HKDSE CHEMISTRY — A Modern View (Second Edition)

Part XV Analytical chemistry

Chemistry: Chapter 64 Instrumental analytical methods

Structured questions

Sections 64.164.2
|!|CMELH0156400001|!|
The concentration of copper(II) sulphate solution can be determined by colorimetry. A
set of standard copper(II) sulphate solutions was used to construct a calibration curve.
The absorbances of the copper(II) sulphate solutions were recorded as follows:

Concentration of CuSO4(aq) (mg dm3) Absorbance

0 0.000
0.125 0.120
0.250 0.250
0.500 0.510
0.750 0.770

(a) Using the data in the above table, plot a calibration curve of copper(II) sulphate
solutions. (2 marks)

(b) What would be the concentration of copper(II) sulphate solution if it had an

absorbance of 0.400? (1 mark)

(c) Besides colorimetry, precipitation titration can also be used to determine the
concentration of copper(II) sulphate solution.

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(i) Suggest a titrant for the titration. (1 mark)

(ii) Write an ionic equation for the reaction involved. (1 mark)

(iii) State the dependent variables of the titration. (1 mark)

##
(a)
Absorbance

Concentration of CuSO4(aq) (mg dm3)

Correct graph 1
Correct labelling of axes 1
(b) 0.390 mg dm3 1
(c) (i) Sodium hydroxide solution (accept other reasonable answers) 1
(ii) Cu2+(aq) + 2OH(aq)  Cu(OH)2(aq) 1
(iii) The conductivity of the reaction mixture 1
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##

|!|CMELH0156400002|!|

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Sunset yellow is a food dye commonly added to soft drinks. It may cause
hyperactivity in children. You were asked to determine the concentration of sunset
yellow in a brand of soft drink. A set of standard sunset yellow solutions was used to
construct a calibration curve. The absorbance values of different concentrations of
sunset yellow solutions were recorded as follows:

Concentration of sunset yellow solution (mg dm3) Absorbance

0.0 0.000
0.4 0.186
0.8 0.358
1.2 0.537
1.6 0.710
2.0 0.897

(a) Using the data in the table, plot a calibration curve of sunset yellow solutions.
(2 marks)

(b) If a 25 cm3 of test sample from the soft drink has an absorbance of 0.790, what is
its sunset yellow concentration? (1 mark)

(c) European food safety authority suggests that the maximum acceptable daily
intake of sunset yellow should be 1.0 mg per kg of bodyweight. Based on this

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

standard, is it safe for a 23.0 kg child to drink a can of the soft drink (375 ml) per
day? Explain your answer with calculation. (3 marks)

##
(a)
Absorbance

Concentration of sunset yellow solutions (mg dm3)

Correct graph 1
Correct labelling of axes 1
(b) 1.78 mg dm3 1
(c) The maximum acceptable daily intake of sunset yellow for a 23.0 kg
child = 1.0 mg kg1 × 23.0 kg = 23.0 mg 1

Mass of sunset yellow in a can of soft drink = 1.78 mg × = 0.668

mg 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

As the mass of sunset yellow in a can of soft drink is much lower than the
maximum acceptable daily intake, it is safe for a 23.0 kg child to drink a
can of soft drink per day. 1
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##

|!|CMELF0156400003|!|
Riboflavin is known as vitamin B2. It dissolves in water to form a yellow solution. A
set of standard riboflavin solutions was used to construct a calibration curve. The
absorbance values were recorded as follows:

Concentration of riboflavin ( × 105 M) Absorbance

0 0.000
1.0 0.200
2.1 0.400
3.1 0.600
4.3 0.800
5.4 1.000

(a) What is the relationship between the colour intensity of the riboflavin solution
and the absorbance? (1 mark)

(b) Name an instrument that can be used to determine the absorbance of riboflavin
solution. (1 mark)

(c) Using the data in the above table, plot a calibration curve of riboflavin solutions.
(2 marks)

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Part XV Analytical chemistry

(d) What would be the concentration of the riboflavin solution if it had an

absorbance of 0.680? (1 mark)

##
(a) The absorbance of the riboflavin solution is directly proportional to the
colour intensity of the solution. 1
(b) Colorimeter 1
(c)
Absorbance

Concentration of riboflavin (× 105 M)

Correct graph 1
Correct labelling of axes 1
(d) 3.7 × 105 M 1
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##

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Section 64.3
|!|CMELF0156400004|!|
Ethanol is manufactured by reacting ethene with steam.
CH2=CH2(g) + H2O(g) CH3CH2OH(g)
The reaction mixture is analysed by an infrared spectrophotometer.

(a) By interpreting the infrared spectrum, what information from the spectrum shows
that the reaction is completed? (2 marks)

(b) If ethanol is exposed to air for a long time, it smells sour.

(i) Identify the compound that contributes to the sour smell. (1 mark)

(ii) If the compound is analysed by an infrared spectrophotometer, which two

characteristic peaks would you expect to observe in the infrared spectrum?
Explain why. (2 marks)

##
(a) If ethene is present, an absorption peak between 16101680 cm1 should
be observed. 1
1
The absence of the absorption peak between 16101680 cm indicates
that all ethene has been converted to ethanol. 1
(b) (i) Ethanoic acid 1
(ii) A strong and broad absorption peak between 25003300 cm1 would
be observed because of the absorption of OH bond in ethanoic acid. 1
A strong absorption peak between 16801800 cm1 would be
observed because of the absorption of C=O bond in ethanoic acid. 1
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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

|!|CMELF0156400005|!|
Aspirin is a painkiller. It is used to relieve pains and fever.

(a) Write the structural formula of aspirin. (1 mark)

(b) Suggest a chemical test to show the presence of carboxyl group in aspirin.
(2 marks)

(c) The IR spectrum of aspirin is shown below:

Transmittance (%)

Wavenumber (cm1)

(i) Identify TWO absorption peaks corresponding to the absorption of the

bonds in carboxyl group. (2 marks)

(ii) Explain why it is NOT possible to deduce the structure of aspirin by

interpreting IR spectrum only. (1 mark)

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Part XV Analytical chemistry

##
(a)

1
(b) Add aspirin to sodium carbonate solution. 1
Colourless gas bubbles will be given out. 1
(c) (i) A strong absorption peak at around 1700 cm1 is due to the
absorption of C=O bond in carboxyl group. 1
A broad absorption peak at around 3000 cm 1 is due to the
absorption of OH bond in carboxyl group. 1
(ii) IR spectrum can only give the information about the functional
groups in aspirin. 1
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##

|!|CMELF0156400006|!|
An unknown compound A can turn acidified potassium dichromate solution from
orange to green. It has the following composition by mass: 60.0% carbon, 13.3%
hydrogen and 26.7% oxygen.

(a) Determine the empirical formula of A.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(b) If the molecular mass of A is 60.0, determine its molecular formula. (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(c) (i) Write TWO possible structural formulae of A. (2 marks)

(ii) Which type of isomers are they? (1 mark)

(d) State ONE characteristic absorption band that could be observed in the IR
spectrum of A. Explain why. (2 marks)

##
(a) Assume that there are 100 g of A.
C H O
Mass (g) 60.0 13.3 26.7
Number of
= 5.0 = 13.3 = 1.67
moles (mol)
Mole ratio
=3 =8 =1

1
∴ empirical formula of A is C3H8O. 1
(b) Let the molecular formula of A be (C3H8O)n.
n × (12.0 × 3 + 1.0 × 8 + 16.0) = 60.0
n=1
∴ molecular formula of A is C3H8O. 1
(c) (i)

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Part XV Analytical chemistry

1
(ii) They are position isomers. 1
(d) A strong and broad band at about 32303670 cm1 can be observed 1
because of the absorption of OH bond in alcohols. 1
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##

|!|CMELF0156400007|!|
Compound X, with a relative molecular mass of 60.0, has the following composition
by mass:
C: 60.0%, H: 13.3%, O: 26.7%
The infrared spectrum of compound X is shown below.
Transmittance (%)

Wavenumber (cm1)

Compound X reacts with acidified potassium dichromate solution to give compound

Y. When compound Y is tested with Tollens’ reagent, there is no observable change.

(a) Determine the molecular formula of compound X.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (3 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(b) Based on the infrared spectrum only, write TWO possible structural formulae for
compound X. (2 marks)

(c) By using the information above, determine what compound X is. (2 marks)

(d) Name compound Y. (1 mark)

##
(a) Assume that there are 100 g of compound X.
C H O
Mass (g) 60.0 13.3 26.7
Number of
= 5.0 = 13.3 = 1.67
moles (mol)
Mole ratio
=3 =8 =1

1
∴ empirical formula of X is C3H8O. 1
Let the molecular formula of X be (C3H8O)n.
n × (12.0 × 3 + 1.0 × 8 + 16.0) = 60.0
n=1
∴ molecular formula of X is C3H8O. 1
(b)

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1
(c) As compound Y does not react with Tollens’ reagent, it is a ketone. 1
Hence, compound X should be propan-2-ol. 1
(d) Propanone 1
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##

|!|CMELH0156400008|!|
Compound X is found to contain 73.4% carbon, 10.3% hydrogen and 16.3% oxygen
by mass. The relative molecular mass of X is between 90 and 100. The infrared
spectrum of X is shown below:
Transmittance (%)

Wavenumber (cm1)

X neither reacts with acidified potassium dichromate solution nor bromine (dissolved
in an organic solvent) in the dark.

(a) Determine the molecular formula of X.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (3 marks)

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Part XV Analytical chemistry

(b) From the infrared spectrum, suggest ONE functional group present in X. (1 mark)

(c) Deduce one possible structure for X. (3 marks)

##
(a) Assume that there are 100 g of X.
C H O
Mass (g) 73.4 10.3 16.3
Number of
= 6.12 = 10.3 = 1.02
moles (mol)
Mole ratio
=6 = 10 =1

1
∴ empirical formula of X is C6H10O. 1
Let the molecular formula of X be (C6H10O)n.
90 < n × (12.0 × 6 + 1.0 × 10 + 16.0) < 100

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n=1
∴ molecular formula of X is C6H10O. 1
(b) From the IR spectrum, the absorption peak at around 1700 cm1
corresponds to the presence of a C=O bond. X contains a C=O group. 1
(c) As X does not react with bromine (dissolved in an organic solvent) in the
dark, X does not contain any C=C or C≡C group. 1
As X does not react with acidified potassium dichromate solution, X is
not an aldehyde. 1
Possible structure of X is:

1
(Accept other reasonable answers) ___
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##

Sections 64.464.5
|!|CMELF0156400009|!|
Compound Y is a straight-chain carbon compound. The relative molecular mass of Y
is 100. It reacts with Tollens’ reagent to give a silver mirror. Y has the following
composition by mass: 72.0% carbon, 12.0% hydrogen and 16.0% oxygen. The
following diagram shows the mass spectrum of Y.
Relative intensity (%)

m/e

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(a) Determine the molecular formula of Y.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (3 marks)

(b) From the chemical test, deduce the homologous series that Y belongs to. (1 mark)

(c) Suggest one chemical species corresponding to the peak at m/e = 29. (1 mark)

(d) Hence, write the structural formula of Y. (1 mark)

##
(a) Assume that there are 100 g of Y.
C H O
Mass (g) 72.0 12.0 16.0
Number of
= 6.0 = 12.0 = 1.0
moles (mol)
Mole ratio
=6 = 12 =1

1
∴ empirical formula of Y is C6H12O. 1
Let the molecular formula of Y be (C6H12O)n.
n × (12.0 × 6 + 1.0 × 12 + 16.0) = 100

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n=1
∴ molecular formula of Y is C6H12O. 1
(b) Aldehyde 1
(c) The peak at m/e = 29 is due to the ion HCO+ or CH3CH2+. 1
(d)

1
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##

|!|CMELF0156400010|!|
An unknown compound Z has the following composition by mass:
C: 37.5%, H: 7.80%, Cl: 54.7%
The relative molecular mass of Z is 64.5. The mass spectrum of Z is shown below:
Relative intensity (%)

m/e

(a) Determine the molecular formula of Z.

(Relative atomic masses: H = 1.0, C = 12.0, Cl = 35.5) (3 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
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(b) Suggest one chemical species corresponding to the peaks at m/e = 66 and m/e =
49 respectively. (2 marks)

(c) Z reacts with sodium hydroxide solution to form compound W.

(i) Identify compound W. (1 mark)

(ii) State ONE characteristic absorption peak that is observed in the IR

spectrum of compound W. Explain why. (2 marks)

##
(a) Assume that there are 100 g of Z.
C H Cl
Mass (g) 37.5 7.80 54.7
Number of
= 3.13 = 7.80 = 1.54
moles (mol)
Mole ratio
=2 =5 =1

1
∴ empirical formula of Z is C2H5Cl. 1
Let the molecular formula of Z be (C2H5Cl)n.
n × (12.0 × 2 + 1.0 × 5 + 35.5) = 64.5
n=1
∴ molecular formula of Z is C2H5Cl. 1
(b) The peak at m/e = 66 is due to the molecular ion CH3CH237Cl+. 1
The peak at m/e = 49 is due to the ion CH235Cl+. 1
(c) (i) Ethanol 1

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Part XV Analytical chemistry

(ii) A strong and broad absorption band at 32303670 cm1 can be

observed 1
because of the absorption of OH bond in ethanol. 1
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##

|!|CMELF0156400011|!|
An ester is prepared by heating a mixture of propan-1-ol and propanoic acid under
reflux. Concentrated sulphuric acid is used as catalyst.

(a) Write the systematic name of the ester formed. (1 mark)

(b) The ester is then extracted from the reaction mixture. The ester is then analysed
by using infrared spectrophotometer and mass spectrometer. The infrared
spectrum and mass spectrum of the ester are shown below.
IR spectrum
Transmittance (%)

Wavenumber (cm1)

Mass spectrum

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Relative intensity (%)

m/e

(i) Identify ONE absorption peak corresponding to the absorption of C=O

bonds in ester group. (1 mark)

(ii) Suggest why the molecular ion peak is absent in the mass spectrum. (1
mark)

(iii) Suggest one chemical species corresponding to the peaks at m/e = 57 and
m/e = 29 respectively. (2 marks)

##
(a) Propyl propanoate 1
(b) (i) A strong absorption peak at around 1750 cm1 is due to the
absorption of C=O bonds in ester group. 1
(ii) The molecular ion is very unstable and it breaks down to smaller
fragment ions. 1
(iii) The peak at m/e = 57 is due to the ion CH3CH2CO+. 1
The peak at m/e = 29 is due to the ion CH3CH2+. 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

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|!|CMELH0156400012|!|
The molecular formula of compound X is C4H10O. It can be oxidized to a ketone when
added to acidified potassium dichromate solution. The mass spectrum of X is shown
below.
Relative intensity (%)

m/e

(a) Suggest the homologous series that X belongs to. Explain your answer. (2 marks)

(b) Suggest one chemical species corresponding to the peaks at m/e = 45 and m/e =
59 respectively. (2 marks)

(c) Deduce the possible structure of X. (1 mark)

(d) (i) Which type of isomerism does X exhibit? (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(ii) Is it possible to distinguish between the pair of isomers of X by mass

spectrometry? Explain briefly. (1 mark)

##
(a) X is an oxygen-containing compound. It could be an alcohol, an aldehyde
or a ketone. 1
As it can be oxidized to a ketone, X is a secondary alcohol. 1
(b) The peak at m/e = 45 is due to the ion CH3CH(OH)+. 1
The peak at m/e = 59 is due to the ion CH3CH(OH)CH2+. 1
(c) CH3CH(OH)CH2CH3 1
(d) (i) Enantiomerism 1
(ii) It is not possible as they produce the same fragmentation pattern. 1
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##

|!|CMELH0156400013|!|
Compound X is synthesized from an alcohol and a carboxylic acid. An experiment to
synthesize X involves the following steps:
Step 1: Add the alcohol, the carboxylic acid and a few drops of concentrated
sulphuric acid in a pear-shaped flask.
Step 2: Heat the reaction mixture under reflux for 30 minutes.
Step 3: Distil the reaction mixture at around 57C.
Step 4: Add excess sodium carbonate solution to the distillate.
Step 5: Add anhydrous calcium chloride to the distillate.
Step 6: Filter the calcium chloride out.

(a) Suggest the functional group present in X. (1 mark)

(b) (i) What is the purpose of adding anhydrous calcium chloride in Step 5?
(1 mark)

(ii) How do you know anhydrous calcium chloride has been added in excess?
(1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(c) The elemental analysis of X gives the following data:

Carbon: 48.7%
Hydrogen: 8.1%
Oxygen: 43.2%

(i) Determine the empirical formula of X.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(ii) The mass spectrum of X is shown below:

Relative intensity (%)

m/e

Determine the molecular formula of X. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(d) Using the information above, deduce the structural formula of X. (3 marks)

##
(a) Ester 1
(b) (i) To absorb traces of water in the distillate. 1
(ii) When anhydrous calcium chloride has been added in excess, some
of it sinks to the bottom of the flask. 1
(c) (i) Assume that there are 100 g of X.
C H O
Mass (g) 48.7 8.1 43.2
Number of
= 4.06 = 8.1 = 2.7
moles (mol)
Mole ratio
= 1.5 =3 =1

1
∴ empirical formula of X is C3H6O2. 1
(ii) From the mass spectrum, the molecular ion peak is at m/e = 74.
∴ molecular mass of X is 74. 1
Let the molecular formula of X be (C3H6O2)n.
n × (12.0 × 3 + 1.0 × 6 + 16.0 × 2) = 74
n=1
∴ molecular formula of X is C3H6O2. 1
(d) The peak at m/e = 59 is due to the ion CH3COO+. 1

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Part XV Analytical chemistry

The peak at m/e = 43 is due to the ion CH3CO+. 1

∴ X is . 1
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##

|!|CMELF0156400014|!|
Pentan-3-one and methylbutanone have the same molecular formula. The mass
spectrum below belongs to either pentan-3-one or methylbutanone.
Relative intensity (%)

m/e

(a) State the type of isomerism between pentan-3-one and methylbutanone. (1 mark)

(b) Explain why the two isomers cannot be distinguished by using 2,4-
dinitrophenylhydrazine solution. (1 mark)

(c) Identify the value of m/e for the molecular ion. (1 mark)

(d) Which isomer has the above mass spectrum? Explain your answer. (2 marks)

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Part XV Analytical chemistry

##
(a) Chain isomerism 1
(b) They both react with 2,4-dinitrophenylhydrazine to form an orange-
yellow precipitate. 1
(c) m/e = 86 1
(d) The mass spectrum belongs to methylbutanone. 1
The peak at m/e = 43 is due to the ion CH3CO+. 1
___
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##

|!|CMELF0156400015|!|
An unknown compound Y has the following composition by mass:
C: 54.5%, H: 9.1%, O: 36.4%
The infrared and mass spectra of X are shown below.
IR spectrum
Transmittance (%)

Wavenumber (cm1)

Mass spectrum

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Relative intensity (%)

m/e

(a) Determine the empirical formula of Y.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(b) By analysing the mass spectrum, determine the relative molecular mass of Y.
(1 mark)

(c) From the infrared spectrum, suggest ONE functional group present in Y. (1 mark)

(d) By analysing both the mass and infrared spectra, identify Y. (4 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

##
(a) Assume that there are 100 g of Y.
C H O
Mass (g) 54.5 9.1 36.4
Number of
= 4.54 = 9.10 = 2.28
moles (mol)
Mole ratio
=2 =4 =1

1
∴ empirical formula of Y is C2H4O. 1
(b) From the mass spectrum, the peak at m/e = 88 corresponds to the
molecular ion of Y. Therefore, the relative molecular mass of Y is 88. 1
(c) From the IR spectrum, the absorption peak at around 1750 cm1
corresponds to the presence of a C=O bond. Y contains a C=O group. 1
(d) Let the molecular formula of Y be (C2H4O)n.
n × (12.0 × 2 + 1.0 × 4 + 16.0) = 88
n=2
∴ molecular formula of Y is C4H8O2. 1
The peaks at m/e = 45 corresponds to CH3CH2O+. 1
The peaks at m/e = 43 corresponds to CH3CO+. 1
Y is ethyl ethanoate. 1
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##

|!|CMELF0156400016|!|
Compound Z is an aromatic compound. It has the following composition by mass:
C: 81.1%, H: 8.1%, O: 10.8%
The infrared and mass spectra of Z are shown below.
IR spectrum

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Part XV Analytical chemistry

Transmittance (%)

Wavenumber (cm1)

Mass spectrum
Relative intensity (%)

m/e

(a) Determine the empirical formula of Z.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(b) By analysing the mass spectrum, determine the relative molecular mass of Z.
(1 mark)

(c) By analysing both the mass and infrared spectra, deduce the possible structure of
Z. (5 marks)

##
(a) Assume that there are 100 g of Z.
C H O
Mass (g) 81.1 8.1 10.8
Number of
= 6.76 = 8.10 = 0.68
moles (mol)
Mole ratio
= 10 = 12 =1

1
∴ empirical formula of Z is C10H12O. 1
(b) From the mass spectrum, the peak at m/e = 148 corresponds to the
molecular ion of Z. Therefore, the relative molecular mass of Z is 148. 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

(c) Let the molecular formula of Z be (C10H12O)n.

n × (12.0 × 10 + 1.0 × 12 + 16.0) = 148
n=1
∴ molecular formula of Z is C10H12O. 1
From the IR spectrum, the absorption peak at around 1720 cm1
corresponds to the presence of a C=O bond. Z contains a C=O group. 1
From the mass spectrum, the peak at m/e = 105 corresponds to
C6H5CH2CH2+. 1
The peaks at m/e = 43 corresponds to CH3CO+. 1

∴ Z is . 1
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##

|!|CMELF0156400017|!|
Compound A is an aliphatic compound. It has the following composition by mass:
C: 69.8%, H: 11.6%, O: 18.6%
The infrared and mass spectra of A are shown below.
IR spectrum
Transmittance (%)

Wavenumber (cm1)

Mass spectrum

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Relative intensity (%)

m/e

(a) Determine the empirical formula of A.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(b) By analysing the mass spectrum, determine the relative molecular mass of A.
(1 mark)

(c) By analysing both the mass and infrared spectra, identify A. (5 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

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(a) Assume that there are 100 g of A.
C H O
Mass (g) 69.8 11.6 18.6
Number of
= 5.82 = 11.6 = 1.16
moles (mol)
Mole ratio
=5 = 10 =1

1
∴ empirical formula of A is C5H10O. 1
(b) From the mass spectrum, the peak at m/e = 86 corresponds to the
molecular ion of A. Therefore, the relative molecular mass of A is 86. 1
(c) Let the molecular formula of A be (C5H10O)n.
n × (12.0 × 5 + 1.0 × 10 + 16.0) = 86
n=1
∴ molecular formula of A is C5H10O. 1
From the IR spectrum, the absorption peak at around 1720 cm1
corresponds to the presence of a C=O bond. A contains a C=O group. 1
From the mass spectrum, the peak at m/e = 71 corresponds to
CH3CH2CH2CO+. 1
The peaks at m/e = 43 corresponds to CH3CO+. 1
∴ A is pentan-2-one. 1
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|!|CMELH0156400018|!|
Compound A contains carbon, hydrogen and oxygen only. The following are the
analytical results of A:
(1) The complete combustion of 0.480 g of A produces 657 cm3 of carbon dioxide
and 492 cm3 of water vapour at room temperature and pressure.
(2) A reacts with 2,4-dinitrophenylhydrazine to form an orange-yellow precipitate.
(3) A has no reaction with Tollens’ reagent.
(4) The molecular ion peak in the mass spectrum of A is at m/e = 70.
(5) The infrared spectrum of A is shown below:

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

Transmittance (%)

Wavenumber (cm1)

(a) Deduce the empirical formula of A.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0; molar volume of any gas
at room temperature and pressure = 24.0 dm3 mol1) (3 marks)

(b) With reference to the results of (2) and (3), suggest ONE functional group
present in A. (1 mark)

(c) Write the possible structural formula of A. (4 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

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(a) Number of moles of CO2 released = = 0.0274 mol

Mass of C in 0.480 g of A = 0.0274 mol × 12.0 g mol1 = 0.329 g

Number of moles of H2O released = = 0.0205 mol

Mass of H in 0.480 g of A = 0.0205 mol × 2 × 1.0 g mol1 = 0.0410 g

Mass of O in 0.480 g of A = (0.480  0.329  0.0410) g = 0.110 g

Number of moles of O in 0.480 g of A = = 0.00688 mol

C H O
Number of moles of
0.0274 0.0410 0.00688
atoms (mol)
Mole ratio of atoms
=4 =6 =1

2
∴ empirical formula of A is C4H6O. 1
(b) A should contain a ketone group. 1
(c) Since the relative molecular mass of A is 70, the molecular formula of A
is C4H6O. 1
1
From the IR spectrum, the absorption peak at around 1620 cm
corresponds to the presence of a C=C bond. 1
1
The absorption peak at around 1700 cm corresponds to the presence of a
C=O bond. 1

Possible structure of A is . 1
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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

|!|CMELF0156400019|!|
White lactone is a compound found in white wine. Its structure is shown below.

(a) State TWO functional groups present in white lactone. (2 marks)

(b) Thin-layer chromatography (TLC) can be used to show that white lactone is
present in a sample of white wine. However, white lactone is colourless. Outline
the experimental procedure to show that white lactone is present in white wine
by thin-layer chromatography. (4 marks)

(c) Mass spectrometry can be used to determine the structure of white lactone.
(i) What is the expected molecular ion peak in the mass spectrum? (1 mark)

(ii) Suggest one chemical species corresponding to the peak at m/e = 15. (1
mark)

##
(a) Carbon-carbon double bond 1
Ester group 1
(b) Draw a baseline with a pencil across the bottom of a TLC plate. Place
drops of pure white lactone and the sample of white wine on the baseline.
Allow those spots to dry. 1
Suspend the plate in a developing solvent, with the spots above the

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

solvent level. Wrap the beaker with a piece of polyethene film. 1

When the solvent is near the top of the plate, remove the plate and dry it. 1
Place the TLC plate in an atmosphere of iodine vapour / shine ultraviolet
light on the plate. Compare the Rf value of white lactone with those of the
white wine sample. 1
(c) (i) 166 1
(ii) CH3+ 1
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|!|CMELH0156400020|!|
0.412 g of ethane was mixed with excess bromine (dissolved in an organic solvent)
under light. After an hour, the masses of mono-substituted, di-substituted and tri-
substituted ethane formed were 0.297 g, 0.094 g and 0.012 g respectively.

(a) Calculate the mole ratio of mono-substituted, di-substituted and tri-substituted

ethane after an hour of reaction.
(Relative atomic masses: H = 1.0, C = 12.0, Br = 79.9) (2 marks)

(b) Suggest how to increase the yield of tri-substituted ethane. (1 mark)

(c) A student isolated all the di-substituted ethane at a certain time interval. He
concluded that the isolated sample is pure as only one molecular peak was
observed in the mass spectrum. Do you agree? Explain your answer. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XV Analytical chemistry

##
(a) Number of mole of mono-substituted ethane

= = 2.73 × 103 mol

Number of mole of di-substituted ethane

= = 5.01 × 104 mol

Number of mole of tri-substituted ethane

= = 4.50 × 105 mol 1

∴ Mole ratio of mono-substituted ethane : di-substituted ethane : tri-

substituted ethane = 2.73 × 103 : 5.01 × 104 : 4.50 × 105 = 60.7 : 11.1 :
1 1
(b) Increase the reaction time 1
(c) Disagree. Two di-substituted ethane (1,1-dibromoethane and 1,2-
dibromoethane) were produced. 1
As the two di-substituted ethane have the same relative molecular mass,
they give the same molecular ion peak in the mass spectrum. 1
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