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Musab Ocr

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Musab Ocr

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1 * The organic compound A is unsaturated and is a trans stereoisomer.

Compound A has the following composition by mass: C, 55.8%; H, 7.0%; O, 37.2%.

The mass spectrum and the infrared spectrum of compound A are shown below.

Use the information to determine the structure of compound A.

Explain your reasoning and show your working.

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2
A student was asked to carry out an experiment to determine the initial rate of reaction of zinc and
hydrochloric acid.

The student plans to collect a total of about 72 cm3 of hydrogen at RTP and to use an excess of zinc.

The student selects the following apparatus:

the apparatus shown in the diagram
100 cm3measuring cylinder
stop clock
2 decimal place balance

Outline how the student could carry out the experiment and explain how the results could be processed
graphically.
Show all working in your calculations.

Describe the oxidation reactions of butan-1-ol forming an aldehyde and a carboxylic acid.

Explain, using a diagram, how the aldehyde can be produced in the laboratory by controlling the reaction
conditions.

[6]

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4
1-Bromobutane is an organic liquid with a boiling point of 102 °C.

A student prepares 1-bromobutane by reacting butan-1-ol with sulfuric acid and sodium bromide. The student
boils the mixture for one hour.

The equation is shown below.

CH3CH2CH2CH2OH + H+ + Br− → CH3CH2CH2CH2Br + H2O

The student obtains a reaction mixture containing an organic layer (density = 1.27 g cm−3) and an aqueous layer
(density = 1.00 g cm−3).

(i) * Draw a labelled diagram to show how you would safely set up apparatus for the preparation. Outline a
method to obtain a pure sample of 1-bromobutane from the reaction mixture.

(ii) The student used 0.150 mol of butan-1-ol. The student obtained a 61.4% percentage yield of
1-bromobutane.

Calculate the mass of 1-bromobutane obtained.

Give your answer to three significant figures.

mass = g [2]

5 * Compound F is a trans stereoisomer which is a useful intermediate in organic synthesis.

The results of elemental and spectral analysis of compound F are shown below.

Percentage composition by mass: C, 68.6 %; H, 8.6 %; O, 22.8 %.

Infrared spectrum

In the mass spectrum, the peak with the greatest relative intensity is caused by the loss of a functional group
from the molecular ion of compound F.

Determine the structure of compound F.

Explain your reasoning and show your working.

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6 * The structures of alcohols A–F are shown below.

Compound X is one of the alcohols A–F.

A student refluxes compound X with acidified potassium dichromate(VI) as an oxidising agent. A pure sample of
the organic product Y is obtained from the resulting mixture. The mass spectrum and IR spectrum of Y are
shown below.

Mass spectrum of Y

IR spectrum of Y

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Using this information, identify compound X and product Y, and write an equation for the formation of product Y
from compound X. You may use [O] to represent the oxidising agent.

In your answer you should make clear how your conclusions are linked to the evidence.

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7 A student carries out an investigation to find the enthalpy change for the decomposition of magnesium
carbonate, ΔH1 (Reaction 1).

Reaction 1 MgCO3(s) → MgO(s) + CO2(g) ΔH1

This enthalpy change cannot be found directly. It can be determined indirectly from the enthalpy changes for the
reactions below, which can be found by experiment.

Reaction 2 MgCO3(s) + 2HCl (aq) → MgCl 2(aq) + H2O(l) + CO2(g) ΔH2

Reaction 3 MgO(s) + 2HCl (aq) → MgCl 2(aq) + H2O(l) ΔH3

The enthalpy cycle is shown in Fig. 4.1.

Fig. 4.1

Determination of ΔH2 for Reaction 2

Student’s method
• Weigh a 250 cm3 polystyrene cup.
• Add about 100 cm3 of 2.00 mol dm–3 hydrochloric acid (an excess) to the polystyrene cup and record the
initial temperature of the HCl (aq).
• Add 4.215 g MgCO3, stir the mixture, and record the final temperature.
• Weigh the polystyrene cup containing the final solution.

Results

Mass of polystyrene cup / g 21.415

Mass of polystyrene cup + final solution / g 124.425
Initial temperature of HCl (aq) / °C 20.40
Final temperature of solution / °C 25.40

Determination of ΔH3 for Reaction 3

The student uses the same method as for Reaction 2 but with MgO in place of MgCO3.

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The student calculates ΔH3 for Reaction 3 as –136.1 kJ mol–1.

Use the student’s results to calculate ΔH2 for Reaction 2 and determine the enthalpy change ΔH1 , in kJ mol–1,
for the decomposition of magnesium carbonate (Reaction 1), using the energy cycle in Fig. 4.1.

Assume the specific heat capacity, c, of the reaction mixture is the same as for water.

8 This question is about nickel and its compounds.

A student is provided with samples of three nickel compounds.

One sample is nickel(II) bromide, another is nickel(II) sulfate and the third is nickel(II) carbonate. The student
doesn’t know which sample is which.

Describe the tests that the student could carry out to identify the anion (negative ion) in each sample, and write
equations for any reactions.

9(a) This question is about hex-1-ene, CH3CH2CH2CH2CH=CH2.

Hex-1-ene is a liquid with a boiling point of 63 °C and a density of 0.67 g cm–3.

Hex-1-ene can be prepared by refluxing hexan-1-ol (boiling point 157 °C) with an acid catalyst.

Hexan-1-ol is a liquid with a boiling point of 157 °C and a density of 0.82 g cm–3.

The equation is shown below.

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After reflux, the resulting mixture contains unreacted hexan-1-ol, hex-1-ene and water.
The mixture is then purified.

The expected percentage yield of hex-1-ene from hexan-1-ol is 62.5%.

(i) * A student plans to prepare 4.20 g of hex-1-ene by this method.

Calculate the mass of hexan-1-ol that the student should use and explain how you could obtain pure
hex-1-ene from the mixture obtained after reflux.

(ii) Another student suggested that hex-1-ene could be prepared from hexan-2-ol by the same method.

Would you expect the percentage yield of hex-1-ene to be greater than, less than or about the same as when
using hexan-1-ol?

Explain your answer.

[2]

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(b) Hex-1-ene can also be polymerised to form poly(hex-1-ene).

(i) Draw a section of poly(hex-1-ene) containing two repeat units.

[1]

(ii) Waste poly(hex-1-ene) can be disposed of usefully by recycling.

State two other methods of disposing of polymers that can be beneficial to the environment.

[2]

10 Magnesium nitrate is used in fertilisers as a source of nitrogen.

* A student plans to prepare 250.0 cm3 of a 0.4000 mol dm–3 solution of magnesium nitrate, starting from
magnesium nitrate crystals, Mg(NO3)2•6H2O.

Describe how the student would prepare the solution, giving full details of quantities, apparatus and method.

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11 2-Chloro-2-methylpropane, (CH3)3CCl , is an organic liquid with a boiling point of 50 °C.

A student prepares (CH3)3CCl by reacting 2-methylpropan-2-ol, (CH3)3COH, with concentrated hydrochloric acid.

The student’s method for the preparation is outlined below.

• Add 10.0 cm3 (7.70 g) of (CH3)3COH and 30 cm3 concentrated hydrochloric acid (an excess) to a round-
bottom flask. Stopper the flask.
• Shake the flask until the mixture separates into two layers.

Densities: (CH3)3CCl : 0.85 g cm–3; concentrated HCl : 1.18 g cm–3

After purification, the percentage yield of (CH3)3CCl is 76%.

Explain how the student could obtain a pure, dry sample of (CH3)3CCl from the mixture in the flask and calculate
the mass of pure (CH3)3CCl that would be expected from this preparation.

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12 This question is about the manufacture of hydrogen, H2.

In industry, hydrogen is manufactured from methane, as shown in Equilibrium 4.1.

CH4(g) + H2O(g) ⇌ CO(g) + 3H2(g) ΔH = +206 kJ mol–1 Equilibrium 4.1

The industrial process is carried out at 15 atmospheres pressure and at a temperature of 800°C using an excess
of steam. A nickel catalyst is used.

(i) * Explain why these conditions are used industrially.

(ii) A chemist mixes CH4(g) and H2O(g) and leaves the mixture to reach equilibrium.

CH4(g) + H2O(g) ⇌ CO(g) + 3H2(g) ΔH = +206 kJ mol–1 Equilibrium 4.1

The equilibrium mixture contains the following concentrations.

Substance Concentration/mol dm–3

CH4(g) 0.111
H2O(g) 0.682
CO(g) 0.510
H2(g) 1.530

Write an expression for the equilibrium constant, K c, for Equilibrium 4.1 and calculate the numerical value of
K c.

Give your answer to 3 significant figures.

K c = ......................................... mol2 dm–6 [2]

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13 This question is about halogens and halogen compounds.

Seawater contains very small quantities of dissolved iodide ions.

The concentration of potassium iodide, KI, in seawater is 0.150 g dm–3.

Iodine can be extracted by bubbling chlorine gas through seawater.

Explain why chlorine is more reactive than iodine and determine the volume, in dm3, of seawater that is needed
to manufacture 1.00 tonne of iodine, I2.

[6]

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14 This question is about the enthalpy change of combustion of alcohols.

A student carries out an experiment to determine the enthalpy change of combustion, ΔcH, of butan-1-ol,
CH3CH2CH2CH2OH.

The student sets up the apparatus as shown below.

The student’s results are shown in the table below.

Initial temperature of water / °C 18.5

Final temperature of water / °C 49.5
Mass of burner before heating / g 212.38
Mass of burner after heating / g 211.07

(i) The thermometer had an uncertainty of ± 0.25 °C in each temperature reading.

Calculate the percentage uncertainty in the temperature change.

percentage uncertainty = ...................................................... % [1]

(ii) Use the student’s results to determine ΔcH of butan-1-ol in kJ mol–1.

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Explain why this value of ΔcH is different from the data book value and suggest how the experimental design
could be modified to improve the accuracy of the ΔcH value obtained.

[6]

(iii) Another student carries out the experiment in 4(b) using 150 g of water in the beaker instead of 200g.

Calculate the mass of butan-1-ol that would produce the same temperature rise as in the experiment in 4(b).

Assume the same heat losses.

mass of butan-1-ol = ....................................................... g [1]

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15 An alcohol A contains carbon, hydrogen and oxygen only. The alcohol is a liquid at room temperature and
pressure but can easily be vaporised.

1.15 g of A produces 761 cm3 of gas when vaporised, measured at 100 kPa and 366 K.

Determine the molar mass of compound A and draw a possible structure for A.

Show all your working.

molar mass = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g mol–1

[5]

Propene, drawn below, contains both σ- and π-bonds. The C−H and C−C single bonds are σ-bonds. The C=C
double bond is made up of a σ-bond and a π-bond.

(i) Describe how a σ-bond forms.

[1]

(ii) State the bond angle and shape around each carbon atom of the C=C double bond in propene.

bond angle:

shape:
[1]

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(b) Propene reacts with bromine, Br2. In this reaction, bromine acts as an electrophile.

(i) Outline the mechanism of this reaction.

Include curly arrows, relevant dipoles and the structures of the intermediate and final product(s).

[4]

(ii) What does a curly arrow represent in a reaction mechanism?

[1]

(c) Pent-1-ene, CH3CH2CH2CH=CH2, is an alkene with molecular formula C5H10.

(i) Pent-1-ene does not show stereoisomerism.

Explain why.

[1]

(ii) A structural isomer of pent-1-ene shows cis—trans stereoisomerism.

Draw structures for the cis and trans isomers of this structural isomer of pent-1-ene.

[2]

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(d) The following molecule shows E/Z isomerism.

Use the Cahn—Ingold—Prelog priority rules to identify whether this alkene is an E or Z stereoisomer. Explain
how you came to your decision.

[1]

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17(a) The graph below shows the variation in boiling points of the Group 16 hydrides.

(i) The variation in boiling point can be explained by intermolecular bonding.

Explain why H2S has a lower boiling point than H2O and H2Se.

[4]

(ii) Polonium, Po, is at the bottom of Group 16. Its hydride has the formula H2Po.
Estimate from the graph the boiling point of H2Po.
The relative molecular mass of H2Po is 211.

[1]

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(b) The compounds SO2 and MgO both contain oxygen.

The table below shows the melting point of both compounds:

Compound Melting point / K

SO2 200
MgO 3125

Predict the type of structure and bonding of SO2 and MgO and explain the difference in their melting points.

[4]

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18(a) This question looks at groups in the periodic table.

Calcium and strontium are Group 2 metals. They both react with water.
A chemist reacts 0.200 g of strontium with 250 cm3 water, leaving a colourless solution containing strontium
ions. The volume remains at 250 cm3.

(i) Write an equation for the reaction between strontium and water.

Include state symbols.

[1]

(ii) Calculate the concentration, in mol dm−3, of strontium ions in the resulting solution.

concentration of strontium ions = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ mol dm−3 [2]

(iii) A student plans to carry out this experiment using 0.200 g of calcium instead of 0.200 g of strontium.
Predict the difference, if any, between the volume of gas produced by calcium and strontium.
Explain your reasoning and include a calculation in your answer.

[3]

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(b) Ionisation energies can provide evidence for electron structure.
Write an equation for the first ionisation energy of chlorine.
Include state symbols.

[1]
(c) The following data shows the first eight successive ionisation energies of an element.

Ionisation 1st 2nd 3rd 4th 5th 6th 7th 8th

energy
Energy / 590 1145 4912 6474 8144 10 496 12 320 14 207
−1
kJ mol

In which group of the periodic table would this element be found?

Use the data to justify your choice.

group:

justification:

[2]

19(a) Butane, C4H10, is a highly flammable gas, used as a fuel for camping stoves. Butane reacts with oxygen as in the
equation below:

C4H10(g) + 6.5O2(g) → 4CO2(g) + 5H2O(l)

Explain why this equation represents the standard enthalpy change of combustion of butane.

[1]

(i) The use of portable heaters in enclosed spaces can result in potential dangers if incomplete combustion
takes place.
Explain the potential danger of incomplete combustion.

[1]

(ii) A portable heater is lit to heat a room.

The heater burns 600 g of butane and consumes 1.50 m3 of O2, measured at room temperature and
pressure.
Determine whether this portable heater is safe to use.
Show all your working.

conclusion, with reason:

[3]

(c) Alkane X can be used as a fuel.

Complete combustion of 0.0117 mol of X produces 2.00 × 10−3 m3 of carbon dioxide gas, measured at 24.0 °C
and 101 kPa.
Determine the molecular formula of X.
Show all your working.

molecular formula of X = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [4]

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(d) Butane can be produced from decane, C10H22, as shown in the equation below.

C10H22(l) → C4H10(g) + 2C3H6(g)

Standard enthalpy changes of combustion, ΔcH⦵, are shown in the table below.

Substance Δc H⦵ / kJ mol−1
C10H22(l) −6778
C4H10(g) −2877
C3H6(g) −2058

Calculate the standard enthalpy change of reaction, ΔrH⦵, for the reaction. Include the sign.

C10H22(l) → C4H10(g) + 2C3H6(g)

ΔrH⦵ = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ kJ mol−1 [2]

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20(a) The following reaction is used in industry to make sulfur trioxide gas, SO3.

2SO2(g) + O2(g) 2SO3(g) ΔH⦵ = −196 kJ mol−1

This preparation is carried out in the presence of a catalyst.

* Explain the conditions of temperature and pressure that could be used to obtain the maximum equilibrium yield
of sulfur trioxide.
Discuss the importance of a compromise between equilibrium yield and reaction rate when deciding the
operational conditions for this process.

[6]

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(b) An experiment is carried out to find the rate of this reaction:

2SO2(g) + O2(g) 2SO3(g)

The results of the experiment are given in the table below:

Time / s 0 50 100 150 200 250 300 350

Concentration of 0 0.024 0.034 0.038 0.039 0.040 0.041 0.041
−3
SO3 / mol dm

(i) Plot a graph from the data provided.

Include a line of best fit.

[3]

(ii) Use the graph to determine the initial rate of this reaction.

initial rate = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ mol dm−3 s−1 [2]

(iii) This experiment is repeated in the presence of a catalyst.

Draw and label a line on the graph to show the results of the catalysed experiment over the same time
period.

[1]

(c) A solid catalyst, vanadium(V) oxide, V2O5, is used in industry to increase the rate of the production of sulfur
trioxide, SO3, in this reaction.

2SO2(g) + O2(g) 2SO3(g) ΔH⦵ = −196 kJ mol−1

(i) Explain, with a reason, whether V2O5 is a homogeneous or heterogeneous catalyst.

[1]

(ii) The use of catalysts in industrial processes can be beneficial to the environment.
State one reason for this.

[1]

(iii) Using a fully labelled Boltzmann distribution on the grid below, explain why adding a catalyst increases
the rate of a reaction.

21(a) A student carries out a titration to determine the molar mass of an unknown acid, A.

The student dissolves 2.24 g of acid A in distilled water and makes the solution up to 250.0 cm3.
The student titrates a 25.0 cm3 portion of this solution with 0.120 mol dm−3 NaOH.
25.25 cm3 of 0.120 mol dm−3 NaOH are required to reach the end point.

The student is not confident that their titre is accurate.

Suggest what the student should do next to reduce the effect of any random error in the titration.

[2]

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(b) The acid reacts with NaOH in a 1 : 1 molar ratio.
Calculate the molar mass of acid A.

molar mass of acid A = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g mol−1 [3]

make up the acid solution to 250.0 cm3

measure the 25.0 cm3 portion of acid solution.

make up the acid solution to 250 cm3:

measure the 25.0 cm3 portion:

[1]

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22 * You are provided with three alcohols that are structural isomers: CH3CH2CH2CH2OH, CH3CH2CHOHCH3 and
(CH3)3COH. You do not know which is which.
You have access to normal laboratory apparatus and chemicals, Quickfit apparatus, and an infrared
spectrometer.
Describe a plan that would allow you to identify the three alcohols using the same experimental set up and
method.

You should provide

equations using structural formulae for any reactions

a description of how you will identify the three alcohols from any observations and results.

[6]

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23(a) Group 2 elements are metals that react with oxygen and water.

Magnesium is oxidised when it burns in oxygen to form an ionic compound.

(i) Write the electron configuration, in terms of sub-shells, of a magnesium atom.

[1]

(ii) Explain what happens when magnesium is oxidised in terms of electron transfer.

[1]

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(b) A student reacts a Group 2 metal, M, with water.

M(s) + 2H2O(l) → M(OH)2(aq) + H2(g)

The student measures the volume of hydrogen gas produced.

0.162 g of the metal produces 97.0 cm3 of gas measured at room temperature and pressure.

(i) Draw a labelled diagram of the apparatus that can be used to carry out this experiment.

[2]

(ii) Identify the Group 2 metal, M.

Show your working.

Group 2 metal = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]

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(c) The student plans to repeat the experiment using the same mass of a Group 2 metal from further down the
group.

Predict whether the volume of hydrogen produced would be greater than, less than or the same as the volume in
the first experiment.

Explain your answer.

[1]
(d) The trend in the first and second ionisation energies of Group 2 elements can be linked to the increase in
chemical reactivity down the group.

The first and second ionisation energies of calcium and strontium are given in the table.

Element First ionisation energy / kJmol–1 Second ionisation energy /

kJmol–1
Ca 590 1145
Sr 550 1064

(i) Write an equation, including state symbols, to represent the second ionisation energy of strontium.

[1]

(ii) Explain why the first ionisation energy of strontium is less than the first ionisation energy of calcium.

[3]

24(a) The graph shows the melting points of the elements in Period 3 of the periodic table.

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Phosphorus and chlorine have simple molecular structures.
More information about phosphorus and chlorine is given in the table below.

Element Molecular formula

phosphorus P4
chlorine Cι2

Explain the differences in the melting points of phosphorus and chlorine.

[3]

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(b) Magnesium and silicon have different types of giant structures.

Describe the bonding in magnesium and in silicon.

Include the names of the particles and describe the forces between the particles in the structures.

[4]
(c) Aluminium forms a sulfide, Aι2S3.

Aι2S3 reacts with water to form aluminium hydroxide and hydrogen sulfide, H2S.

Write an equation for the reaction of Aι2S3 with water.

[1]

25(a) Compound A is an alkene.

The C=C bond in a molecule of compound A has restricted rotation because it comprises a σ bond and a π
bond.

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(i) Describe one difference between the σ bond and the π bond.

[1]

(ii) Explain why compound A does not have E/Z isomers.

[1]

(iii) A structural isomer of compound A has E/Z isomers.

Draw the structure of the Z isomer and then name this isomer.

name _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

[2]

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(b) Compound A can be made from alcohol B by heating with an acid catalyst.

Suggest two possible structures for alcohol B .

[2]
(c) *Compound A reacts with hydrogen bromide to form a mixture of two different organic products.

Give the structures of the two possible organic products of the reaction.

Outline the mechanism, using the ‘curly arrow’model, for the formation of one of the organic products from
compound A.

Explain which of the two organic products is more likely to be formed.

26(a) Nitrogen forms several different oxides.

N2O is a useful anaesthetic and NO has been linked to the depletion of ozone in the stratosphere.

The standard enthalpy changes of formation of N2O and NO are given in the table.

Compound ΔfHƟ / kJ mol−1

N2O (g) + 82.0
NO (g) + 90.2

(i) Explain, in terms of bond breaking and bond making, why the enthalpy change of formation of NO is
endothermic.

[1]

(ii) Draw a fully labelled enthalpy profile diagram to represent the enthalpy change of formation of N2O.

The formulae, with state symbols, of the reactants and products should be included as part of the diagram.

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You are not expected to show the activation energy for the reaction.

[2]

(b) N2O is supplied as a compressed gas in steel cylinders for use as an anaesthetic.
The cylinders are stored at 20.0 °C.

Calculate the gas pressure, in Pa, in a 2.32 dm3 steel cylinder containing 187 g of N2O gas.

Give your answer in standard form to three significant figures.

pressure = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Pa [4]

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(c) NO radicals catalyse the breakdown of ozone in the stratosphere.

Write two equations to show how NO radicals catalyse this breakdown.

[2]

27(a) A student investigates the reaction between strontium carbonate and dilute nitric acid.

SrCO3 + 2HNO3 → Sr(NO3)2 + CO2 + H2O

The rate of reaction is determined from the loss in mass over a period of time.

(i) Explain why there is a loss in mass during the reaction.

[1]

(ii) An excess of strontium carbonate, SrCO3, is mixed with 20.0 cm3 of 1.25 mol dm−3 nitric acid, HNO3.

Calculate the mass of SrCO3 that reacts with the HNO3.

mass = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g [3]

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(b) The student plots a graph of total mass (reagents + container) against time.

(i) Describe and explain the change in the rate of the reaction during the first 200 seconds of the experiment.

[2]

(ii) Using the graph, calculate the rate of reaction, in g s−1, at 200 seconds.

Show your working on the graph.

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rate of reaction = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g s−1 [2]

Your answer should include the apparatus required and the procedure for the experiment.

[3]

28(a) This question is about the properties and reactions of butan-2-ol.

Some properties of butan-2-ol are listed in the table.

Melting point –115 °C

Boiling point 99.5 °C

Why is butan-2-ol classified as a secondary alcohol?

[1]

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(b) The shape around the oxygen atom in butan-2-ol is non-linear.

Predict the C–O–H bond angle and explain this shape.

bond angle _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

explanation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

[4]

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(c) Butan-2-ol can be oxidised by heating with an oxidising agent.

(i) Write an equation for the reaction.

Use [O] to represent the oxidising agent and show the structure of the organic product.

[2]

(ii) A student plans to carry out this oxidation using the apparatus shown in the diagram.

Give one reason why the apparatus is not suitable and describe a more suitable way of carrying out this
oxidation.

[2]

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(d) 20.2 g of butan-2-ol is reacted with excess sodium bromide and sulfuric acid.

CH3CH(OH)CH2CH3 + NaBr + H2SO4 → CH3CHBrCH2CH3 + NaHSO4 + H2O

25.2g of CH3CHBrCH2CH3 is formed.

Calculate the percentage yield of CH3CHBrCH2CH3.

percentage yield = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ % [3]

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29 * Organic compound C has the following percentage composition by mass:
C, 54.5%; H, 9.1%; O, 36.4%.

The infrared spectrum and mass spectrum of compound C are shown below.

In the mass spectrum, a secondary carbocation is responsible for the peak with the greatest relative intensity.

Identify compound C.

In your answer you should make clear how your conclusion is linked to all the evidence.

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30(a) Barium combines with oxygen, chlorine and nitrogen to form ionic compounds.

Barium oxide, BaO, has a giant ionic lattice structure.

(i) State what is meant by the term ionic bond.

[1]

(ii) Draw a ‘dot-and-cross’ diagram to show the bonding in barium oxide.

Show outer electrons only.

[2]

(iii) Calculate the number of barium ions in 1.50 g of barium oxide.

Give your answer in standard form and to three significant figures.

number of barium ions = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [2]

(b) Barium chloride, BaCl2, is soluble in water.

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(i) Compare the electrical conductivities of solid and aqueous barium chloride.

Explain your answer in terms of the particles involved.

[2]

(ii) Describe the use of aqueous barium chloride in qualitative analysis.

[2]

(iii) Hydrated barium chloride can be crystallised from solution.

Hydrated barium chloride has the formula BaCl2•xH2O and a molar mass of 244.3 g mol −1.

Determine the value of x in the formula of BaCl2•xH2O.

Show your working.

x = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [2]

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(c) Barium nitride is formed when barium is heated with nitrogen.

(i) Complete the electron configuration of a nitride ion.

1s2 [1]

(ii) Solid barium nitride is reacted with water, forming an alkaline solution A and an alkaline gas B.

Identify A and B.

Write an equation, including state symbols, for the reaction.

[4]

31(a) Alkanes are saturated hydrocarbons with the general formula CnH2n+2.

A student carries out an experiment to measure the enthalpy change of combustion, ΔcH, of hexane.

The student finds that combustion of 1.29 g of hexane changes the temperature of 200 g of water from 20.5 °C
to 65.5 °C.

(i) Calculate the enthalpy change of combustion, ΔcH, of hexane, in kJ mol−1.

Give your final answer to an appropriate number of significant figures.

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ΔcH _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ kJ mol−1 [4]

(ii) The calculated value of ΔcH for hexane from this experiment is different from the data book value.

Suggest two reasons for this difference.

[2]

(b) Data book values for the standard enthalpy changes of combustion, ∆cHθ , of the first four alkanes are shown in
the table.

Alkane methane ethane propane butane

∆cHθ / kJ mol−1 –890 –1560 –2219 –2877

(i) The values for the first three alkanes are plotted on the graph below.

Plot the value for butane on the graph.

(ii) Use the graph to estimate the energy released during complete combustion of 1.80 g of pentane.

Show relevant working below and on the graph.

energy released = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ kJ [3]

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(c) The equation for the complete combustion of cyclohexane is shown below.

C6H12(l) + 9O2(g) → 6CO2(g) + 6H2O(l)

Standard enthalpy changes of formation, ∆fHθ , are shown in the table.

Substance C6H12(l) CO2 (g) H2O(l)

∆fHθ / kJ mol−1 –156.3 –393.5 – 285.8

Calculate the standard enthalpy change of combustion, ∆cHθ , of cyclohexane.

∆cHθ = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ kJ mol−1 [3]

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32 The hydroxyl group, –OH, is responsible for many properties of alcohols.

Methanol, CH3OH, is soluble in water because it has polar bonds.

Pauling electronegativity values for carbon, oxygen and hydrogen are shown below.

Element Electronegativity
Carbon 2.5
Oxygen 3.5
Hydrogen 2.1

Use a labelled diagram to explain why methanol is soluble in water.

• Use displayed formulae showing one molecule of methanol and one molecule of water.
• Add partial charges δ+ and δ – to show the two most polar bonds in a methanol molecule and the polar
bonds in a water molecule.
• Show all lone pairs.
• Label the most important intermolecular bond between the molecules.

[2]

33(a) Propanoic acid, CH3CH2COOH, is a member of the homologous series of carboxylic acids.

Suggest the general formula for a carboxylic acid.

[1]

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(b) The displayed formula for propanoic acid is shown below.

(i) State the shape and bond angle around a carbon atom in the alkyl group of propanoic acid. Explain the
shape.

Shape

Bond angle

Explanation

[2]

(ii) Suggest a value for the C–O–H bond angle in propanoic acid.

[1]

(c) 2-Chloropropanoic acid, CH3CHClCOOH, can be made by reacting propanoic acid with chlorine in a radical
substitution reaction.

(i) State the conditions for the reaction.

[1]

(ii) Write the overall equation for the reaction.

[1]

(iii) The first step in the reaction mechanism involves homolytic fission of a chlorine molecule to form two chlorine
radicals.

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Why is this step an example of homolytic fission?

[1]

(iv) Write two equations to show the propagation steps in the mechanism for this reaction.

Use dots,•, to show the unpaired electrons on radicals.

[2]

(v) Draw the displayed formula of the radical formed in the first propagation step.

Use a dot,•, to show the position of the unpaired electron.

[1]

(vi) Further substitution forms a mixture of organic products.

Draw the structure of an organic product formed from 2-chloropropanoic acid by further substitution.

[1]

34(a) Organic compounds can be prepared in the laboratory using synthetic routes with two or more stages.

A student devises a two-stage synthesis of cyclohexene from bromocyclohexane.

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(i) Suggest the structure of intermediate E and the reagent(s) and conditions for step 2.

reagent(s) and conditions [2]

(ii) The student carries out this synthesis and obtains 1.23 g of pure cyclohexene from 5.50 g of
bromocyclohexane.

Calculate the percentage yield of cyclohexene.

Give your final answer to an appropriate number of significant figures.

percentage yield = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ % [3]

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(b) Cyclohexene is reacted with bromine to prepare the organic compound F.

Give the structure of compound F and outline the mechanism for this reaction.

Include curly arrows, charges and relevant dipoles.

[4]

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35(a) Bromine is a reactive element. It combines with other non-metals to form covalent compounds.
Phosphorus tribromide, PBr3, and iodine monobromide, IBr, are examples of covalent compounds used in
organic synthesis.

PBr3 can be prepared by heating bromine with phosphorus, P4.

(i) Write an equation for this reaction.

[1]

(ii) How many molecules are present in 1.3535 g of PBr3?

number of molecules = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]

(iii) The ‘dot-and-cross’ diagram of a molecule of PBr3 is given below.

Name the shape of this molecule and explain why the molecule has this shape.

name:

explanation:

[3]

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(b) Bromine reacts with iodine to form iodine monobromide, IBr.

The table below lists some average bond enthalpies which are required in different parts of this question.

Bond Average bond enthalpy / kJ mol–1

Br–Br +193
I–I +151
I–Br +175

(i) Average bond enthalpy is the enthalpy change for the breaking of 1 mole of bonds in gaseous molecules.

Why do Br2 and I2 not exist in the gaseous state under standard conditions?

[1]

(ii) Calculate the enthalpy change of formation, △fH, for IBr.

ΔfH= _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ kJ mol–1 [2]

(c) Iodine monobromide, I–Br, is a polar molecule.

Heterolytic fission of the I–Br bond forms an electrophile.

State the meaning of the term electrophile and suggest the formula of the electrophile formed from IBr.

[2]
(d) Bromine disproportionates when it reacts with potassium hydroxide solution.

Suggest an equation for this reaction.

[1]

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36(a) A large proportion of the world’s output of organic chemicals is used to make addition polymers. These polymers
have a variety of uses.

Poly(propene) is used to make packaging, textiles and rope.

A repeat unit for poly(propene) is shown below.

(i) Explain why poly(propene) is a saturated hydrocarbon.

[1]

(ii) State the bond angle around each carbon atom in poly(propene).

[1]

(iii) After polymers have been used for packaging, the waste polymers need to be processed to save resources,
for example, by recycling.

Describe two other ways in which waste poly(propene) can be processed in a sustainable way.

[2]

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(b) Poly(ethenol) is used to make soluble laundry bags.

A section of the structure of poly(ethenol) is shown below.

(i) Draw a structure to represent one repeat unit of poly(ethenol).

[1]

(ii) Poly(ethenol) is not manufactured from ethenol.

Ethenol is unstable and it forms a more stable structural isomer.

Analysis of the structural isomer gave the following data.

Infrared spectrum

Mass spectrum

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Use all the data to show that the isomer is not ethenol.

Identify the structural isomer of ethenol.

In your answer you should make clear how your explanation is linked to the evidence.

[4]

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37(a) Nitrogen can be reacted with hydrogen in the presence of a catalyst to make ammonia in the Haber process.

N2(g) + 3H2(g) ⇌ 2NH3(g) ΔH = –92 kJ mol–1

Describe and explain the effect of increasing the pressure on the rate of this reaction.

[2]
(b) A mixture of N2 and H2 was left to react until it reached equilibrium. The equilibrium mixture had the following
composition:

N2 1.20 mol dm–3

H2 2.00 mol dm–3
NH3 0.877 mol dm–3

(i) Calculate a value for Kc for this equilibrium.

Kc = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ dm6 mol–2 [3]

(ii) Explain how the following changes would affect the amount of NH3 present in the equilibrium mixture.

Use of a catalyst:

A higher temperature:

[3]

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(c) of ammonia from the Haber process is reacted with carbon dioxide to prepare the fertiliser urea, NH2CONH2.

2NH3(g) + CO2(g) → NH2CONH2(s) + H2O(1)

1.35 tonnes of urea are formed.

Calculate the percentage yield of urea.

Show all your working.

yield = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ % [3]

38(a) Students work together in groups to identify four different solutions.

Each solution contains one of the following compounds:

ammonium sulfate, (NH4)2SO4

sodium sulfate, Na2SO4
sodium chloride, NaCl
potassium bromide, KBr.

Your group has been provided with universal indicator paper and the following test reagents:

barium chloride solution

silver nitrate solution
dilute ammonia solution
sodium hydroxide solution.

* A student in your group suggests the following plan:

Add about 1 cm depth of each solution into separate test-tubes.

Add a few drops of barium chloride solution to each test-tube.
A white precipitate will show which solutions contain sulfate ions.
Two of the solutions will form a white precipitate.

Describe how you would expand this plan so that all four solutions could be identified using a positive test result.

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You should provide observations and conclusions that would enable your group to identify all four solutions.

[6]
(b) Solid barium chloride has a high melting point. Barium chloride dissolves in water to form a solution that can be
used to test for sulfate ions.

(i) Draw a ‘dot-and-cross’ diagram to show the bonding in solid barium chloride.
Show outer electrons only.

[2]

(ii) A solution of barium chloride can be made in the laboratory using dilute hydrochloric acid.

Suggest a compound that can be reacted with hydrochloric acid to make barium chloride.

[1]

Pentan-2-ol can be prepared by the alkaline hydrolysis of 2-iodopentane.

CH3CH(I)CH2CH2CH3 + NaOH → CH3CH(OH)CH2CH2CH3 + NaI

The reaction mixture is boiled for 20 minutes.

(i) State the most appropriate technique that could be used to boil the reaction mixture for 20 minutes.

[1]

(ii) Describe the mechanism for the alkaline hydrolysis of 2-iodopentane.

In your answer, include the name of the mechanism, curly arrows and relevant dipoles.

name of mechanism: _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

[4]

(b) Alcohols can be converted into haloalkanes in a substitution reaction.

Plan an experiment to prepare approximately 0.1 mol of 2-bromopentane,

CH3CHBrCH2CH2CH3, from pentan-2-ol, CH3CH(OH)CH2CH2CH3.

Your plan should include a calculation of the mass of alcohol required and details of the chemicals to be used in
the reaction.

[2]

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(c) * Alcohols can be converted into alkenes in an elimination reaction.

The elimination of H2O from pentan-2-ol forms a mixture of organic products.

Give the names and structures of all the organic products in the mixture.

Your answer should explain how the reaction leads to the different isomers.

[6]

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40 A student carries out an experiment to identify an unknown carbonate.

The student weighs a sample of the solid carbonate in a weighing bottle.

The student tips the carbonate into a beaker and weighs the empty weighing bottle.
The student prepares a 250.0 cm3 solution of the carbonate.
The student carries out a titration using 25.0 cm3 of this solution measured using a pipette with 0.100 mol
dm–3 hydrochloric acid in the burette.

The sample of carbonate is dissolved in approximately 100 cm3 of distilled water in a beaker and the solution
transferred to a volumetric flask. The volume of the solution is made up to 250.0 cm3 with distilled water.

Another student suggests two possible sources of error:

A small amount of solid remained in the weighing bottle.

A small amount of solution remained in the beaker.

State whether the other student’s statements are correct.

How could the procedure be improved?

[2]

41(a) Sodium hydroxide is an alkali.

What is meant by the term alkali?

[1]

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(b) A student carries out a titration to determine the molar mass and structure of a weak acid A.

The student follows the method below.

• Dissolve a weighed mass of A in 100 cm3 of distilled water and make the solution up to 250 cm3 in a
beaker.

• Add the solution of A to a burette.

• Titrate the solution of A with a standard solution of sodium hydroxide, NaOH.

What is meant by the term standard solution?

[1]

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42(a) A student carries out an experiment to identify an unknown carbonate.

The student weighs a sample of the solid carbonate in a weighing bottle.

The student carries out the final part of the experiment by adding 0.100 mol dm–3 hydrochloric acid to a burette
and performing a titration using a 25.0 cm3 sample of the aqueous carbonate.

The student reads the burette to the nearest 0.05 cm3.

The diagrams below show the initial burette reading and the final burette reading.

(i) Record the student’s readings and the titre.

[1]

(ii) Describe what the student should do next to obtain reliable results for the titration.

[1]

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(b) The equation below represents the reaction between the carbonate and hydrochloric acid.

M2CO3(aq) + 2HCl(aq) → 2MCl(aq) + CO2(g) + H2O(l)

(i) Calculate the amount, in mol, of M2CO3 used in the titration.

n(M2CO3) = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ mol [2]

(ii) The student’s mass readings are recorded below.

Mass of weighing bottle + carbonate / g 14.92

Mass of weighing bottle / g 13.34

Use the student’s results to identify the carbonate, M2CO3.

Show all your working.

[4]

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43(a) A student carries out a titration to determine the molar mass and structure of a weak acid A.

The student follows the method below.

• Dissolve a weighed mass of A in 100 cm3 of distilled water and make the solution up to 250 cm3 in a
beaker.

• Add the solution of A to a burette.

• Titrate the solution of A with a standard solution of sodium hydroxide, NaOH.

The student carries out a trial, followed by three further titrations.

The diagram shows the initial and final burette readings for the three further titrations.

The student measures all burette readings to the nearest 0.05 cm3.

Titration 1 Titration 2 Titration 3

Initial reading Final reading Initial reading Final reading Initial reading Final reading

(i) Record the student’s readings and the titres in the table below.

Calculate the mean titre, to the nearest 0.05 cm3, that the student should use for analysing the results.

Titration 1 Titration 2 Titration 3

3
Final reading/cm
Initial reading/cm3
Titre/cm3

(ii) The uncertainty in each burette reading is ± 0.05 cm3.

Calculate the percentage uncertainty for the titre in Titration 1.

percentage uncertainty = % [1]

(iii) The student realised that the solution of A had not been prepared correctly.

How should the student have made up the solution?

[1]

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(b) A student repeats the titration to determine the molar mass and structure of A.

• The student prepares a 250.0 cm3 solution from 1.513 g of A.

• The solution of A is added to the burette and titrated with 25.0 cm3 volumes of 0.112 mol dm−3 NaOH(aq).

• 1 mol of A reacts with 2 mol of NaOH.

• The student obtains a mean titre of 27.30 cm3.

(i) Calculate the molar mass of A from these results.

Give your answer to the nearest whole number.

Show your working.

molar mass of A = g mol−1 [4]

(ii) A is an organic acid, containing C, H and O only.

One molecule of A contains two COOH groups.

Suggest the structure of A.

[1]

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44(a) Sodium sulfide, Na2S, is an ionic compound of sodium, Na, and sulfur, S.

Draw a ‘dot-and-cross’ diagram to show the bonding in sodium sulfide.

Show outer electrons only.

[2]
(b) The table below compares the properties of sodium sulfide, sodium and sulfur.

Complete the table.

Sodium sulfide Sodium Sulfur

Melting point / °C 1180 98 113

Type of structure
(giant or simple)

solid
Electrical conductivity liquid
(good or poor)

[3]

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(c) Selenium is in the same group of the periodic table as sulfur.

(i) Complete the full electron configuration of a selenium atom.

1s2 [1]

(ii) Sodium selenide reacts with hydrochloric acid to form a toxic gas, B, with a relative molecular mass of 81.0.

Identify gas B and write an equation for this reaction.

Gas B

Equation [2]

Bromine is used to extract iodine from a solution containing iodide ions.

(i) Write an ionic equation for the reaction.

[1]

(ii) Explain why iodine is less reactive than bromine.

[3]

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(b) Iodine can be used for the small-scale purification of drinking water.

(i) Iodine reacts with water as shown below.

I2 + H2O ⇌ HI + HIO

Using oxidation numbers, explain why this reaction is a disproportionation.

[3]

(ii) Chlorine is used to purify water on a large scale.

State one disadvantage of using chlorine for the purification of drinking water.

[1]

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(c) Hydrogen reacts with chlorine to form hydrogen chloride, HCl:

H2(g) + Cl2(g) → 2HCl(g) ΔH = −184 kJ mol−1

Table 3.1 shows bond enthalpies.

Bond Bond Enthalpy / kJ mol−1

H−H +436
Cl−Cl +243

Table 3.1

Calculate the bond enthalpy for the H–Cl bond from the information above.

bond enthalpy = kJ mol−1 [2]

(d) ‘Enthalpy change of vaporisation’ is the enthalpy change when one mole of a substance changes from a liquid to
a gas at its boiling point.

(i) Write an equation, including state symbols, to represent the enthalpy change of vaporisation of bromine.

[1]

(ii) Suggest whether the enthalpy change of vaporisation of bromine is exothermic or endothermic.

Explain your answer.

[1]

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46(a) The reaction of ammonia, NH3, with oxygen to form nitrogen monoxide, NO, is an important industrial process.

The equation for this reaction is shown in equilibrium 4.1 below.

4NH3(g) + 5O2(g) ⇌ 4NO(g) + 6H2O(g) ΔH = −905 kJ mol−1 Equilibrium 4.1

The forward reaction in equilibrium 4.1 converts NH3 into NO.

(i) Complete the enthalpy profile diagram for this reaction.

On your diagram:
• Label the activation energy, Ea
• Label the enthalpy change of reaction, ΔH
• Include the formulae of the reactants and products.

[2]

Calculate the energy released, in kJ, for this conversion.

Give your answer in standard form and to an appropriate number of significant figures.

energy released = kJ [4]

(b) Write an expression for the equilibrium constant, Kc, in equilibrium 4.1.

[1]

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(c) Predict the conditions of temperature and pressure for a maximum equilibrium yield of nitrogen monoxide in
equilibrium 4.1.

• Explain your prediction in terms of le Chatelier’s principle.

• State and explain how these conditions could be changed to achieve a compromise between equilibrium
yield, rate and other operational factors.

[5]

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47
A student investigates the rate of reaction of 1-bromobutane with aqueous hydroxide ions.

The graph shows how the hydroxide ion concentration, [OH−(aq)], changes during the reaction.

Using the graph, calculate the rate of reaction, in mol dm−3 min−1, at 30 minutes.

Show your working on the graph and in the space below.

rate of reaction = mol dm−3 min−1 [2]

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48(a) Two reactions of compound C are shown in the flowchart below.

State the reagents and conditions for reaction 1.

[1]

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(b) In reaction 2, compound C reacts with bromine to form compound D.

(i) Give the systematic name of compound D.

[1]

(ii) Outline the mechanism for reaction 2.

Include curly arrows, charges and relevant dipoles.

[3]

(i) Write a balanced equation for this reaction.

Show displayed formulae.

[2]

(ii) State one advantage and one disadvantage of using combustion as a method for the disposal of waste
polymer E.

Advantage

Disadvantage

[2]

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49(a) This question is about the properties and reactions of the Group 2 element strontium.

The relative atomic mass of strontium can be determined using a mass spectrometer.

(i) Explain what is meant by the term relative atomic mass of an element.

[2]

(ii) A sample of strontium has a relative atomic mass of 87.73.

The sample consists of:

• 82.9% Sr-88
• 6.9% Sr-87
• one other isotope.
Determine the other isotope of strontium in the sample.

isotope of strontium = ...................................................... [2]

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(b) The table below shows two physical properties of the element strontium.

Melting point high

Electrical conductivity very good

Explain these physical properties of strontium, in terms of bonding and structure.

Include a labelled diagram in your answer.

Diagram

Explanation

[5]

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(c) A student adds a small amount of strontium to water.

When the reaction has finished, the student measures the pH of the final solution.

(i) Write the equation for the reaction of strontium with water.

[1]

(ii) Describe two observations which would be different if the student had used calcium in place of strontium.

[2]
(d) When hydrated strontium chloride is heated, the water of crystallisation is removed, leaving a residue of
anhydrous strontium chloride.

A student carries out an experiment to find the value of x in the formula of hydrated strontium chloride,
SrCl2•xH2O.

The student’s method is outlined below.

Step 1
Weigh an empty crucible.
Add SrCl2•xH2O to the crucible and reweigh.

Step 2
Heat the crucible and contents for 10 minutes.
Allow to cool and reweigh.

Step 3
Heat the crucible and residue for another 5 minutes.
Allow to cool and weigh the crucible and residue.

Repeat step 3 a further two times.

The student’s results are shown below:

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Mass of empty crucible / g 15.96
Mass of crucible + SrCl2•xH2O / g 18.65
First mass of crucible + residue / g 17.66
Second mass of crucible + residue / g 17.61
Third mass of crucible + residue / g 17.58
Fourth mass of crucible + residue / g 17.58

(i) Calculate the value of x in SrCl2•xH2O.

Give your answer to 2 significant figures.

x = ...................................................... [3]

(ii) Suggest why the student takes four readings of the mass of the crucible and residue.

[1]

(iii) Suggest two modifications to the method that would reduce the percentage uncertainty in the mass of the
residue.

[2]

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50(a) A solution of magnesium nitrate can be prepared by reacting magnesium carbonate, MgCO3,with nitric acid,
HNO3(aq).

The equation is shown below.

MgCO3(s) + 2HNO3(aq) → Mg(NO3)2(aq) + H2O(l) + CO2(g)

Calculate the minimum volume, in cm3, of 1.75 mol dm–3 HNO3 that is needed to prepare a solution containing
5.00 g of Mg(NO3)2.

Give your answer to 3 significant figures.

volume =......................................................cm3 [3]

(b) Magnesium nitrate decomposes when heated, as shown in the equation.

2Mg(NO3)2(s) → 2MgO(s) + 4NO2(g) + O2(g)

Using oxidation numbers, show which element has been oxidised and which has been reduced when
magnesium nitrate decomposes.

State the changes in oxidation numbers, including all signs.

Element oxidised ......................................................

Oxidation number change: from ............. to .............

Element reduced ......................................................

Oxidation number change: from ............. to .............

[2]

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51(a) This question is about 1-iodopentane, CH3CH2CH2CH2CH2I.

1-Iodopentane can be hydrolysed by aqueous sodium hydroxide.

(i) Outline the mechanism for this reaction.

Include curly arrows, relevant dipoles and the final product(s).

[3]

(ii) 1-Iodopentane can also be hydrolysed by water using aqueous silver nitrate, with ethanol as the solvent.

A student uses this method to compare the rates of hydrolysis of 1-iodopentane and 1-bromopentane.

What measurement and observation would allow the student to compare the rates of hydrolysis?

[1]

(iii) 1-Iodopentane was found to react faster than 1-bromopentane.

Explain why.

[2]

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(b) The mass spectrum of 1-iodopentane is shown below.

(i) What information is given by the peak labelled X (m/z = 198)?

[1]

(ii) Write the structural formulae of the ions responsible for the peaks labelled Y and Z.

Y (m/z = 71)

Z (m/z = 43) [2]

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(c) 2-Iodo-2-methylbutane is an isomer of 1-iodopentane.

(i) Draw the structure of 2-iodo-2-methylbutane.

[1]

(ii) Suggest one similarity and one difference between the mass spectra of 1-iodopentane and
2-iodo-2-methylbutane.

Similarity

Difference

[2]

52(a) Zinc reacts with hydrochloric acid, HCl(aq), as shown in the following equation.

Zn(s) + 2HCl(aq) → ZnCl2(aq) + H2(g)

A student investigates the rate of this reaction.

The student plans to react 50.0 cm3 of 0.100 mol dm–3 HCl with 0.200 g of zinc (an excess).

Calculate the volume, in cm3, of hydrogen that should be produced at RTP.

volume = ..................................................... cm3 [3]

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(b) The student uses the apparatus in the diagram.

The student’s method is outlined below:

• Pour 50.0 cm3 of 0.100 mol dm–3 HCl into the conical flask.
• Add 0.200 g of zinc (an excess), and quickly attach the delivery tube and gas syringe.
• Measure the volume of gas collected every 20 seconds until the reaction stops.

The student obtains the results shown in Table 4.1.

Time / s 0 20 40 60 80 100 120 160 200

Volume of gas / cm3 0 16 27 37 39 50 53 58 58
Table 4.1

(i) On the graph paper in Fig. 4.1, label the x axis and plot the results in Table 4.1. [1]

(ii) Circle any anomalous results present in the graph you have drawn in Fig. 4.1. [1]

(iii) Draw a best-fit smooth curve on the graph you have drawn in Fig. 4.1. [1]

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(c) The student repeats the experiment using:

• zinc with the same mass (0.200 g) and same surface area
• the same temperature and pressure
• 40.0 cm3 of 0.125 mol dm–3 HCl, instead of 50.0 cm3 of 0.100 mol dm–3 HCl.

On your graph in Fig. 4.1 sketch the curve you would expect in this experiment. [2]
(d) The graph shows that rate of reaction decreases over time.

Explain why, in terms of collision theory.

[2]

(i) The rate of the reaction between zinc and hydrochloric acid can be increased using a solution of copper(II)
sulfate as a catalyst.

Explain how a catalyst increases the rate of reaction.

[2]

(ii) Why is it difficult to classify the solution of copper(II) sulfate as a homogeneous or heterogeneous catalyst in
this reaction?

[1]

53 This question is about hex-1-ene, CH3CH2CH2CH2CH=CH2.

Hex-1-ene is reacted with H2, HCl and Br2 as shown in the flowchart below.

(i) Complete the flowchart to show the structures of the organic products of these reactions.

(ii) State the catalyst needed in reaction 1.

[1]

(iii) What would you observe in reaction 3?

[1]

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54(a) This question is about nickel and its compounds.

Nickel reacts with dilute hydrochloric acid in a redox reaction.

Ni(s) + 2HCl (aq) NiCl 2(aq) + H2(g)

Explain, in terms of the number of electrons transferred, whether nickel is oxidised or reduced.

[1]

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(b) A student completely reacts 0.192 g of nickel with 0.150 mol dm–3 HCl(aq).

(i) Calculate the minimum volume, in cm3, of 0.150 mol dm–3 HCl(aq) that the student needs for the reaction.

Give your answer to 3 significant figures.

minimum volume of HCl(aq) = .................................................. cm3 [3]

(ii) Calculate the volume of H2(g), in cm3, that would be produced at RTP.

volume of H2(g) = .................................................. cm3 [1]

(iii) The student repeats the experiment with 0.192 g of magnesium instead of nickel, using the same volume of
0.150 mol dm–3 HCl(aq) as in (i).

State and explain whether the volume of H2(g) produced would be greater than, smaller than, or the same
as, the value you have calculated in (ii).

[2]

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55(a) Enthalpy changes of combustion can be determined directly by experiment.

Explain the term enthalpy change of combustion, Δc H.

[2]

(b) A student carries out an experiment to determine the enthalpy change of combustion of cyclohexane, C6H12,
using the apparatus shown in the diagram.

In the experiment, 0.525 g of cyclohexane are burnt, and the temperature of the 200 cm3 of water changes from
21.0 °C to 41.0 °C.

Calculate the enthalpy change of combustion, Δc H, of cyclohexane in kJ mol–1.

Give your answer to 3 significant figures.

Δc H = ............................................ kJ mol–1 [4]

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(c) The student finds that their experimental value for Δc H is less exothermic than the value in a data book.

The student evaluates the experimental results.

(i) The uncertainty in each thermometer reading is ±0.5 °C and the uncertainty in the measured volume of water
is ±2 cm3.

Determine whether the temperature change or the measured volume of water has the greater percentage
uncertainty.

[2]

(ii) Suggest two reasons, apart from measurement uncertainties, why the experimental value for Δc H is less
exothermic than the data book value.

Reason 1

Reason 2

[2]

(iii) In the experiment the water in the beaker was heated for 5 minutes. The student thought that the experiment
could be improved by heating the water for 10 minutes.

Explain whether the accuracy in the student’s calculated value for Δc H may or may not be improved by
heating for longer.

56(a) This question is about some elements in Period 4 of the periodic table.

The table shows the melting point and electrical conductivity of two elements in Period 4.

Element Melting Point / °C Electrical conductivity

Calcium 842 Good
Bromine –7 Poor

Use your knowledge of structure and bonding to explain the properties in the table.

[5]

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(b) Calcium reacts with bromine to form calcium bromide, CaBr2.

(i) Draw a ‘dot-and-cross’ diagram to show the bonding in CaBr2.

Show outer electrons only.

[2]

(ii) The reaction of barium with bromine is more vigorous than the reaction of calcium with bromine.

Explain why.

[3]

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(c) The Period 4 element selenium is in the same group of the periodic table as oxygen.

Selenium and oxygen both form compounds with hydrogen with the formulae H2Se and H2O respectively.

(i) H2Se can be prepared by reacting aluminium selenide, Al 2Se3, with water.
Aluminium hydroxide and hydrogen selenide are formed.

Write the equation for this reaction.

[1]

(ii) The boiling points of H2O and H2Se are shown below.

Compound Boiling point / °C

H2O 100
H2Se –41

Explain why H2O has a higher boiling point than H2Se.

[3]

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(d) Bromine reacts with concentrated sodium hydroxide at 50 °C as in the equation below.

3Br2 + 6NaOH 5NaBr + NaBrO3 + 3H2O

(i) Write the systematic name for NaBrO3.

[1]

(ii) This reaction is an example of disproportionation.

Use oxidation numbers to explain why. Include the meaning of the term disproportionation.

[3]

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57(a) Nitrosyl chloride, NOCl , is used in the industrial manufacture of nylon.

The ‘dot-and-cross’ diagram for nitrosyl chloride is shown below.

Predict the O=N–Cl bond angle and explain why NOCl has this bond angle.

Bond angle

Explanation

[3]

(b) Nitrosyl chloride, NOCl, dissociates into nitrogen monoxide and chlorine as in the equilibrium below.

2NOCl(g) 2NO(g) + Cl 2(g) ΔH = +77.0kJmol–1

Nitrosyl chloride is added to a container, which is then sealed.

The container is heated to 400 °C, and equilibrium is allowed to be reached.

(i) Write the expression for the equilibrium constant, Kc, for this equilibrium.

[1]

(ii) In the equilibrium mixture at 400 °C, the equilibrium concentration of Cl2(g) is found to be 0.17 mol dm–3.

The student calculates that the equilibrium concentration of NO(g) is 0.34 mol dm–3.

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Explain how the student obtained this value for [NO(g)].

[1]

(iii) At 400 °C, Kc = 0.015 moldm–3.

Calculate the equilibrium concentration of NOCl(g) at 400°C.

equilibrium concentration of NOCl(g) = .......................................... mol dm–3 [2]

(iv) The temperature of the equilibrium mixture is increased above 400 °C while keeping the pressure constant.

State and explain the effect on the equilibrium concentration of nitrogen monoxide, NO(g), with these new
conditions.

[2]

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58(a) This question is about the alcohols A–F shown below.

Which of the alcohols A–F are secondary alcohols?

[2]

(b) Complete a balanced equation for the complete combustion of alcohol C.

CH3CH2CH(OH)CH3 + ......................................... → ......................................... + ....................................... [1]

[1]

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(d) Alcohol A can be prepared by the alkaline hydrolysis of the bromoalkane, (CH3)2CHCH2CH2Br.
The hydrolysis with aqueous NaOH is shown in equation 5.1.

(CH3)2CHCH2CH2Br + NaOH → (CH3)2CHCH2CH2OH + NaBr equation 5.1

alcohol A

A student gently heats a mixture of (CH3)2CHCH2CH2Br and NaOH(aq) for 25 minutes.

(i) Calculate the atom economy for the preparation of alcohol A in equation 5.1.

atom economy = ..................................................... % [2]

(ii) Outline the mechanism for the alkaline hydrolysis of (CH3)2CHCH2CH2Br.

The structure of (CH3)2CHCH2CH2Br has been provided.

Show curly arrows, relevant lone pairs and dipoles, and the products.

[3]

(iii) Name this type of mechanism.

[1]

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(e) The student decides to prepare alcohol A using the same method as in the part above but using the chloroalkane
(CH3)2CHCH2CH2Cl instead of the bromoalkane, (CH3)2CHCH2CH2Br.

State and explain how the rates of hydrolysis of the chloroalkane and the bromoalkane would differ.

[2]

59(a) This question is about compounds of sulfur.

Potassium sulfide, K2S, shows ionic bonding.

(i) Explain what is meant by ionic bonding.

[1]

(ii) Draw a ‘dot-and-cross’ diagram to show the bonding in K2S.

Show outer electrons only.

[2]

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(b) Sulfur difluoride, SF2, shows covalent bonding.
Draw a ‘dot-and-cross’ diagram to show the bonding in SF2.
Show outer electrons only.

[2]
(c) At room temperature, K2S is a solid, but SF2 is a gas.

Use ideas about structure and bonding to explain this difference.

[3]

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(d) Sulfur hexafluoride, SF6, is used in medical ultrasound imaging because SF6 is unreactive.

(i) State the shape of, and F—S—F bond angle in, an SF6 molecule.

Shape .............................................................................................

Bond angle ......................................................................................

[2]

(ii) Suggest why SF6 is unreactive.

[1]

60(a) Glutaric acid is used in the production of polymers.

The formula of glutaric acid can be represented as HOOC(CH2) n COOH, where n is a whole number.

A student carries out a titration to find the value of n.

1. The student dissolves 2.891 g of glutaric acid in water and makes up the solution to 250.0 cm3 in a
volumetric flask.
2. The student transfers 25.0 cm3 of this solution into a conical flask.
3. The student titrates the solution with 0.240 mol dm–3 NaOH(aq) in the burette.
Equation:
HOOC(CH2) n COOH(aq) + 2NaOH(aq) → NaOOC(CH2) n COONa(aq) + 2H2O(l)

The student uses phenolphthalein as the indicator.

Phenolphthalein is colourless in acid and pink in alkali.

State the colour change observed at the end point of the titration.

Colour from ....................................................... to ....................................................... [1]

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(b) The student carries out a trial titration followed by three further titrations, 1, 2 and 3.

The results are shown in the table below.

Titration Trial 1 2 3
3
Final reading / cm 18.70 36.55 18.30 36.60
3
Initial reading / cm 0.20 18.50 0.10 18.30
3
Titre / cm

[1]

(i) Complete the table to show the titre in each titration.

[1]

(ii) Why does the student carry out a trial titration?

[1]

(iii) Calculate the mean titre of NaOH(aq) that the student should use for analysing the results.

mean titre = .................................................. cm3 [1]

(iv) In the titration, the uncertainty in each burette reading is ± 0.05 cm3.

Calculate the percentage uncertainty in the titre for Titration 1.

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percentage uncertainty = ..................................................... % [1]

(c) Calculate the value of n in HOOC(CH2) n COOH.

Give your answer to the nearest whole number.

n = .......................................................... [5]

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(d) A 25.0 cm3 pipette was used to measure out the 25.0 cm3 of glutaric acid solution for each titration.

Before use, one student washed the pipette out with water instead of the glutaric acid solution.

State the effect of this mistake on the titre.

Explain your answer.

Effect

Explanation

[2]

61(a) Methanol, CH3OH, is manufactured by the reaction of carbon monoxide, CO, with hydrogen, H2.

CO(g) + 2H2(g) ⇌ CH3OH(g) ΔH = –91 kJ mol–1

Write the expression for the equilibrium constant, Kc, for this equilibrium.

[1]

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(b) A chemist mixes CO and H2 in a container.
The mixture is heated to 200 °C and left to reach equilibrium.

The equilibrium concentrations of CO and H2 are shown in the table.

Compound Equilibrium concentration / mol dm–3

CO(g) 0.57
H2(g) 0.40

The numerical value of Kc for this equilibrium is 15.4.

(i) Calculate the equilibrium concentration of CH3OH(g).

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

(ii) What does the numerical value of Kc tell you about the position of equilibrium?

[1]

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(c) The industrial manufacture of methanol has used a copper-based catalyst.

Chemists have recently developed a new method for making methanol that uses a nickel-gallium catalyst. This
allows methanol to be produced at a lower temperature than the old method.

Suggest two reasons why using a lower temperature is beneficial to the environment.

[2]
(d) Nickel and gallium are in period 4 of the periodic table.

(i) Which block in the periodic table does nickel belong to?

[1]

(ii) Complete the electron configuration of gallium.

1s2

[1]

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(e) Element A is in period 3 of the periodic table (Na-Ar).

The first six ionisation energies (I.E.) of element A are shown below.

1st I.E. / kJ 2nd I.E. / kJ 3rd I.E. / kJ 4th I.E. / kJ 5th I.E. / kJ 6th I.E. / kJ
–1 –1 –1 –1 –1
mol mol mol mol mol mol–1
789 1577 3232 4356 16091 19785

Identify element A.

Explain your answer.

Element A =

Explanation

[2]

62(a) A student investigates the rate of reaction between strontium and water.

Sr(s) + 2H2O(l) → Sr(OH)2(aq) + H2(g)

The student’s method is shown below.

• Pour 100 cm3 of water into a conical flask.
• Add 0.26 g of strontium and quickly connect a 100 cm3 gas syringe.
• Measure the volume of gas produced every 10 seconds until all the strontium has reacted.

The student plots a graph of volume of gas produced against time as shown in Fig. 6.1.

Draw a best fit curve on Fig. 6.1.

Use the graph to determine the rate of reaction, in cm3 s–1, at 50 s.

Show your working below and on the graph.

rate at 50 s ............................................. cm3 s–1 [3]

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(b) A second student suggests that the experiment could be improved by measuring the loss in mass in the conical
flask over time.

The student places a conical flask containing 100 cm3 of water on a 2 decimal place balance, and then adds
0.26 g of strontium.

The mass is recorded every 10 seconds.

Suggest one advantage and one disadvantage of using this method compared to the gas collection method.

Advantage:

Disadvantag

[2]

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(c) A third student repeats the original experiment using the same amount, in moles, of barium as strontium.

(i) Calculate the mass of barium that the student uses.

Give your answer to 2 decimal places.

mass of barium = ...................................................... g [2]

(ii) The student observes that the rate of reaction for barium is different from the rate of reaction with
strontium.

On Fig. 6.1 sketch the graph the student would obtain using barium instead of strontium.
[2]

(iii) Describe and explain the difference in reactivity of barium and strontium with water.

[4]

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63(a) 2-Chloro-2-methylpropane, (CH3)3CCl , is an organic liquid with a boiling point of 50 °C.

A student prepares (CH3)3CCl by reacting 2-methylpropan-2-ol, (CH3)3COH, with concentrated hydrochloric acid.

Write a balanced equation for this reaction.

Use skeletal formulae for organic compounds.

[2]

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(b) Compounds A and B are structural isomers of (CH3)3COH.

(i) Compound A is a secondary alcohol.

What is the systematic name of compound A?

[1]

(ii) Compound B is a branched primary alcohol.

Compound B is refluxed with acidified potassium dichromate(VI) as an oxidising agent.

Write the equation for the reaction that takes place.

Use structures for organic compounds and [O] for the oxidising agent.

[3]

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64(a) Alkane A, shown below, reacts with bromine in a radical substitution reaction.

Alkane A

What is meant by a radical?

[1]
(b) Name the type of bond breaking that occurs in a radical substitution reaction.

[1]
(c) In this reaction with bromine, monosubstitution of alkane A forms a mixture of organic products.

Show the structures of two monosubstituted organic products that are formed.

[2]
(d) With excess bromine, further substitution takes place.

Write an equation for the reaction of alkane A with excess bromine to produce 1,3-dibromo-2-methylpropane.

Use structures for the organic compounds.

[2]

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65(a) Lime is a citrus fruit containing citric acid, C6H8O7.

Citric acid is a weak organic acid.

(i) What is meant by an acid?

[1]

(ii) What is meant by an acid that is weak?

[1]

(b) A student carries out a titration to determine the mass of citric acid in a lime.
The student follows the method below:
• Squeeze the juice out of two limes.
• Transfer the juice into a 250.0cm3 volumetric flask and make up to the mark with distilled water.
• Pipette 25.0cm3 of the diluted lime juice into a conical flask and add a few drops of phenolphthalein
indicator.
• Titrate this solution with 0.800 mol dm–3 NaOH(aq).

The student carries out a trial titration, followed by three further titrations.

The diagram shows the burette readings for the three further titrations.
Each reading is measured to the nearest 0.05 cm3.

(i) Record the student’s burette readings in the table below.

Calculate the mean titre, to the nearest 0.05 cm3, that the student should use to analyse the results.

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Titration 1 Titration 2 Titration 3
3
Final reading/cm
Initial reading/cm3
Titre/cm3

mean titre .................................................. cm3 [4]

(ii) Citric acid, C6H8O7, is neutralised by NaOH as shown in the equation below.

C6H8O7 + 3NaOH→Na3C6H5O7 + 3H2O

Calculate the mass, in g, of citric acid in one lime.

Assume that citric acid (M r = 192.0) is the only acid in lime juice.

mass of citric acid in one lime = ...................................................... g [5]

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(c) The student’s teacher thinks that there is an unnecessary safety risk in using a sodium hydroxide concentration
of 0.800 mol dm–3 for the titration.

Suggest how the student could modify the method using a sodium hydroxide concentration of 0.200 mol dm–3
instead of 0.800 mol dm–3.

The student should aim to have the same titre as in the original method.

Justify your answer

[2]

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(d) Apple juice contains malic acid which has the following structure.

Malic acid can be oxidised by heating with acidified potassium dichromate(VI).

Write a balanced equation for the reaction, showing the structure of the organic product.

Use [O] to represent the oxidising agent.

[2]

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66(a) This question is about some Group 2 elements and their compounds.

Strontium and calcium both react with water.

(i) Write an equation for the reaction of strontium with water.

[1]

(ii) Using oxidation numbers, explain why the reaction of strontium with water is a redox reaction.

[2]

(iii) Explain why calcium reacts more slowly with water than strontium does.

[3]

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(b) A student adds barium oxide, BaO, to water.

A reaction takes place forming a colourless solution.

(i) Predict the approximate pH of the colourless solution.

pH = ................ [1]

(ii) A student adds a few drops of dilute sulfuric acid to the colourless solution.

Describe what the student would observe, and give the formula of the barium compound produced.

Observation

Formula of barium compound

[2]

67(a) A student investigates some reactions of zinc compounds and zinc metal.

The student investigates the rate of reaction between zinc carbonate, ZnCO3(s), and dilute hydrochloric acid,
HCl(aq).

ZnCO3(s) + 2HCl(aq)→ZnCl 2(aq) + CO2(g) + H2O(l)

The student follows the method outlined below:

• Add 50 cm3 of dilute HCl(aq) into a conical flask at 20°C.

• Place the flask on a top-pan balance.
• Add an excess of ZnCO3(s) to the flask.
• Record the mass of the flask and contents on the top-pan balance every 30 seconds.

The student plots a graph of mass against time, shown in Fig. 3.1 below.

(i) The graph shows that the reaction gets slower over time, and eventually stops.

Explain why, in terms of collision theory.

(ii) Using the graph in Fig. 3.1, find the rate of reaction, in g s–1, at 50 seconds.

Show your working on the graph and in the space below.

rate of reaction = ................................................. g s–1 [2]

(iii) The student repeats the experiment but heats 50 cm3 of dilute hydrochloric acid up to 40°C before adding the
ZnCO3(s).

On Fig. 3.1, sketch the curve the student would obtain. [2]
(b) The student investigates the reaction between zinc and dilute sulfuric acid.

Zn(s) + H2SO4(aq) → ZnSO4(aq) + H2(g) ΔH = –140 kJ mol–1

Copper(II) sulfate is a catalyst for this reaction.

• The student adds a piece of zinc to each of two test tubes.

• The student adds a few drops of aqueous copper(II) sulfate to one of the test tubes, forming a pale blue
solution.
• The student adds an excess of dilute sulfuric acid to each test tube.

(i) Describe two differences the student would observe between the test tubes.

[2]

(ii) Using the axes below, sketch an enthalpy profile diagram for the reaction with and without the catalyst.

On your diagram, include the following labels:

• ΔH, the enthalpy change

• E a, the activation energy without a catalyst
• E c, the activation energy with a catalyst.

[3]

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68(a) This question is about the manufacture of hydrogen, H2.

Hydrogen can be manufactured by reacting ethanol with steam, as shown in Equilibrium 4.2.

Average bond enthalpies are shown in the table below.

Bond C–H C–C C–O O–H H–H C=O

Average bond +415 +347 +358 +464 +435 +805
enthalpy/kJ
mol–1

Calculate ΔH, in kJ mol–1, for the forward reaction in Equilibrium 4.2.

ΔH = ............................................ kJ mol–1 [3]

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(b) CO2 and H2O molecules have different shapes.

State the bond angles in CO2 and H2O molecules and explain, in terms of electron pair repulsion, why the bond
angles are different.

[4]

69(a) 2-Bromobutane, CH3CH2CHBrCH3, can be prepared by several different methods.

The relative molecular mass, M r, of 2-bromobutane is 136.9.

2-Bromobutane can be prepared by reacting butane with bromine (Reaction 5.1).

CH3CH2CH2CH3 + Br2 → CH3CH2CHBrCH3 + HBr Reaction 5.1

The reaction is initiated by the formation of bromine radicals from bromine.

(i) State the conditions for the formation of bromine radicals from bromine.
[1]

(ii) Write two equations for the propagation steps in the mechanism for Reaction 5.1.

Use structural formulae for organic species and dots (·) for unpaired electrons on radicals.

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CH3CH2CH2CH3 + ................ → ......................................... + ................

.................................. + ................ → ......................................... + ................

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

(iii) The yield of CH3CH2CHBrCH3 is only 30%.

Suggest two reasons why the yield of CH3CH2CHBrCH3 is so low.

[2]
(b) 2-Bromobutane can also be prepared by reacting but-2-ene, CH3CH=CHCH3, with hydrogen bromide, HBr
(Reaction 5.2).

CH3CH=CHCH3 + HBr → CH3CH2CHBrCH3 Reaction 5.2

Explain, in terms of atom economy, why Reaction 5.2 is more sustainable than Reaction 5.1.

Include calculations to justify your answer.

[2]

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(c) 2-Bromobutane can be prepared by reacting butan-2-ol, CH3CH2CHOHCH3, with sodium bromide and sulfuric
acid (Reaction 5.3).

CH3CH2CHOHCH3 + H+ + Br– → CH3CH2CHBrCH3 + H2O Reaction 5.3

2-Bromobutane is a liquid with a boiling point of 91 °C and does not mix with water.

(i) A student plans to prepare 10.0 g of 2-bromobutane using Reaction 5.3.

The percentage yield is 67.0%.

Calculate the mass of CH3CH2CHOHCH3 needed for this preparation.

Give your answer to 3 significant figures.

mass = ...................................................... g [3]

(ii) The student mixes butan-2-ol, sodium bromide and sulfuric acid in a pear-shaped flask, and refluxes the
mixture.

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After 1 hour, the mixture in the flask has separated into two layers: an aqueous layer and an organic layer.

Describe the procedures the student would need to carry out to obtain a pure, dry sample of 2-bromobutane
from this mixture.

[3]

70(a) This question is about titanium (atomic number 22) and its compounds.

Titanium exists as a mixture of five isotopes.

A chemist analyses a sample of titanium using mass spectrometry.

The results are shown in the table below.

Isotope Abundance (%)

46
Ti 8.30
47
Ti 7.40
48
Ti 73.70
49
Ti 5.40
50
Ti 5.20

(i) Calculate the relative atomic mass of titanium in the sample.

Give your answer to 2 decimal places.

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relative atomic mass = ......................................................... [2]

(ii) Complete the electron configuration of a titanium atom.

1s2 [1]

(iii) Complete the table to show the number of protons, neutrons and electrons in a 48Ti2+ ion.

Protons Neutrons Electrons

48
Ti2+ ion
[1]
(b) An ore of titanium contains impure TiO2.

Titanium is manufactured from TiO2 in a two-stage process.

Stage 1 TiO2 + 2C + 2Cl2 → TiCl4 + 2CO Reaction 1.1

Stage 2 TiCl4 + 4Na → Ti + 4NaCl Reaction 1.2

(i) The common name for TiO2 is titanium dioxide.

What is the systematic name of TiO2?

[1]

(ii) In Reaction 1.2, the percentage yield of titanium from TiCl4 is 72.0%.

Calculate the minimum mass, in kg, of sodium that is needed to produce 1.00 kg of titanium.

Give your answer to 3 significant figures.

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mass of sodium = ..................................................... kg [4]

(iii) Reaction 1.2 produces a mixture of titanium and sodium chloride.

Suggest how titanium could be separated from this mixture at room temperature.

Explain your answer.

[2]

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71(a) This question is about some elements in Period 3 and compounds they form.

A student adds a small piece of calcium to a beaker containing an excess of water.

(i) Construct the equation for the reaction and predict one observation that the student would make.

Equation

Observation

[2]

(ii) Suggest one difference that the student would observe in the reaction of barium with water compared to the
reaction of calcium with water.

[1]

(b) A student has a 5.00 g mixture of sodium chloride, NaCl(s), and barium nitrate, Ba(NO3)2(s).

The student also has a solution of sodium sulfate, Na2SO4(aq).

The student uses the method below to determine the percentage by mass of NaCl(s) in the mixture.

Step 1 Dissolve the 5.00g mixture in distilled water.

Step 2 Add an excess of Na2SO4(aq) to the solution. A precipitate of barium sulfate forms.

Step 3 Filter off the precipitate, wash with water, and dry.

Step 4 Weigh the dried precipitate.

The molar mass of barium sulfate is 233.4 g mol–1.

(i) Write an equation for the formation of barium sulfate in step 2.

Include state symbols.

[2]

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(ii) The student obtains 3.28 g of precipitate.

Calculate the percentage by mass of NaCl(s) in the 5.00 g mixture.

Give your answer to 3 significant figures.

percentage by mass of NaCl (s) = ...................................................... % [4]

(iii) The student changes the method in 2(b).

In step 2, the student adds an excess of silver nitrate solution, AgNO3(aq), instead of Na2SO4(aq).

Explain whether this change would allow the student to determine the percentage by mass of NaCl(s) in the
mixture.

[2]

(c) The table below shows melting points and electrical conductivities of some elements in Period 3 and compounds
they form.

Substance Magnesium sulfide, Aluminium, Al Silicon, Si Phosphorus

MgS trichloride, PCl 3

Melting point /
2000 660 1414 –94
°C

Type of lattice
Giant ................... ................... ...................
structure
................... ................... ................... ...................

(i) Complete the table above to show the type of lattice structure of each substance.
[4]

(ii) Explain the following:

• MgS has a higher melting point than PCl 3.

• Al has a greater electrical conductivity than Si.

Melting points

Conductivities

[4]

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72(a) This question is about halogens and halogen compounds.

Chlorine reacts with calcium hydroxide to form Ca(OCl)2, which is the active ingredient in bleaching powder.

2Cl2 + 2Ca(OH)2 → CaCl2 + Ca(OCl)2 + 2H2O

This is a disproportionation reaction.

State what is meant by disproportionation and use oxidation numbers to show that disproportionation has taken
place.

[3]

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(b) A student is studying the hydrolysis of haloalkanes.

The equation for the alkaline hydrolysis of 2-bromopropane, CH3CHBrCH3, is shown below.

CH3CHBrCH3 + OH– → CH3 CHOHCH3 + Br–

Use the curly arrow model to outline the mechanism for the alkaline hydrolysis of 2-bromopropane.

Show relevant dipoles and lone pairs, and name the mechanism.

name of mechanism .......................................................... [3]

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(c) The student sets up an experiment to compare the rates of hydrolysis of 2-bromopropane and 2-iodopropane.

The student uses the method below.

Step 1 Place two test tubes, both containing aqueous silver nitrate and ethanol, in a water bath at 60 °C.

Step 2 Add five drops of 2-bromopropane to one test tube and five drops of 2-iodopropane to the other test
tube.

Step 3 Record the time taken for a precipitate to appear in each test tube.

(i) Complete the table below to show the formula and colour of each precipitate formed.

Haloalkane Formula of precipitate Colour of precipitate

2-bromopropane
2-iodopropane
[2]

(ii) Predict which precipitate would form first and explain the difference in the rates of hydrolysis of
2-bromopropane and 2-iodopropane.

[1]

73(a) This question is about the enthalpy change of combustion of alcohols.

Explain the term enthalpy change of combustion.

[2]

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(b) The enthalpy change of combustion of ethanol, ΔcH, in the gaseous state can be calculated using average bond
enthalpies.

(i) Use this value of ΔcH and the average bond enthalpies below to calculate the average bond enthalpy of
C=O.

Bond Average bond enthalpy / kJ mol–1

C–H +413
C–C +347
C–O +358
O–H +464
O=O +498

C=O bond enthalpy = .............................................kJ mol–1 [4]

(ii) Methoxymethane, CH3OCH3, is an isomer of ethanol.

On combustion, methoxymethane, in the gaseous state, produces carbon dioxide and steam.

ΔcH for methoxymethane is more negative than ΔcH for ethanol.

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Explain why the ΔcH values are different, in terms of the bonds broken and the bonds formed.

[2]

74(a) This question is about alkenes.

A mixture of alkenes is produced when water is eliminated from alcohol A.

(i) What is the systematic name of alcohol A?

[1]

(ii) Alcohol A is refluxed with an acid catalyst.

• A mixture of alkene isomers B, C and D is formed.

• Alkenes B and C show E/Z isomerism but alkene D does not.

Construct the equation for the formation of alkene D from alcohol A.

Show the structure of the organic product.

[2]

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(iii) The skeletal formulae of alkenes B and C are shown below.

Alkene B Alkene C

Skeletal formula

Isomer Z E

Use the Cahn-Ingold-Prelog priority rules to explain why alkene B is the Z isomer.

[2]

(b) A chemistry company is developing water-soluble polymers.

The chemists decide to use compound E, shown below, as the monomer.

(i) Draw a section of the polymer formed, showing two repeat units, and suggest why this polymer is likely to be
soluble in water.

Section of polymer (two repeat units)

[2]

(ii) Outline two ways that waste hydrocarbon polymers can be processed usefully, rather than being disposed of
in landfill sites.

[2]

END OF QUESTION PAPER

APPENDIX

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