Cambridge International Examinations

Cambridge International Advanced Subsidiary and Advanced Level

*0134962560*

CHEMISTRY 9701/41
Paper 4 A Level Structured Questions October/November 2018
 2 hours
Candidates answer on the Question Paper.
Additional Materials: Data Booklet

READ THESE INSTRUCTIONS FIRST

Write your Centre number, candidate number and name on all the work you hand in.
Write in dark blue or black pen.
You may use an HB pencil for any diagrams or graphs.
Do not use staples, paper clips, glue or correction fluid.
DO NOT WRITE IN ANY BARCODES.

Answer all questions.

Electronic calculators may be used.

You may lose marks if you do not show your working or if you do not use appropriate units.
A Data Booklet is provided.

At the end of the examination, fasten all your work securely together.
The number of marks is given in brackets [ ] at the end of each question or part question.

This document consists of 20 printed pages.

IB18 11_9701_41/FP
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Answer all the questions in the spaces provided.

1 (a) An aldehyde, an alkane and a carboxylic acid, all of similar volatility, are mixed together. The
mixture is then analysed in a gas chromatograph.

The gas chromatogram produced is shown.

Y
absorption X

0 5 10 15 20
time / mins

The separation of the compounds depends on their relative solubilities in the stationary phase.
The stationary phase is a liquid alcohol.

(i) Complete the table to suggest which compound in the mixture is responsible for each
peak X, Y and Z. Explain your answer by reference to the intermolecular forces of the
compounds.

organic
peak explanation
compound

[2]

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(ii) A student calculates the areas underneath the three peaks in the chromatogram.

peak X Y Z
area / mm2 19 32 47

The area underneath each peak is proportional to the mass of the respective compound.

Calculate the percentage by mass in the original mixture of the compound responsible for
peak Z.

 % of mixture responsible for peak Z = .............................. [1]

(b) (i) The mass spectrum of a halogenoalkane containing one chlorine atom or bromine atom
will show an additional peak at M+2.

State the isotopes of chlorine and bromine responsible for M+2 peaks.

chlorine .................................................... bromine ............................................................

[1]

(ii) The mass spectrum of bromochloromethane, CH2BrCl, has a molecular ion peak, M, at an
m / e value of 128. It also has M+2 and M+4 peaks.

Suggest the identity of the molecular ions that give rise to these peaks.

M peak ..................................................

M+2 peak ..............................................

M+4 peak ..............................................

[2]

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(c) Halogenoalkanes can be formed from the reaction of an alkene with a hydrogen halide.

Methylpropene reacts with hydrogen bromide to form 2-bromo-2-methylpropane.

CH3 CH3

H 2C C + HBr H 3C C CH3

CH3 Br

methylpropene 2-bromo-2-methylpropane

(i) Draw the mechanism of this reaction. Include all relevant curly arrows, dipoles and charges.

[3]

(ii) 1-bromo-2-methylpropane is also formed in this reaction.

Explain why 2-bromo-2-methylpropane will be the major product in this reaction.

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

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

........................................................................................................................................ [1]

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(d) (i) Explain what is meant by the term partition coefficient, Kpartition.

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

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

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

........................................................................................................................................ [2]

(ii) T
 he partition coefficient of organic compound H between dichloromethane and water is
4.75.

●  .50 g of compound H was dissolved in water and made up to 100 cm3 in a volumetric

2
flask.
● 50 cm3 of this aqueous solution were shaken with 10 cm3 of dichloromethane.

Calculate the mass of compound H that was extracted into the dichloromethane.

 mass of compound H extracted = .............................. g [2]

 [Total: 14]

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2 (a) Ethanedioate ions, C2O42–, are bidentate ligands.

Explain what is meant by the term ligand.

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

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

............................................................................................................................................... [1]

(b) Cr3+(aq) and C2O42–(aq) ions form the complex ion [Cr(C2O4)2(H2O)2]–.

Draw two stereoisomers of this complex ion.

You may use to represent C2O42–.

O O

Cr Cr

[2]

(c) The solubility of calcium ethanedioate, CaC2O4, is 6.65 × 10–3 g dm–3 at 298 K.

(i) Write an expression for the solubility product, Ksp, of CaC2O4. Include its units.

Ksp =

 units = ..............................
[2]

(ii) Calculate the numerical value of Ksp CaC2O4 at 298 K. Give your answer in standard form
to two significant figures.

 Ksp CaC2O4 = .............................. [2]

 [Total: 7]

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3 (a) Complete the table to show the total number of unpaired electrons in the 3d and 4s orbitals of
each isolated gaseous atom.

number of unpaired electrons

3d 4s

Cr

Mn

Fe
[2]

Solid potassium manganate(VII), KMnO4, decomposes on heating

(b)  to form
manganese(IV) oxide, potassium manganate(VI) and a colourless gas.

Construct an equation for this reaction.

............................................................................................................................................... [2]

(c) Explain the origin of colour in transition element complexes.

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

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

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

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

............................................................................................................................................... [3]

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(d) The reaction scheme shows some reactions of [Cu(H2O)6]2+.

reaction 1 reaction 2
[Cu(H2O)6]2+ precipitate A solution of B
NaOH(aq) excess
NH3(aq)
reaction 3

reaction 4
CuCO3(s) solution of C
CH3CO2H(aq)

(i) Write the formulae of

precipitate A, ..............................................................

complex ion B, ............................................................

compound C................................................................
[3]

(ii) Identify a suitable reagent for reaction 3.

........................................................................................................................................ [1]

(iii) Write an equation for reaction 4.

........................................................................................................................................ [1]

(iv) Describe two visual observations that would be made during reaction 4.

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

........................................................................................................................................ [1]

(e) Platin, Pt(NH3)2Cl 2, is a neutral complex of platinum(II).

Explain why Pt(NH3)2Cl 2 has no charge.

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

............................................................................................................................................... [1]

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(f) (i) Pt(NH3)2Cl 2, displays cis-trans isomerism.

Draw the structure of trans-platin. State its shape and the Cl –Pt–Cl bond angle.

shape ................................................ Cl –Pt–Cl bond angle ...................

[2]

(ii) 
Cis-platin is an effective anti-cancer drug.

Describe the action of cis-platin in this role.

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

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

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

........................................................................................................................................ [2]

(g) The use of cis-platin can cause side effects so nedaplatin has been developed.

Nedaplatin can be synthesised from cis‑platin, Pt(NH3)2Cl 2, by replacing the two chloride ion
ligands with a single bidentate ligand as shown.

Suggest the structure for nedaplatin.

O
Pt(NH3)2Cl 2 +
cis-platin –
O O–

nedaplatin

[1]

 [Total: 19]

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4 (a) The enthalpy change of solution,  , of the Group 2 sulfates becomes more endothermic
down the group.

State and explain the trend in the solubility of the Group 2 sulfates down the group.

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

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

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

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

............................................................................................................................................... [3]

(b) (i) Write the expression for Kw , the ionic product of water.

Kw =

[1]

(ii) The numerical value of Kw increases with increasing temperature.

Place a tick () in the appropriate column in each row to show the effect of increasing the
temperature of water on the pH and on the ratio [H+] : [OH–].

effect of increasing
decrease stay the same increase
temperature of water

pH

ratio [H+] : [OH–]
[2]

(c) An aqueous solution of sodium hydroxide has a pH of 13.25 at 298 K.

Calculate the concentration of this sodium hydroxide solution.

 concentration = .............................. mol dm–3 [2]

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(d) Buffer solutions are used to regulate the pH of a solution to keep its pH value within a narrow
range.

Write two equations to describe how hydrogencarbonate ions, HCO3–, and carbonic acid,
H2CO3, control the pH of blood.

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

............................................................................................................................................... [2]

(e) The Ka for ethanoic acid is 1.75 × 10–5 mol dm–3 at 298 K.

(i) When ethanoic acid is dissolved in water, an equilibrium mixture containing two acid‑base
pairs is formed.

Write an equation for this equilibrium. In the boxes label each species acidic or basic to
show its behaviour in this equilibrium.

CH3CO2H + +
.............................. .............................. ..............................

[2]

(ii) A
 buffer solution was prepared by adding 30.0 cm3 of 0.25 mol dm–3 ethanoic acid, an
excess, to 20.0 cm3 of 0.15 mol dm–3 sodium hydroxide.

Calculate the pH of the buffer solution formed at 298 K. Give your answer to one decimal
place.

 pH = .............................. [4]

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(f) Titration curves for two different acid-base reactions, M and N, are shown.

reaction M reaction N
14 14

12 12

10 10

8 8
pH pH
6 6

4 4

2 2

0 0
0 10 20 30 40 50 0 10 20 30 40 50
volume of acid added / cm 3
volume of acid added / cm 3

(i) Use the titration curve for reaction M to deduce the volume of acid added at the end‑point
for this titration.

 volume of acid added at the end-point = .............................. cm3 [1]

(ii) The table shows some acid-base indicators.

pH range of
name of indicator
colour change
malachite green 0.2–1.8
bromocresol green 3.8–5.4
bromothymol blue 6.0–7.6
thymolphthalein 9.3–10.6

Name a suitable indicator for each of the acid-base titrations M and N. Explain your
answers.

reaction M .................................................... reaction N ....................................................

explanation ..........................................................................................................................

..............................................................................................................................................
[2]

 [Total: 19]

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5 (a) P
 olyhydroxyamide is a fire-resistant polyamide which is formed from the two monomers, F and
G.

HO2C CO2H H 2N NH2

OH
F G

(i) Predict the number of peaks that will be seen in the carbon-13 NMR spectra of F and G.

number of peaks

G
[2]

(ii) Draw the repeat unit of polyhydroxyamide. The amide bond should be shown displayed.

[2]

(b) When poly(ethene) is formed from ethene, many bonds are broken and formed.

Place one tick () in each row of the table to indicate the types of bonds broken and formed
in this process.

σ-bonds only π-bonds only both σ- and π-bonds

bonds broken

bonds formed
[2]

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(c) Addition polymers can be classified into two types.

●●  omopolymer - a polymer made up of the same monomer unit

h
●● copolymer - a polymer made up of two or more different monomer units

The reaction of propene, CH3CH=CH2, with phenylethene, C6H5CH=CH2, gives a copolymer.

Draw a length of the chain of this copolymer that contains one molecule of each monomer.

[2]

(d) (i) Polyalkenes biodegrade very slowly.

Explain why by referring to the structures of the polymers.

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

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

........................................................................................................................................ [1]

(ii) Some polymers will degrade in the environment.

Describe two processes by which this occurs.

1 ...........................................................................................................................................

2 ...........................................................................................................................................
[2]

 [Total: 11]

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6 (a) U
 se the Data Booklet to draw the structure of the dipeptide val-lys. The peptide bond should
be shown displayed.

[2]

(b) The isoelectric point is the pH at which an amino acid exists as a zwitterion. The isoelectric
point of valine is 6.0 and of lysine is 9.8.

A mixture of the dipeptide, val-lys, and its two constituent amino acids, valine and lysine, was
analysed by electrophoresis using a buffer at pH 6.0.

Draw and label three spots on the diagram of the electrophoresis paper to indicate the likely
position of each of these three species after electrophoresis. Explain your answer.

+ –

mixture applied here

explanation ..........................................................................................................................

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

..............................................................................................................................................
[5]

 [Total: 7]

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7 (a) Chlorobenzene and phenol both show a lack of reactivity towards reactants that cause the
breaking of the C–X bond (X = Cl or OH).

Explain why.

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

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

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

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

............................................................................................................................................... [3]

(b) When phenol is reacted with bromine dissolved in an inert solvent, two isomeric bromophenols,
C6H4BrOH, are formed.

Suggest structures for these products. Name each compound.

name: ..................................................................

name: ..................................................................
[2]

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(c) A student suggested that phenol can be prepared from benzene by the method shown.

NO2 NH2
step 1 step 2

step 3
NaNO2(aq) / HCl (aq)
5 °C

OH
step 4

phenol
K

(i) Suggest reagents and conditions for each of the following steps.

step 1 ...................................................................................................................................

step 2 ...................................................................................................................................

step 4 ...................................................................................................................................
[3]

(ii) Deduce the structure for K and draw its structural formula in the box. [1]

(iii) Name the mechanism for step 1.

........................................................................................................................................ [1]

(iv) Write an equation for step 2. Use [H] for the reducing agent in this equation.

[1]

 [Total: 11]

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8 Entropy is a measure of the disorder of a system.

(a) Assume the entropy, S, for H2O is zero at 0 K.

Sketch a graph on the axes to show how the entropy changes for H2O between 0 K and 300 K.

S / J K–1 mol–1

0
0 100 200 300
temperature / K
[2]

(b) Place one tick () in each row of the table to show the sign of the entropy changes, ΔS.

ΔS is negative ΔS is positive

solid dissolving in water

water boiling to steam

[1]

(c) The equation for a reaction that produces methanol is shown.

CO2(g) + 3H2(g) CH3OH(g) + H2O(g)

Use relevant bond energies from the Data Booklet to calculate the enthalpy change, ΔH, for
this gas phase reaction.

 ΔH = .............................. kJ mol–1 [2]

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(d) At 298 K, both products of this reaction are liquid.

CO2(g) + 3H2(g) CH3OH(l) + H2O(l) ΔH o = –131 kJ mol–1

Standard entropies are shown in the table.

substance CO2(g) H2(g) CH3OH(l) H2O(l)

S o / J K–1 mol–1 +214 +131 +127 +70

(i) Calculate the standard entropy change, ΔS o, for this reaction.

 ΔS o = .............................. J K–1 mol–1 [2]

(ii) Calculate the standard Gibbs free energy change, ΔG o, for this reaction at 298 K.

 ΔG o = .............................. kJ mol–1 [2]

(iii) Predict the effect of increasing the temperature on the feasibility of this reaction.

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

........................................................................................................................................ [1]

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(e) In a methanol-oxygen fuel cell, CH3OH(l) and O2(g) are in contact with two inert electrodes
immersed in an acidic solution.

The half-equation for the reaction at the methanol electrode is shown.

CH3OH + H2O CO2 + 6H+ + 6e– E o = – 0.02 V

(i) Use the Data Booklet to write an equation for the overall cell reaction.

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

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

........................................................................................................................................ [1]

(ii) Use E o values to calculate the for this reaction.

 = .............................. V [1]

 [Total: 12]

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