2010-AL

CHEM
PAPER 2
HONG KONG EXAMINATIONS AND ASSESSMENT AUTHORITY
HONG KONG ADVANCED LEVEL EXAMINATION 2010

CHEMISTRY A-LEVEL PAPER 2

1.30 am – 4.30 am (3 hours)

This paper must be answered in English

1. There are TWO sections in this paper, Section A and Section B.

2. Section A carries 60 marks and Section B carries 40 marks.

3. Answer ALL questions from both Sections A and B.

4. Answers to questions in Section A and B are to be written in the AL(C) and

AL(E) Answer Books respectively.

5. Some constants, characteristic infra-red absorption wavenumber ranges, standard

reduction potentials and a Periodic Table can be found on pages 12, 13 and 14 of
this question book.

© 香港考試及評核局 保留版權 Not to be taken away before the

Hong Kong Examinations and Assessment Authority end of the examination session
All Rights Reserved 2010

2010-AL-CHEM 2–1
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 SECTION A

Answer ALL questions, using the AL(C) Answer Book.

1. (a) The following shows the data from a study of mass spectrometry on a compound X. Three
bbbbbbbbbbbbbbchemical species and the respective mass to charge ratios are hidden from the data.

m/z chemical species

162 (127I35Cl)+

164 (127I37Cl)+

197 (127I35Cl2)+

199 (127I35Cl37Cl)+

201 (127I37Cl2)+

232 (127I35Cl3)+

234 (127I35Cl237Cl)+

236 (127I35Cl37Cl2)+

238 (127I37Cl3)+

(I) Deduce the hidden chemical species and the respective mass to charge ratios.

(II) Sketch the original mass spectrum on your Answer Book.

(iii) (I) Deduce the molecular geometry of X.

(II) Calculate the relative molecular mass of X.

(III) The relative molecular mass of X in benzene doubles its expected value.
Explain.

(7 marks)

2010-AL-CHEM 2–2
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1. (b) Calcium carbide (CaC2) crystallizes in a lattice structure of the following unit cell.

(i) Determine the number of calcium ions and a carbide ((C≡C)2-) ions in an unit cell and
hence calculate the volume of an unit cell.

(Given: the density of CaC2 = 2.22 g cm-3)

(ii) Calcium carbide reacts with nitrogen to form calcium cyanamide(CaCN2) at high
temperature.

(I) Draw the electronic structure of calcium cyanamide.

(II) Write a chemical equation for the formation of calcium cyanamide.

(III) Calculate the percentage composition of nitrogen in calcium cyanamide and

hence suggest ONE of its applications.

(iii) Assume calcium cyanamide crystallizes in a lattice structure identical to calcium carbide,
compare their expected melting points in terms of electrostatic interaction. Explain.

(8 marks)

(c) Hydrogen peroxide (H2O2) is a pale blue liquid which appears colourless in diluted form.

(i) Hydrogen peroxide is a stronger bleaching agent with a manganese based catalyst than
without, which is more obvious at high temperature.

Explain.

(ii) Hydrogen peroxide exhibits many properties in common with chlorine.

(I) Which of their use as a bleaching agent, hydrogen peroxide with a manganese
based catalyst or sodium chlorite, is more environmentally benign ?

Explain.

(II) In a process of paper manufacturing, chlorine is replaced by hydrogen peroxide

mixed with an iron based catalyst to remove lignin from wood pulp.

Give an advantage of such a practice.

(5 marks)

2010-AL-CHEM 2–3
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2. (a) Bromide ion reacts with bromate(V) ion according to the equation shown below:

5Br-(aq) + BrO3-(aq) + 6H+(aq) Æ 3Br2(aq) + 3H2O(aq)

(i) (I) Write the chemical equation for the reaction between bromine and phenol.

(II) Methyl orange can be bleached by bromine. Explain how the above progress of
reaction can be monitored by addition of phenol and methyl orange.

Hint: Hydroxyl group is an electron-donating substituent.

(ii) The experiment in an attempt to find the initial rate was carried out under different
temperature. The following lists the results:

Experiment Temperature / oC Time for specific event to happen / s

1 30 1054
2 37 595
3 41 387
4 44 306
5 49 211

(I) Suppose the specific event indicates the absence of bromine in the reaction
mixture. Derive an expression correlating the time for the specific event to
happen t and the activation energy Ea.

(II) Hence, or otherwise, determine the Ea by plotting a suitable graph.

(Given: Arrhenius equation: k = Ae-Ea/RT)

(8 marks)

(b) (i) State ONE characteristic of a dynamic equilibrium and ONE application, other than
ffffkkkkkkkkfffffsolvent extraction, of partition coefficient.

(ii) In an experiment to determine the structure of a copper complex, 5 M NH3(aq) was added
into 1 M CuSO4(aq) and was shaken to form the complex N. Afterwards, CCl4(l) was
added into the mixture in a separating funnel and the resulting mixture was shaken again.
25 cm3 of the organic layer was extracted and titrated against with HCl(aq). 9.63 cm3 of
0.1 M HCl(aq) was required to attain complete neutralisation.

(At 298 K, the partition coefficient of NH3 between CCl4(l) and H2O(l) is 0.04.)

(I) Determine the coordination number of copper in N.

(II) Deduce the structure of N.

(5 marks)

2010-AL-CHEM 2–4
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2. (c) The major buffer system in maintaining a certain pH value of venous blood is shown below:

CO2 + H2O H+ + HCO3- Ka = 8.30 x 10-7 mol dm-3

(i) Explain how the system works as a buffer when OH- ions are introduced into the system.

(ii) Given that the ratio of [HCO3-] to [CO2] = 20 : 1 , calculate the approximate pH value of
normal blood sample.

(iii) The quantity of CO2 + HCO3- content can be determined by the following procedures.

1. Heat 200 cm3 of blood sample with excess dilute sulphuric(VI) acid.

2. Absorb the carbon dioxide evolved using barium hydroxide.

3. Filter off the barium carbonate precipitate.

4. Dry the precipitate and weigh it.

Given that 0.8 g of barium carbonate was formed in a determination, write the chemical
equation for the reaction that occurred and calculate the total number of mole of CO2 +
HCO3- in the blood sample used.

(iv) Using the above information, determine the approximate concentration CO2(aq) in a
normal blood sample.

(7 marks)

2010-AL-CHEM 2–5
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3. (a) Lead-acid accumulator is a secondary cell commonly used as car batteries.

V
H2SO4(aq)

Pb(s) and Pb(s) and spongy

spongy Pb(s)
PbO2(s)

(i) Is a porous partition necessary for the above cell ? Explain.

(ii) The following table shows the reaction occuring at the electrodes of the cell.

Reaction Potential / V

Anode Pb(s) + SO42-(aq) PbSO4(s) + 2e- + 1.69

Cathode PbO2(s) + 4H+(aq) + SO42-(aq) + 2e- 2PbSO4(s) + 2H2O(l) + 0.36

(I) Calculate the voltage the cell can generate.

(II) State the positive electrode for the lead acid accumulator.

(III) Write the full chemical equation for the reaction that occurs.

Indicate the direction of equilibrium as ‘charging’ and ‘discharging’ properly.

(IV) Explain why it is not desirable to charge the accumulator too rapidly.

(V) Suggest a physical method to monitor the status of charge for the above cell.

Explain the principle behind.

(8 marks)

2010-AL-CHEM 2–6
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3. (b) Account for each of the following.

(i) The vaporization enthalpy of ethanol is greater than that of ethanal.

(ii) Sodium nitrate decomposes at a lower temperature than potassium nitrate.

(iii) Although dissolution of PbCl2(s) in water is an exothermic process, it is spontaneous

under standard conditions.

(iv) Upon treatment with concentrated sulphuric(VI) acid, sodium chloride and sodium
bromide yields different analogues.

(8 marks)

(c) Tymol blue is a indicator employed in acid-base titrimetric analysis.

HO OH HO O O- O

pK1 = 1.7 pK2 = 8.9

O
S O SO3- SO3-
O

red
yellow blue

Tymol blue transitions at pH 1.2–2.8 and at pH 8.0–9.6 respectively. Deduce the corresponding
dominating species and colour of tymol blue in a buffer solution of

(i) pH 7 and

(ii) pH 14.

Explain your answer.

(4 marks)

.
END OF SECTION A

2010-AL-CHEM 2–7
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 SECTION B

Answer ALL questions, using the AL(E) Answer Book.

4. (a) The following shows the structure of three amines A, B and C.

NH2 NH2 H
N

A B C

(i) Arrange amines A, B and C in increasing order of basicity. Explain your ordering.

(ii) State the number of carbon atom(s) which exhibit one-third of s-orbital character in
amine B. Explain your answer.

(iii) Discuss the aromaticity of amines A, B and C.

(5 marks)

4. (b) Loratadine, a prescription drug indicated for the symptomatic relief of allergy has the following
structure:

Cl

O O

(i) Loratadine is commonly known as a tricyclic anti-histamine.

(I) State the number of aromatic ring(s) in the above structure. Explain.

(II) Propose a mechanism for its pharmacological effects.

(ii) An equimolar of loratadine and 2-chloro-2-methylpropane are treated with ethanolic

silver nitrate solution respectively.

(I) Draw the structure of 2-chloro-2-methylpropane.

(II) Give the expected observation in each of the above cases.

(III) Explain, in terms of the bonding and structure, why they differ in behaviour
towards the hydrolysis.

(7 marks)

2010-AL-CHEM 2–8
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4. (c) Epoxy resin can be obtained phenol and propene via the following route.

Step 1 OH Step 2 Step 3

O O
CH2 Cl Cl
polymerization

OH Epoxy resin
CH3
(CH3)2CO HO OH
CH3
bisphenol A

(i) Suggest reactant(s) and conditions for each of Steps 1, 2 and 3.

(ii) Outline the mechanism for the reaction in Step 1.

(iii) Name the type of reaction for the formation of bisphenol A from phenol.

(iv) Draw a portion of epoxy resin and hence discuss the following properties with regards to
its structure and bonding.

(I) biodegradability

(II) thermostability

(9 marks)

2010-AL-CHEM 2–9
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5. (a) Serotonin (5-hydroxytryptamine) is a monoamine neurotransmitter, which is commonly present in
fungi. Its structure is shown below:

HO
.

HN NH2

(i) Draw the structure of major organic products formed when it is treated with

(I) sodium hydroxide solution.

(II) sodium hydrogencarbonate solution.

(ii) It is known that the Ka of its ammonium salt is 2.0  x  10-7 and the that of phenolic
hydroxyl group is 1.58 x 10 -10. Suggest how you would extract serotonin from a sample
of mushroom.

(5 marks)

(b) Outline a synthetic route with no more than five steps to accomplish the following transformations.
For each step, give the reagent(s), conditions and the structure of organic product.

(i)
CH2OH CH2CONH2

(ii)
CN

CN

(7 marks)

2010-AL-CHEM 2–10
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5. (c) Figure 5.1 and Figure 5.2 below show the infra-red spectrum and mass spectrum of compound K,
with a relative molecular mass of 58 and composition by mass: C : 62.1%; H : 10.3%; O : 27.6%.

Based on the information in the figure and the data provided, deduce the structure of K.

transmittance (%)

wavenumber / cm-1

Figure 5.1 Infra-red spectrum of K

relative intensity (%)

m/z

Figure 5.2 Mass spectrum of K

(7 marks)
END OF PAPER

2010-AL-CHEM 2–11
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 Constants

Gas constant, R = 8.31 J K-1 mol-1

Avogadro constant, L = 6.02 x 1023 mol-1

Plank constant, h = 6.63 x 10-34 J s

Speed of light in vacuum, c = 3.00 x 108 m s-1

Ionic product of water at 298 K, Kw = 1.00 x 10-14 mol-2 dm-6

Specific heat capacity of water = 4.18 J g-1 K-1

Characteristic Infra-red Absorption Wavenumber Ranges

(Stretching modes)

Bond Compound type Wavenumber range /cm-1

C=C Alkene 1610 to 1680
C=O Aldehydes, ketones, carboxylic acids and derivatives 1680 to 1800
C≡C Alkynes 2070 to 2250
C≡N Nitriles 2200 to 2280
O–H Acids (hydrogen-bonded) 2500 to 3300
C–H Alkanes, alkenes, arenes 2840 to 3095
O–H Alcohols, phenols (hydrogen-bonded) 3230 to 3670
N–H Amines 3350 to 3500

2010-AL-CHEM 2–12
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2010-AL-CHEM 2–13
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2010-AL-CHEM 2–14
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