Q1.

When hexadecane (C16H34) is heated to a high temperature, one molecule of hexadecane

decomposes to form an alkane containing eight carbon atoms and two different
unsaturated compounds.

Which equation could represent this reaction?

A C16H34 → C8H16 + C5H12 + C3H6

B C16H34 → C8H18 + C6H10 + C2H6

C C16H34 → C8H18 + 2 C2H4 + C4H8

D C16H34 → C8H18 + C6H14 + C2H2

(Total 1 mark)

Q2.
2-Bromopropane reacts with bromine to form 2,2-dibromopropane.

What is the name of the mechanism of this reaction?

A Electrophilic addition

B Elimination

C Free-radical substitution

D Nucleophilic substitution
(Total 1 mark)

Q3.
A sample of pure Mg(NO3)2 was decomposed by heating as shown in the equation below.

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

(a) A 3.74 × 10−2 g sample of Mg(NO3)2 was completely decomposed by heating.

Calculate the total volume, in cm3, of gas produced at 60.0 °C and 100 kPa.
Give your answer to the appropriate number of significant figures.
The gas constant R = 8.31 J K−1 mol−1.

Total volume of gas = ___________ cm3

(5)

Page 1 of 19
 (b) The mass of MgO obtained in this experiment is slightly less than that expected
from the mass of Mg(NO3)2 used.
Suggest one practical reason for this.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 6 marks)

Q4.
A student does an investigation to determine the relative formula mass, Mr, of a solid
unknown diprotic acid, H2A

H2A + 2 NaOH → Na2A + 2 H2O

• 250 cm3 of aqueous solution are prepared using 1300 mg of H2A

• A pipette is used to add 25.0 cm3 of 0.112 mol dm–3 aqueous sodium hydroxide to a
conical flask.
• This aqueous sodium hydroxide is titrated with the acid solution.

The titration results are shown in the table.

Rough 1 2 3

Final volume / cm3 27.35 26.75 38.90 35.70

Initial volume / cm3 0.00 0.35 12.15 9.20

Titre / cm3 27.35 26.40 26.75 26.50

(a) Use the results to calculate the Mr of H2A

Mr of H2A _______________________
(5)

Page 2 of 19
 (b) The uncertainty in using the pipette in this experiment is ±0.06 cm3

Calculate the percentage uncertainty in using the pipette.

% uncertainty _________________________
(1)

(c) Before adding the solution from the burette in the rough titration, there was an air
bubble below the tap.
At the end of this titration the air bubble was not there.

Explain why this air bubble increases the final burette reading of the rough titration.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(d) During the titration the student washed the inside of the conical flask with some
distilled water.

Suggest why this washing does not give an incorrect result.

___________________________________________________________________

___________________________________________________________________
(1)
(Total 8 marks)

Q5.
CFCs were used as refrigerants and in aerosols.

The scientists Rowland and Molina published research in 1974 to show that CFCs are
responsible for the destruction of ozone molecules in the upper atmosphere.

A few years later, other scientists discovered that the concentration of ozone in the upper
atmosphere was decreasing.

In 1987 there was an agreement by many countries to restrict the use of CFCs.

Page 3 of 19
(a) The molecule CFC-11 was commonly used as a refrigerant.

Use IUPAC rules to name CFC-11

___________________________________________________________________
(1)

(b) A molecule of CFC-11 breaks down in the upper atmosphere to form a chlorine free
radical.

Give the equation for this reaction.

___________________________________________________________________
(1)

(c) A typical refrigerator contained 0.50 kg of CFC-11 (Mr = 137.5).

One molecule of CFC-11 causes the destruction of approximately 100 000

molecules of ozone.

Use these data to estimate the number of molecules of ozone that can be destroyed
by 0.50 kg of CFC-11
Give your answer in standard form.

The Avogadro constant, L = 6.022 × 1023 mol–1

Number of molecules of ozone ____________________

(2)

(d) State the benefit to life on Earth of ozone in the upper atmosphere.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

Page 4 of 19
 (1)

(e) Suggest one reason why the use of CFCs was not restricted until several years after
Rowland and Molina published their research.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 6 marks)

Q6.
Haloalkanes are used as refrigerants, solvents and anaesthetics.

(a) Trichloromethane (CHCl3) is a haloalkane that can be formed by heating a mixture

of chloromethane (CH3Cl) and chlorine.

(i) Write an overall equation for the formation of trichloromethane by the reaction
of chloromethane with chlorine.

______________________________________________________________
(1)

(ii) Name the mechanism for this formation of trichloromethane.

______________________________________________________________
(1)

(iii) Dichloromethane (CH2Cl2) is an intermediate in this formation of

trichloromethane.

Write an equation for each of the following steps in the mechanism for the
reaction of dichloromethane with chlorine.

Initiation step

______________________________________________________________

First propagation step

______________________________________________________________

Second propagation step

______________________________________________________________

A termination step leading to the formation of a compound with formula

C2H2Cl4

______________________________________________________________
(4)

Page 5 of 19
 (b) Chlorotrifluoromethane (CClF3) is used as a refrigerant, but is being phased out due
to concerns about ozone depletion in the upper atmosphere.
In the upper atmosphere, CClF3 decomposes in the presence of UV light forming a
reactive intermediate that catalyses the decomposition of ozone.

(i) Write an equation to show how CClF3 decomposes to form the reactive
intermediate.

______________________________________________________________
(1)

(ii) Write two equations to show how this reactive intermediate is involved in
catalysing the decomposition of ozone.

1. ____________________________________________________________

2. ____________________________________________________________
(2)
(Total 9 marks)

Q7.
This question is about isomers.

Hex-2-ene has the molecular formula C6H12

(a) Draw the displayed formula of a position isomer of hex-2-ene that exists as E and Z
isomers.

(1)

Page 6 of 19
(b) Draw the displayed formula of a chain isomer of hex-2-ene that does not exist as E
and Z isomers.

(1)

Butanal has the molecular formula C4H8O

(c) Draw the skeletal formula of a functional group isomer of butanal that has an
absorption in the range 1680–1750 cm–1 in its infrared spectrum.

(1)

(d) Draw the skeletal formula of a structural isomer of butanal that has an absorption in
the range 3230–3550 cm–1 in its infrared spectrum.

(1)

(e) Several saturated halogenoalkanes contain 17.8% carbon, 3.0% hydrogen and
79.2% bromine by mass.

Calculate the empirical formula of these compounds.

Page 7 of 19
 Give the IUPAC names of two saturated halogenoalkanes that have this empirical
formula.

Empirical formula ______________________________

Names of halogenoalkanes

1 _________________________________________________________________

2 _________________________________________________________________
(4)
(Total 8 marks)

Q8.
This question is about 2-methylbut-1-ene.

(a) Name the mechanism for the reaction of 2-methylbut-1-ene with concentrated
sulfuric acid.

Outline the mechanism for this reaction to form the major product.

Name of mechanism _________________________________________________

Outline of mechanism to form major product

(5)

Page 8 of 19
(b) Draw the structure of the minor product formed in the reaction in part (a)

Explain why this is the minor product.

Structure of minor product

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Draw the skeletal formula of a functional group isomer of 2-methylbut-1-ene.

(1)

(d) 2-methylbut-1-ene can form a polymer.

State the type of polymerisation.

Draw the repeating unit for the polymer formed.

Type of polymerisation _______________________________________________

Repeating unit

(2)
(Total 11 marks)

Page 9 of 19
Q9.
Alkenes react with bromine (Br2)

(a) Name and outline the mechanism for the reaction of cyclohexene with Br2

Name of mechanism __________________________________________________

Outline of mechanism

(5)

(b) Explain why there is an attraction between a C=C double bond and Br2

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Draw the skeletal formula of the halogenoalkane formed when buta-1,3-diene
(CH2=CHCH=CH2) reacts with an excess of Br2

(1)
(Total 9 marks)

Page 10 of 19
Mark schemes

Q1.
C
C16H34 → C8H18 + 2C2H4 + C4H8
[1]

Q2.
C
Free-radical substitution
[1]

Q3.
(a) Stage 1

Mr for Mg(NO3)2 = 148.3

Moles of Mg(NO3)2 = = 2.522 × 10-4 mol

Extended response calculation
1

Stage 2

Total moles of gas produced = 5/2 × moles of Mg(NO3)2

= 5/2 × 2.522 × 10–4 = 6.305 × 10–4

If ratio in stage 2 is incorrect, maximum marks for stage 3 is
2
1

Stage 3

PV = nRT so volume of gas V = nRT / P

1

V = = 1.745 × 10–5 m3
1

V = 1.745 × 10–5 × 1 × 106 = 17.45 cm3 = 17.5 (cm3)

Answer must be to 3 significant figures (answer could be
17.4 cm3 dependent on intermediate values)
1

(b) Some of the solid is lost in weighing product / solid is blown away with the gas
1
[6]

Page 11 of 19
Q4.
(a) Average titre = 26.45 cm3
M1 = average of concordant titres
1

n(NaOH) = (25 × 0.112 / 1000) = 2.80 × 10–3 mol

M2 – this value only
1

n(acid in titre) = 2.80 × 10–3 / 2 = 1.40 × 10–3 mol

M3 = M2/2
1

n(acid in 250 cm3) = 1.40 × 10–3 × 250/26.45 = 0.0132 mol

M4 = M3 × 250/M1
1

Mr = mass / moles = 1.300/0.0132 = 98.2-98.5

M5 = (1.300/M4) = answer
Mr must be given to at least 1dp
1
Alternatives:
98.6 – scores 4
92.9 – scores 4
87.8 – scores 3
49.3 – scores 3
49.1 – scores 4

(b) % uncertainty = 0.06/25.0 × 100 = 0.24 %

1

(c) Some solution/acid replaces air bubble /

Solution/acid fills below the tap /
Air bubble takes up volume that would be filled by solution/acid
Score for the idea that:
Acid/solution replaces air/bubble/fills jet space
Allow acid/solution fills the bubble/gap
‘The final reading is higher than the volume added’ is not enough.
1

(d) Does not react (with the alkali) / does not change the number of moles (of
alkali)
Allow water is a product / water is not a reagent
1
[8]

Q5.
(a) trichlorofluoromethane
1

(b)

Page 12 of 19
 CCl3F → •CCl2F + •Cl
radical dot anywhere on each radical
1

(c) M1 amount of CFC-11 = ( = 3.64) mol

Allow ECF from M1 to M2
1

M2 molecules of O3 = 3.64 x 100,000 x 6.022 x 1023 = 2.19 x 1029

Allow answers in range 2 x 1029 to 2.20 x 1029 (1sf is
acceptable as this is an estimate)
1

(d) Absorbs (harmful) ultraviolet / uv (light / radiation)

Protects us from (harmful) uv
Ignore other wavelengths / types of light
1

(e) One of these reasons:

• lack of evidence that ozone was being depleted

• lack of alternatives to CFCs
• commercial interest to continue to use CFCs
• hard to obtain international agreement
1

(f) M1 absorbs infrared radiation

M1 idea of IR being taken in
1

M2 molecule has polar bonds

M2 accept polar molecule
1
[8]

Q6.
(a) (i) CH3Cl + 2Cl2 → CHCl3 + 2HCl
IGNORE state symbols
ALLOW multiples
1
(ii) (Free-)radical substitution
This answer only
1
(iii) Initiation:
Cl2 → 2Cl•
Penalise absence of dot once only
1

Page 13 of 19
 1st Propagation step
Cl• + CH2Cl2 → •CHCl2 + HCl
Penalise + and/or – charges every time
1

2nd Propagation step

•CHCl2 + Cl2 → CHCl3 + Cl•
ALLOW • anywhere on •CHCl2 but, if drawn out as a
structure, then
• must be on C
1

Termination
2 •CHCl2 → C2H2Cl4
Mark independently
ALLOW •CH2Cl + •CCl3 → C2H2Cl4
IGNORE state symbols throughout
1

(b) (i) CClF3 → •CF3 +Cl•

ALLOW • anywhere on •CF3 unless displayed
1
(ii) Cl• + O3 → ClO• + O2
Equations can be in either order
Penalise absence of • once only
1

ClO• + O3 → 2O2 + Cl•

ALLOW • anywhere on •ClO
NOT •O3
1
[9]

Q7.
(a)

Displayed structure of hex-3-ene (E or Z isomer)

Award 1 mark if correct molecules given in (a) and (b) but
they are not displayed structures
1

(b)

Page 14 of 19
 Displayed formula of 2-methylpent-2-ene or 3,4-dimethylbut-
2-ene
Allow molecules that are both chain and position isomers, eg
2-methylpent-1-ene, 3-methylpent-1-ene, 4-methylpent-1-
ene, 3,3-dimethylbut-1-ene, 2,3-dimethylbut-1-ene, 2-
ethylbut-1-ene
Award 1 mark if correct compounds given in part (a) and (b)
but they are not displayed formulas
1

(c)

Skeletal formula
Award 1 mark if correct compounds given in part (c) and (d)
but they are not skeletal formulas
1

(d)

Skeletal formula
Alternative answers:

Award 1 mark if correct compounds given in part (c) and (d)

but they are not skeletal formulas
1

Page 15 of 19
 (e) M1 divide %s by relative atomic masses:

Allow ECF from M1 to M2 for a correct empirical formula for

their working in M1
1

M2 (1.48 : 3.00 : 0.99 = 3 : 6 : 2) empirical formula = C3H6Br2

Allow ECF from M2 to M3/4 for compounds that are
saturated halogenoalkanes
1

M3,4 any 2 of:

1,1-dibromopropane
1,2-dibromopropane
1,3-dibromopropane
2,2-dibromopropane
2
[8]

Q8.
(a) Electrophilic addition

NB Allow fully displayed or other structural formulae

if H2O used as electrophile − max 4 ONLY

M2 must show an arrow from = of C=C towards the H atom of the H−O
bond or HO that is part of H−O−S−… on a compound with molecular
formula H2SO4

M2 could have arrow to H+ in which case M3 would be for an

independent H−O bond break on a compound with formula H2SO4

M3: must use an arrow to show the breaking of the H−O bond
M3 ignore partial charges unless wrong

M4: is for the correct carbocation structure

NOT M4 if primary carbocation shown.

M5: must show an arrow from a lone pair of electrons on the correct
oxygen of the negatively charged ion towards the positively charged

Page 16 of 19
 carbon atom
M5 NOT HSO4
credit as shown or as: OSO3H − in which case negative
charge can be shown anywhere ECF from H2SO3 in M2

NB: The arrows are double-headed

IGNORE subsequent use of water to hydrolyse
hydrogensulfate
M1M2M3M4M5

(b)

If tertiary shown here allow as ECF for M1 if primary shown

in (a)
M1

(major) product formed via more stable carbocation OR tertiary

carbocation more stable (than primary)
Must be clear refers to intermediate and not product
M2

Due to electron-releasing character / (positive) inductive effect of three

alkyl groups (as opposed to one)
Primary has one e− donating alkyl group
M3

(c) Skeletal formula of cycloalkane

ignore structure of 2-methylbut-1-ene

1

(d) Addition (polymerisation)

Not additional
Penalise incorrect attachment of ethyl group

Page 17 of 19
 Must have trailing bonds
Ignore n and brackets
Ignore structure of 2-methylbut-1-ene
M1M2
[11]

Q9.
(a) M1 electrophilic addition

All arrows are double-headed. Penalise one mark from the

total for M2-5 if half headed arrows are used.
Do not penalise the “correct” use of “sticks”
Penalise only once in any part of the mechanism for a line
and two dots to show a bond
1

M2 must show an arrow from the double bond towards a Br atom in a Br–Br
molecule
M2 ignore partial negative charges on the double bond
1

M3 must show the breaking of the Br–Br bond

M3 penalise incorrect partial charges on the Br–Br bond and
penalise formal charges
Penalise M4 if there is a bond drawn to the positive charge
1

M4 is for the structure of the correct carbocation

1

M5 must show an arrow from the lone pair of electrons on the Br– towards
the positively charged atom of their carbocation
Max 3 of 4 marks (M2-5) for wrong organic reactant or
wrong carbocation (ignore structure of product)
For M5, credit attack on a partially positively charged
carbocation structure, but penalise M4 for the structure of the
carbocation
1

(b) M1 C=C electron rich / area of high electron density

M1 ignore idea that C=C is negative or highly electronegative
1

M2 Br-Br becomes polarised

1

M3 δ+ Br attracted to C=C
1

Page 18 of 19
(c)

Must be skeletal structure

1
[9]

Page 19 of 19