the solvent front moved 10 cm instead of
5 cm from the origin. Explain your answer.
Write a short paragraph explaining how leucine is separated from the other amino
acids.

A12.
a

Stationary phase = powdered alumina (also accept powdered alumina on glass


sheet).
Mobile phase = water or ethanol. The mobile phase should be a polar solvent in
order to dissolve the polar sample.
distance from origin by leucine
Rf leucine =
distance moved from origin by solvent
0.29 cm
Rf leucine =
= 0.58
5 cm
Rf value is same regardless of the distance travelled by solvent front
distance from origin by leucine
0.58 =
13 cm
Distance from origin by leucine = 13 cm 0.58 = 7.5 cm
The Rf values would not change. The movement of the component and solvent
front both increase by the same proportion so there is no change in the Rf.

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Chapter 6 Chromatography
d

As the mobile phase travels up the TLC plate it will absorb the amino acids and
sweep them forward over the stationary phase. The amino acids are also attracted
to the stationary phase and will tend to stick or adsorb onto it. This adsorption
and desorption process will happen many times. The amino acids have different
solubilities and adsorption strengths so they undergo this process to different
degrees, travel up the plate at different rates and separate.

Q13.
What are the advantages of HPLC for the analysis of drugs compared to an analysis
technique based on column chromatography?
A13.
Compared with conventional column chromatography, HPLC is more sensitive,
faster, resolves components better and it is able to detect colourless components
readily.
Q14.
The organophosphorus insecticide parathion has been widely used in mosquito-prone
areas. An empty drum of the insecticide was found close to a major reservoir. The
EPA was asked to analyse the water to determine whether it was a threat to human
health. Levels above 0.01 mg L1 in water are a threat to human health. Parathion has
an LD50 value (lethal dose to 50% of test animals exposed to this concentration) of
8 mg kg1.
Parathion standards in water of 0 ppm, 10 ppm, 20 ppm and 30 ppm parathion were
prepared and analysed by HPLC (Figure 6.20). An undiluted sample of the reservoir
water was run on the column under the same conditions.

Figure 6.20

Chromatograms produced for suspected contaminated water sample and parathion


standards.

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Chapter 6 Chromatography
a

Complete the table below.


Standard
Standard 0 ppm parathion
Standard 10.0 ppm parathion
Standard 20.0 ppm parathion
Standard 30.0 ppm parathion
Reservoir water

b
c
d
e
f

Peak height (cm)

Construct a calibration curve for the analysis of parathion.


Determine the concentration of parathion in the water sample. (Assume that peak
height is a measure of the concentration of the insecticide.)
Is the reservoir water within the legal limits for safe drinking? Demonstrate your
answer with a calculation.
What volume of water would a laboratory mouse, mass 150 g, need to drink to
reach the LD50 dose?
Give possible reasons to explain the small peak observed with the 0 ppm standard
of parathion.

A14.
a
Standard
Standard 0 ppm parathion
Standard 10 ppm parathion
Standard 20 ppm parathion
Standard 30 ppm parathion
Suspected contaminated water

Peak height (cm)


0.2
1.5
3.1
4.4
2.0

c
d

Concentration of parathion in water sample = 13 ppm


13 ppm 13 g/mL 13 mg/L
No, this is over 1000 times the allowable concentration.

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Chapter 6 Chromatography
e

LD50 of 8 mg/kg 8 mg/1000 g 150 g = 1.2 mg. A mouse of 150 g has a 50%
chance of being killed by a 1.2 mg dose of parathion.
1.2
Volume of water which contains 1.2 mg parathion =
L = 0.092 L = 92 mL
13
A number of reasons could account for the small peak in the 0 ppm standard.
Water used for dilution of standards or glassware may have been contaminated
with parathion.
Small quantities of parathion may be leached off the column by solvent.
Small quantities of substances with similar retention times to parathion may be
present.

Q15.
In gasliquid chromatography:
a What is the usual mobile phase?
b What is the stationary phase?
c Why is the column packed with very fine particles?
d Why is the injection port heated?
A15.
a
b
c
d

nitrogen
high boiling liquid hydrocarbon or ester
Fine particles increase the surface area, which is coated with the stationary phase.
The greater the surface area of stationary phase, the more particles that can be
adsorbed at any instant and the better the separation of components.
To turn the sample components and solvent into a gas.

Q16.
Explain how gas chromatography can be used for:
a qualitative analysis
b quantitative analysis
A16.
a

The time taken for a component to pass through the column of a GLC instrument
is called the retention time, Rt. The Rt is characteristic of the component under the
operating conditions in use and can be used to identify substances by comparing
the Rt of unknown components with those of known substances.
The relative amount of a component in a mixture may be determined by
measuring the area under the peak of the component. This area is compared with
the areas under peaks for samples containing the component in different known
concentrations.

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Chapter 6 Chromatography
Q17.
A mixture of four alkanes, decane, heptane, hexane and octane, were separated by
gasliquid chromatography. The solubility of the hydrocarbons in the liquid phase on
the column was directly proportional to the relative molecular mass of the alkane.

Figure 6.21
Chromatogram of four hydrocarbons.

a
b
c
d

Identity the hydrocarbons A, B, C and D.


Why does decreased solubility of a chemical in the stationary phase decrease the
retention time?
Why do the peaks become broader with increased retention time?
List the factors that can increase the retention time of a particular chemical in
GLC.

A17.
a
b

A = hexane (lowest relative molecular mass); B = heptane; C = octane; D =


decane (highest relative molecular mass).
A compound which is relatively insoluble in the liquid stationary phase tends to
spend little time dissolved in the liquid and therefore stationary, but is swept
along the column by the gas and reaches the detector quickly. The retention time
is therefore low.
Compounds that are relatively insoluble in the stationary phase will tend to have
all molecules swept along with very little stationary time, so retention times of
all molecules will be very similar, producing a narrow peak. More soluble
compounds will have molecules that move in and out of solution in the stationary
phase. More movements in and out of the stationary phase will increase the
retention time in the column. The longer the time on the column, the greater the
possible variation and the broader the peak.
For example, longer column, stationary phase that has greater solubility with
sample, lower the temperature, decreased flow rate of gas through column.

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Chapter 6 Chromatography
Q18.
The organic compounds dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH) have
the same molecular formula, C2H6O, and the same molar mass; however they have
different structural formulas.
A sample containing both ethanol and dimethyl ether is analysed by GLC using a
flame ionisation detector.
a Will the two compounds produce peaks with the same retention time? Explain
your answer.
b If the sample has the same concentration of both chemicals, will the peaks
produced have the same area? Explain your answer.
A18.
a
b

No. The retention time depends on solubility in the stationary phase. This
depends on the functional groups on the compounds.
No. The peak area depends on the sensitivity to the flame ionisation detector.
This depends on the structure of the molecule and the ions that are formed in the
FID cell. Consequently, if the concentration of more than one constituent of a
sample is to be determined, separate calibration curves must be used for each
compound.

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Chapter 6 Chromatography
Q19.
A herbal tea extract was analysed using HPLC. The chromatogram obtained is shown
in Figure 6.22.

Figure 6.22

a
b
c

Explain what information chemists can obtain from this chromatogram.


How many components are evident?
Briefly explain how the components are separated by the HPLC technique.

A19.
a
b
c

Chemists can determine the number of components and the absorption of


components, from which concentration can be determined.
4
Solid samples are dissolved in a suitable solvent. The liquid sample is injected
into the top of an HPLC column. The stationary and mobile phases are chosen to
achieve a good separation of the components in the sample. The sample
components alternately adsorb onto the stationary phase and then desorb into the
solvent as they are swept forward. The time taken to exit the column increases if
the component strongly absorbs onto the stationary phase and has a low solubility
in the mobile phase.

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Chapter 6 Chromatography
Q20.
Various forms of heart disease including angina are very successfully treated using
nitroglycerine patches. The small colourless plastic patches are stuck to the skin and
slowly release nitroglycerine into the blood at a rate of 0.4 mg/h. The amount of
nitroglycerine in the patches must be controlled carefully to prevent an overdose.
A nitroglycerine patch was dissolved in approximately 20 mL ethanol and then
diluted to 100 mL. 10.0 mL of this solution was diluted again to 100 mL with water.
20 L volumes of the diluted sample and 20 L of each of the prepared standards of
nitroglycerine were injected onto a 1.5 m GLC column and analysed using a nitrogenspecific detector.
Nitroglycerine standards
Standard 5 g/mL
Standard 10 g/mL
Standard 15 g/mL
Diluted sample solution
a
b
c

Peak area (mm2)


7.2
14.6
22.0
10.8

Construct a calibration curve and determine the concentration of nitroglycerine in


the diluted sample.
What mass of nitroglycerine was in the patch?
The patch has a total mass of 0.50 g. What is the percentage concentration (w/w)
of nitroglycerine in the patch?

A20.
a
b

Concentration of nitroglycerine in diluted sample = 8.0 g/mL


100 mL of diluted sample solution 8.0 g/mL 100 mL = 800 g
10 mL of stock solution contained 800 g nitroglycerine
100 mL of stock solution contained 8000 g nitroglycerine 8.0 mg
nitroglycerine
Percentage of nitroglycerine in patch = 8.0 mg/500 mg 100% = 1.6% w/w

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Chapter 6 Chromatography
Q21.
Aspirin is a drug widely used in headache and cold preparations. Organic compounds
such as aspirin in a formulation can be analysed by a variety of methods, for example
paper chromatography, thin-layer chromatography, gasliquid chromatography or
high performance liquid chromatography. Final choice of a method of analysis
involves consideration of the facilities available in the laboratory as well as problems
inherent in each technique. A range of problems that can occur with some of these
techniques is listed. Complete the table below using the letter codes to indicate the
problem or problems associated with each technique. Problems may be used more
than once.
A Difficult or impossible to get quantitative data
B Requires large amounts of solvent to operate
C Samples must be stable to heat
D Samples must be able to be dissolved in solvent
E Expensive equipment needed
F Samples cannot have a high molecular mass
Technique
Paper chromatography
Column chromatography
Thin-layer chromatography
Gasliquid chromatography
High performance liquid chromatography

Problem(s) (give letter)

A21.
Technique
Paper chromatography
Column chromatography
Thin-layer chromatography
Gasliquid chromatography
High performance liquid chromatography

Problem(s) (give letter)


A, D
A, B, D
A, D
C, D, E, F
B, D, E

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