1. Organic compounds are often identified by using more than one analytical technique.

Some of these
techniques were used to identify the compounds in the following reactions.

C3H7Br → C3H8O → C3H6O

A B C

(a) Using H2O as an example, describe what happens, at a molecular level, during the absorption
of infrared radiation.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(3)

(b) The infrared spectrum of B showed a broad absorption at 3350 cm–1. The infrared spectrum
of C did not show this absorption, but instead showed an absorption at
1720 cm–1. Explain what these results indicate about the structures of B and C.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

(c) The mass spectrum of A showed two lines of approximately equal height, one of which was
at m/z = 122. State the m/z value of the other line and explain these observations.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(3)

(d) The evidence in (b) and (c) indicates that each compound (A, B and C) could have two
possible structures. Draw the two possible structures of C.

(2)

(e) Fragmentation of C in a mass spectrometer produced lines with m/z values of 15 and 28, but
none at values of 14 or 29. Identify C and explain how you used this information to do so.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

1
 (f) State the number of lines in the 1H NMR spectrum of each of the structures in (d).

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

2. A student used the technique of ascending paper chromatography in an experiment to investigate

some permitted food dyes (labelled P1−P5). The result is shown below.

4
Distance / cm

P1 P2 P3 P4 P5
0

(a) By reference to the diagram above, describe how the experiment would be carried out and
explain the meaning of the terms stationary phase, mobile phase, partition, solvent front and
Rf value.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(8)

(b) (i) Calculate the Rf value of P1.

..........................................................................................................................

..........................................................................................................................

..........................................................................................................................
(2)

(ii) State, giving a reason, whether P4 is a single substance or a mixture.

............................................................................................................................

............................................................................................................................
(1)

2
3. Explain the following observation:

Hydrogen iodide is infrared active whereas iodine is infrared inactive.

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

4. (a) All chromatographic techniques involve the phenomena of adsorption or partition. They all
use a stationary phase and a mobile phase, but these phases can include solids, liquids or
gases. Complete the following table to show which states of matter are used in the two
phenomena.

Stationary phase Mobile phase

Adsorption
Partition
(3)

(b) Explain the term Rf value used in some chromatographic techniques.

.....................................................................................................................................

.....................................................................................................................................
(1)

(c) Outline how the technique of column chromatography could be used to separate a mixture of
two coloured substances in solution.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(4)

5. Aqueous solutions containing complexes of transition metals are usually coloured. This is due to the
absorption of part of the spectrum of white light passing through the solution.

(a) Three factors help to determine the colour absorbed.

For each of the following pairs, state the difference between the two complexes that is
responsible for the difference in colour.

[Co(NH3)6]2+ and [Ni(NH3)6]2+

.....................................................................................................................................

.....................................................................................................................................

[Fe(H2O)6]2+ and [Fe(H2O)6]2+

.....................................................................................................................................

.....................................................................................................................................

[Cu(NH3)4(H2O)2]2+ and [Cu(H2O)6]2+

.....................................................................................................................................

.....................................................................................................................................
(3)

3
 (b) The wavelength of colour absorbed by the complex can be explained in terms of the splitting
of the d orbitals in the metal ion.

The arrangement of electrons in the d orbitals of the Cu2+ ion is shown in the following
diagram.

Draw a diagram to show how the electrons are arranged in Cu2+ when it is present in the [Cu
(H2O)6]2+ ion.
(1)

(c) Predict whether the splitting of the d orbitals in [Cu(NH3)4(H2O)2]2+ and [CuCl4]2– would be
less than or greater than the splitting in [Cu(H2O)6]2+.
(1)

splitting in [Cu(NH3)4(H2O)2]2+ ...............................................................................

splitting in [CuCl4]2– ...............................................................................

(Total 5 marks)

6. The mass spectra of halogenoalkanes show more than one line corresponding to the molecular ion.
This is due to the presence of isotopes such as 35Cl, 37Cl, 79Br and 81Br.

(a) Analyse the following spectra of halogenoalkanes P and Q and deduce the formula of all the
molecular ion species.

Spectrum of P
100

80

60
Relative
abundance /
% 40

20

0
20 30 40 50 60 70
m/z

Spectrum of Q
100

80

60
Relative
abundance /
% 40

20

0
0 40 80 120 160 200
m/z
[Source: NIST Mass Spec Data Center, S E Stein, director, “IR and Mass Spectra” in NIST Chemistry WebBook,
NIST Standard Reference Database Number 69, Eds. P J Linstrom and W G Mallard, July 2001, National Institute
of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov)]

species in P ..................................................................................................................

species in Q .................................................................................................................
(3)

4
 (b) Predict the m/z values of the molecular ions for the compounds C2H5Br and C2H4Cl2

C2H5Br ......................................................................................................

C2H4Cl2 ......................................................................................................
(2)

7. This question is about the three organic compounds involved in the following reaction.

C2H4O2 + C2H6O → C4H8O2 + H2O

W X Y

(a) The infrared spectra of all three compounds showed several absorptions. Describe what
happens on a molecular level when molecules absorb infrared radiation.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(3)

(b) Use the following information about their infrared spectra to deduce which bonds are present
in the three compounds.

All three compounds showed an absorption close to 1200 cm–1.

There were broad absorptions in both W and X. The one in W was centred around 3000
cm–1, and in X around 3400 cm–1.
Compounds W and Y showed absorptions close to 1700 cm–1.

bonds in W ...........................................................................................................................

bonds in X ............................................................................................................................

bonds in Y ............................................................................................................................
(3)

(c) The 1H NMR spectra of the three compounds were available. State what can be deduced from
each of the following.

(i) The presence of two peaks in the spectrum of W.

...........................................................................................................................

...........................................................................................................................
(1)

(ii) The presence of a triplet and a quartet, with areas in the ratio 3:2, respectively, in the
spectra of both X and Y.

...........................................................................................................................

...........................................................................................................................
(1)

(d) Use your answers to (b) and (c) to deduce the structures of the three compounds.

W ...........................................................................................................................

...........................................................................................................................

X ..........................................................................................................................

...........................................................................................................................

5
 Y ..........................................................................................................................

...........................................................................................................................
(3)

(e) The infrared spectrum of compound Z, an isomer of Y, is shown below.

100

80

Transmittance / % 60

40

20

3 000 2 000 1 000

Wavenumber / cm–1

(i) Estimate the wavenumber values of the three most prominent absorptions in this
spectrum and suggest which bonds are responsible for them.

absorption 1 ............................................................................................

absorption 2 ............................................................................................

absorption 3 ............................................................................................
(3)

(ii) Deduce the structure of Z.

...........................................................................................................................

...........................................................................................................................
(1)

8. The figure below depicts the visible region of the electromagnetic spectrum and the two regions
nearest to it.
visible

A B

Increasing wavelength

(a) Name the regions labelled A and B, identify the atomic or molecular processes associated
with each region and compare the energies of the photons involved in these processes.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(5)

(b) State, giving a reason, which region (A or B) could be used to

(i) test for metal ions.

6
 ...........................................................................................................................

...........................................................................................................................
(1)

(ii) obtain information about the strengths of bonds.

...........................................................................................................................

...........................................................................................................................
(1)

9. (a) Draw structures for two possible isomers of a compound with the formula C2H4O2.

(2)

(b) The infrared spectrum of this compound shows the following absorptions: 2920, 2765 and
1710 cm–1. Use the information in Table 18 of the Data Booklet to assign each absorption to a
particular vibration.

2920 cm–1 .....................................................................................................................

......................................................................................................................................

2765 cm–1 .....................................................................................................................

......................................................................................................................................

1710 cm–1 ......................................................................................................................

......................................................................................................................................
(2)

(c) Deduce the structure from (a) which would demonstrate the infrared absorptions above.
Explain your answer.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

1
10. (a) H NMR spectroscopy can be used to obtain information about the structure of molecules.

State the information that can be obtained from the

(i) number of peaks.

...........................................................................................................................

...........................................................................................................................
(1)

(ii) chemical shift.

...........................................................................................................................

...........................................................................................................................
(1)

(iii) ratio of peak areas.

...........................................................................................................................

...........................................................................................................................
(1)

(iv) splitting pattern.

7
 ...........................................................................................................................

...........................................................................................................................
(1)

(b) The 1H NMR spectrum of a compound with the formula C4H8O2 exhibits three major peaks
with chemical shifts, areas and splitting patterns given below.

chemical shift / ppm peak area splitting pattern

0.9 3 triplet

2.0 2 quartet

4.1 3 singlet

Using information from Table 19 in the Data Booklet, determine the types of proton present
in the molecule.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(3)

(c) Deduce a structure consistent with the information indicated in (b). Explain your answer.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(5)

11. An organic compound with three carbon atoms has two structural isomers A and B with the same
functional group. The infrared spectrum of the compound shows a broad absorption at about 3350
cm–1.

(a) The mass spectra of the two isomers A and B are as follows.

100

80
Relative Intensity

60

40

20

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

8
 100

80

Relative Intensity
60

40

20

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

(i) Deduce, giving a reason, the molecular formula of the organic compound.

........................................................................................................................

........................................................................................................................
(1)

(ii) Deduce the formula of the fragmentation ion responsible for the peak at each of these
m/z values.

isomer A 29 ..........................................................................................

31 ..........................................................................................

isomer B 30 ..........................................................................................

45 ..........................................................................................
(4)

(b) The 1H NMR spectra of isomers A and B are shown below.

Isomer A

6 5 4 3 2 1 0
chemical shift  / ppm

9
 Isomer B

6 5 4 3 2 1 0
chemical shift  / ppm

(i) State the formula and function of the compound responsible for the peak at 0 ppm.

........................................................................................................................

........................................................................................................................
(2)

(ii) Explain what information about the isomers can be obtained from the number of peaks
and area under each peak.

........................................................................................................................

........................................................................................................................
(2)

(iii) Deduce the structural formulas of isomers A and B and give the ratio of peak areas in
each case.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................
(4)

(iv) Draw the structural formula of a third isomer C that has the same molecular formula as
isomers A and B but a different functional group. Give the ratio of peak areas in isomer
C.

........................................................................................................................

........................................................................................................................
(2)

12. Describe a chromatographic technique used to identify the amino acids formed when a protein is
hydrolysed.

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

13. Suggest a chromatographic technique that could be used to detect the alcohol concentration in a

10
 sample of blood. Outline the essential features of this technique.

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

14. Identify one analytical technique, different in each case, which can be used to obtain the following
information about a molecule.

Information Analytical technique

Number of different hydrogen
environments
Types of functional group

Molecular mass

15. The infrared spectra of propanoic acid and methyl ethanoate contain absorptions in characteristic
wavenumber ranges. Using Table 18 in the Data Booklet, identify:

(a) two wavenumber ranges common to both compounds.

....................................................................................................................................

....................................................................................................................................
(1)

(b) one wavenumber range found only in the spectrum of one compound.

....................................................................................................................................
(1)

16. Identify one analytical technique, different in each case, that can be used to obtain the following
information:

Information Analytical technique

Isotopic composition of an element

Functional groups present in an organic

compound
Concentration of Fe3+ ions in industrial
waste waters

17. (a) The diagram below represents the principal parts of a double beam infrared spectrometer.

A
B
S
M

D
C

(i) Name the parts labelled A, B, and C.

11
 A: ....................................................................................................................

B: ....................................................................................................................

C: ....................................................................................................................
(2)

(ii) Describe the function of the monochromator, M.

.........................................................................................................................

.........................................................................................................................
(1)

(iii) Explain how the detector, D, works.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(2)

(b) State and explain what happens to a molecule when it absorbs infrared radiation.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(2)

18. (a) Each of the infrared absorptions A, B and C is produced by one of the compounds I, II and
III. Deduce which compound is responsible for each absorption, and identify the bond
causing the absorption.

I II III
NH 2
OH
H CH 2
C C
CH3 H

wavenumbers in cm–1

3500 3300 3100 1800 1700 1600 1800 1700 1600

A B C

Absorption Compound Bond

A
B
C
(5)

12
 (b) Identify which of the absorptions, A, B or C, indicates the greatest amount of energy, giving
a reason for you choice.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

19. (a) Chromatography is usually coupled with another analytical technique. Identify the analytical
technique that is most commonly coupled with gas-liquid chromatography (GLC).

....................................................................................................................................

....................................................................................................................................
(1)

(b) Chromatographic techniques include the following.

LC (column chromatography)
GLC (gas-liquid chromatography)
HPLC (high performance liquid chromatography)

(i) Explain why LC is used in preference to GLC or HPLC to separate a pharmaceutical

drug from its production batch.

.........................................................................................................................

.........................................................................................................................
(1)

(ii) Identify, giving a reason, which of the techniques GLC or HPLC is more suitable for
determining the composition of a mixture of sugars.

.........................................................................................................................

.........................................................................................................................
(2)

(c) Two samples of unknown alkaloids (X and Y) are analysed using paper chromatography.
They are compared against the results obtained with samples of four known alkaloids A, B, C
and D. The results are shown in the table below:

A B C D X Y

Sample Rf value
A 0.1
B 0.5
C 0.7
D 0.8
X 0.1 and 0.3
Y 0.5

(i) Explain how an Rf value is calculated.

13
 .........................................................................................................................

.........................................................................................................................
(1)

(ii) Use the results above to discuss the composition of samples X and Y.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(3)

20. An organic compound X contains 48.6 of carbon, 8.2 of hydrogen and 43.2 of oxygen by
mass. The mass spectrum and infrared spectrum of this compound are as follows:

Mass spectrum of compound X

100 74
29
Relative abundance

45
50

57

20 40 60 80
m/z

Infared spectrum of compound X

Transmittance

A C
B
4000 3000 2000 1600 1200 800
wavenumber/cm –1

(a) Calculate the empirical formula of this compound.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(1)

(b) Deduce, stating a reason for your answer, the molecular formula of this compound.

....................................................................................................................................

....................................................................................................................................
(1)

(c) Suggest the formula of the fragmentation ion that could be responsible for the peak at each of
the following m/z values.

57 ...............................................................................................................................

14
 45 ...............................................................................................................................

29 ...............................................................................................................................
(3)

(d) Identify the bond responsible for each of the absorptions labelled A, B and C.

A ...............................................................................................................................

B ...............................................................................................................................

C ...............................................................................................................................
(2)

(e) The compound X exists as three structural isomers. An 1H NMR spectrum was obtained for
each isomer. Draw the structural formula of the three isomers and deduce the splitting
pattern in each case.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(6)

(f) Suggest with a reason the identity of compound X.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(2)

21. (a) Electronic transitions occur when a molecule absorbs energy from the visible or UV regions
of the electromagnetic spectrum.

(i) Predict the region (visible or UV) in which benzene and nitrobenzene would absorb
energy.

.........................................................................................................................

.........................................................................................................................

...............................................................................................................................
(2)

(ii) Explain why CH2=CH–CH=CH2 shows an absorption band at a longer wavelength

than CH2=CH2.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(2)

(iii) Explain why compounds of Zn2+ and Cu+ are colourless.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(2)

15
 (b) An aqueous solution of copper(II) sulfate is light blue, but when excess ammonia is added the
colour changes to dark blue.

(i) State the formula of the copper(II) complex ions in each of the two solutions.

.........................................................................................................................

.........................................................................................................................
(2)

(ii) Explain why the colour of copper complex solutions is different when different ligands
are present.

.........................................................................................................................

.....................................................................................................................

.........................................................................................................................
(2)

22. Compound A, with the molecular formula C3H6O has this infrared spectrum.

Wavenumbers (cm–1)

(a) (i) Use Table 18 in the Data Booklet to list four classes of compounds that have
absorptions near 1700 cm–1.

.........................................................................................................................

.........................................................................................................................
(1)

(ii) Identify which of the classes listed in part (a)(i) could not have the molecular formula
C3H6O.

.........................................................................................................................

.........................................................................................................................
(1)

(b) The mass spectrum of compound A has prominent peaks at m/z = 15 and 29.

(i) Deduce the formula of the species responsible for each peak.

m/z = 15 ..........................................................................................................

m/z = 29 ..........................................................................................................
(2)

(ii) Deduce the structure of compound A.

16
 .........................................................................................................................
(1)

23. (i) Explain, with reference to the d orbitals in a transition metal, why complex ions are coloured.

...................................................................................................................................

...................................................................................................................................

...................................................................................................................................

...................................................................................................................................
(3)

(ii) Outline why different ligands produce different colours with the same transition metal.

...................................................................................................................................

...................................................................................................................................
(2)

24. The structures of four hydrocarbons are shown below.

I II III IV

(i) Identify the compounds that most strongly absorb ultraviolet radiation.

...................................................................................................................................
(1)

(ii) Identify the compound that absorbs ultraviolet radiation of the longest wavelength, and
explain your choice.

...................................................................................................................................

...................................................................................................................................

...................................................................................................................................

...................................................................................................................................
(2)

25. (a) Describe what occurs at a molecular level when molecules such as carbon dioxide absorb
infrared radiation.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(2)

(b) Spectra A and B (see below), represent the infrared spectra of two of these compounds:

CH3CH2COOH CH3COOCH3 HCOOCH2CH3

(i) Use Table 18 in the Data Booklet to identify the groups responsible for the absorption
near

1050 cm1 .....................................................................................................

1750 cm1 .....................................................................................................

(1)

(ii) Deduce which one of the three compounds produced spectrum A, giving a reason for

17
 your choice.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(2)

(iii) Explain why the other two compounds have similar infrared spectra.

.........................................................................................................................

.........................................................................................................................

(1)

(c) Figures C and D represent the splitting patterns and the chemical shifts shown in the 1H
NMR spectra of the same two compounds used to obtain spectra A and B.

18
 Figure C

12 10 8 6 4 2 0
Chemical shift / ppm

Figure D

12 10 8 6 4 2 0
Chemical shift / ppm

(i) State what general information can be deduced from the three different types of
splitting patterns in these spectra.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(3)

(ii) Explain how the chemical shift values close to  4.1 in figure C and close to  11.5 in
figure D can be used to identify the two compounds. Refer to information from Table
19 in the Data Booklet in answering this part.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(2)

26. Paper chromatography and column chromatography can be used as examples to explain the
difference between adsorption and partition. For each of these chromatographic techniques, identify

 the stationary and mobile phases

 how the mobile phase moves.

Identify, with a reason, which of the two techniques is more suitable for collecting samples of a
mixture for further analysis.

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................
(Total 5 marks)

27. There are four structural isomers that are alcohols with the formula C4H9OH.

(a) Explain why the infrared spectra of all four alcohols show very similar absorptions around
3350 cm–1 and 2900 cm–1.

....................................................................................................................................

19
 ....................................................................................................................................

....................................................................................................................................
(2)

(b) Describe how these alcohols can be distinguished using their infrared spectra.

....................................................................................................................................

....................................................................................................................................
(1)

(c) Explain why the mass spectra of all four alcohols show a peak at m/z = 74.

....................................................................................................................................

....................................................................................................................................
(1)

(d) Suggest the formulas of the fragments formed from C4H9OH with the following m/z values:

m/z = 57 ......................................................................................................................

m/z = 45 ......................................................................................................................
(2)

(e) The numbers of peaks, and the areas under them, in the 1H NMR spectra of these alcohols
can be used to identify them.

(i) Explain why the 1H NMR spectrum of (CH3)2CHCH2OH has four peaks. Predict the
ratio of the areas under the peaks.

.........................................................................................................................

.........................................................................................................................
(2)

(ii) Deduce the structure of the alcohol whose 1H NMR spectrum has two peaks with areas
in the ratio 9:1.

.........................................................................................................................

.........................................................................................................................

.........................................................................................................................
(1)

28. Identify two effects of the absorption of infrared radiation on the bonds in a molecule of carbon
dioxide.
Explain why an oxygen molecule does not absorb infrared radiation.

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................
(Total 3 marks)

29. Nuclear magnetic resonance spectroscopy (1H NMR) can be used to identify organic compounds.

(a) Several features of 1H NMR spectra are helpful in obtaining information about the structure
of a molecule. Outline what can be learned from each of the following:

 the number of peaks in the spectrum

 the ratio of areas under each peak
 chemical shift values () of 1.3 and 9.7 ppm

....................................................................................................................................

....................................................................................................................................

20
 ....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(4)

(b) There are four esters with the molecular formula C4H8O2. Two of them are shown below.

ethyl ethanoate CH3–COO–CH2–CH3

methyl propanoate CH3–CH2–COO–CH3

The 1H NMR spectra of these two esters, not necessarily in the correct order, are given
below.

Spectrum 1

6 5 4 3 2 1 0
Chemical shift / ppm

Spectrum 2

6 5 4 3 2 1 0

Chemical shift / ppm

(i) State and explain, in terms of the structures of both esters, the origin of the triplet and
the quartet.

..........................................................................................................................

..........................................................................................................................

..........................................................................................................................
(3)

(ii) Identify the origin of the singlet peak for either ester, and explain why this peak is not
split.

..........................................................................................................................

..........................................................................................................................

..........................................................................................................................
(2)

(iii) By referring to the singlet peak, and using information from Table 19 of the Data
Booklet, deduce which spectrum corresponds to which ester, giving a reason for your
choice in each case.

ethyl ethanoate .................................................................................................

21
 ..........................................................................................................................

..........................................................................................................................

methyl propanoate ...........................................................................................

..........................................................................................................................

..........................................................................................................................
(3)

(c) Another ester with the formula C4H8O2 has the structure.

H COO CH CH

CH 3

Predict the number of peaks, and the ratio of the areas under the peaks, in its 1H NMR
spectrum.

number of peaks ........................................................................................................

ratio of areas ..............................................................................................................

(2)

30. (a) (i) Explain why the mass spectrum of 2-chloro-2-methylpropane shows molecular ion
peaks at m/z values of 92 and 94 in the ratio 3:1.

..........................................................................................................................

..........................................................................................................................

..........................................................................................................................

..........................................................................................................................
(2)

(ii) Suggest the formulas of the species with the following m/z values in this spectrum:

m/z = 77

m/z = 57
(2)

(b) Predict the m/z values of the three main molecular ion peaks in dichloromethane.

....................................................................................................................................

....................................................................................................................................
(2)

31. Compounds A and B are alcohols with the molecular formula C3H8O. The following information
was obtained from a mass spectrum of each alcohol.

A: peaks at m/z = 29, 31, 60

B: peaks at m/z = 45, 60

(a) Deduce the formula of the species responsible for the peak at m/z = 60.

.....................................................................................................................................
(1)

(b) Deduce the formula of the species with m/z = 31.

.....................................................................................................................................
(1)

(c) Deduce the structure of each alcohol.

Structure of A Structure of B

(2)

22
32. The figure below shows the visible region of the electromagnetic spectrum and the two regions
nearest to it.

visible
A B

increasing wavelength

(a) Name the regions labelled A and B, identify the atomic or molecular processes associated
with each region and compare the energies of the radiation involved in these processes

Region A ....................................................................................................................

.....................................................................................................................................

Region B ....................................................................................................................

.....................................................................................................................................
(5)

(b) State, giving a reason, which region (A or B) could be used to test for metal ions.

.....................................................................................................................................

.....................................................................................................................................
(1)

33. (a) State the main use of atomic absorption spectroscopy (AAS).

.....................................................................................................................................

.....................................................................................................................................
(1)

(b) Ore samples may be analysed for iron using AAS. An ore sample was prepared in acid and
diluted to 1 part in 10. The diluted solution gave an absorbance reading of 0.80. Determine
the concentration of iron in the sample in mg cm–3.

1.20

1.00

0.80
Absorption

0.60

0.40

0.20

0.00
0 50 100 150 200
–3
Concentration / g cm

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(2)

(c) Describe the use of each of the following components of the AA spectrophotometer.

Atomizer ......................................................................................................................

.....................................................................................................................................

Monochromatic light source .......................................................................................

.....................................................................................................................................
(2)

23
34. The colours of transition metal complexes depend on several factors.

(a) Use [Mn(H2O)6]2+ and [Fe(H2O)6]2+ as examples to outline why the colours depend on the
identity of the transition metal.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(3)

(b) Outline why the colour depends on the oxidation state of the transition metal.

.....................................................................................................................................

.....................................................................................................................................
(1)

35. An analgesic tablet contains 400 mg of aspirin and 80 mg of caffeine. The molecular formula of
aspirin is C9H8O4 and that of caffeine is C9H10N4O2.

(a) State and explain which method, gas-liquid chromatography (GLC) or high performance
liquid chromatography (HPLC), would be best for the separation and mass determination of
aspirin and caffeine in the tablet.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(2)

(b) State and explain which of the two components would have the shorter retention time.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(2)

(c) Sketch a chromatograph for the separation of the aspirin and caffeine in the analgesic tablet.

time
(2)

24