1. Under suitable conditions, butane, C4H10, reacts with chlorine by radical substitution.

A mixture of organic compounds is formed,

including C4H9Cl , and compounds D and E.
i. Complete the table below to show the mechanism for the initiation and propagation stages of the reaction of C4H10 with chlorine to
form C4H9Cl .

In your equations, use molecular formulae and ‘dots‘ (·) with any radicals.
 
 
 

Equation  
Initiation
 

Conditions  

Propagation   →  

  →  

 
[3]
i. Organic compound D is formed by substitution of all the H atoms in butane by Cl atoms.

Write the equation for the formation of compound D from butane.

Use molecular formulae.

[1]

2. Which compound is unsaturated, alicyclic and contains an alkyl group?

 

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 C

Your answer [1]

3. A section of a polymer is shown below.

Which monomer could form this polymer?

 
A CH3CH(OH)CN
B HOCH2CH2CN
C H2C=CHCN
D NCCH=CHCN

Your answer [1]

  (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]
i. 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.
 
1  
 

2  
 
[2]
 

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5. Electrons occupy orbitals which are arranged in energy levels.

In the diagram below, each box represents an orbital and each electron is shown as an arrow.

Label the sub-shells and add arrows to show how electrons occupy orbitals in an atom of oxygen.

 
[2]
 

6(a). This question is about saturated hydrocarbons.

Compounds A, B and C are saturated hydrocarbons.

The structures and boiling points of A, B and C are shown below.
 

 
• Use the structures to explain what is meant by the term structural isomer.
• Explain the trend in boiling points shown by A, B and C in the table.

[5]

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  (b). Compounds A, B and C all react with chlorine in the presence of ultraviolet radiation to form organic compounds with the formula
C5H11Cl.
i. Name the mechanism for this reaction.

[1]
i. Complete the table to show the number of structural isomers of C5H11Cl that could be formed from the reaction of chlorine with A
and B.
 
 
  A B
   
Number of
structural isomers
........................ ........................
[2]
i. The reaction of compound A with excess chlorine forms a compound D, which has a molar mass of 175.5 g mol . −1

Draw a possible structure for compound D and write the equation for its formation from compound A. Use molecular formulae in the
equation.
 

 
Equation   [2]
 

7. How many structural isomers of C6H14O are tertiary alcohols?

 
A 1
B 2
C 3
D 4

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Your answer [1]

8. The structure of naphthalene is shown below.

What is the molecular formula of naphthalene?

 
A C10H8
B C10H10
C C12H10
D C12H12

Your answer [1]

9. Phosgene, COCl2, exists as simple molecules.

The displayed formula of a phosgene molecule is shown below.

 

i. Draw a ‘dot-and-cross’ diagram of a phosgene molecule.

Show outer electrons only.

[1]
i. Name the shape of a phosgene molecule and explain why it has this shape.
 
Name of shape  
 
Explanation  
 
   
   
  [3]
 

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Mark scheme
 

Question Answer/Indicative content Marks Guidance

Dots NOT required for initiation

IGNORE temperature OR pressure

Dots required in each propagation equation

ALLOW 1 mark for BOTH propagation

equations with any dots missing or extra dots
3
Initiation
(AO1.1) e.g.  C4H10 + Cl → C4H9 + HCl
       C4H9• + Cl2• → C4H9Cl + Cl
Cl2 → 2Cl· AND UV ✓

DO NOT ALLOW charges

1 i Propagation
C4H10 + Cl· → C4H9· + HCl ✓
Examiner’s Comments
(AO2.5)
C4H9· + Cl2 → C4H9Cl + Cl· ✓
A minority of Many candidates scored all 3
(AO2.5) marks for this part, showing that most had
thoroughly learnt the mechanism for radical
substitution. The equation and conditions for
the initiation step were well-known but the
equations for the propagation steps often
included errors. It was common for dots to be
omitted for some radicals and C4H9Cl·, rather
than C4H9·, was often shown for one of the
products in the first propagation stage. H· was
then shown as the other product.

ALLOW structural formulae, e.g.

CH3CH2CH2CH3 + 10Cl2
 
→ CCl3CCl2CCl2CCl3 + 10HCl

ii C4H10 + 10 Cl2 → C4Cl10 + 10 HCl ✓ 1 (AO2.6) Examiner’s Comments

Only the highest attaining candidates were

able to write the correct equation. Although
most candidates did identify the organic
product as C4Cl10, the other product was
usually seen as 5H2 rather than 10HCl.

iii

Total 7

2 C 1 (AO1.2) Examiner’s Comments

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 Unsaturated, alicyclic and alkyl are all terms
that are introduced in AS Chemistry and about
two-thirds of candidates recognised that option
C met the three criteria. From the annotations
on scripts, most candidates ruled out the
saturated option B. A sizeable number of
candidates selected either the aromatic option
A, or structure D which does not possess an
alkyl group. It is important that candidates
learn the terms introduced in the specification
Section 4.1.1, Basic concepts in organic
chemistry.

Total 1

Examiner’s Comments

This part discriminated well. Although most

candidates did select C as the correct
structure, many were diverted into selecting
3 C 1 (AO1.2) option D, the other alternative containing a
double C=C bond. In identifying a monomer
for an addition polymer, candidates are
advised to identify the repeat unit and then to
replace the single C–C bond with a double
bond to give the monomer.

Total 1

4 a i

ii

b i 1(AO2.5) ALLOW correct structural OR displayed

OR skeletal formula

Must show two repeat units

Polymer must have side links

NOTE: C4H9– is allowed for CH3CH2CH2CH2–

IGNORE brackets and use of ‘n’

ALLOW alternating side chains, i.e.

Examiner’s Comments

Over half of the candidates answered this

question incorrectly. Many drew the wrong
repeat units or did not show two repeat units.

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 The structural diagrams were very hard to
decipher and not well drawn.

Exemplar 6

Although the connectivity is not exact, this was

allowed. Many students drew full displayed
structures which were very difficult to decipher
as they often encroached over the writing in
the question.

For energy production,

ALLOW generate electricity/heating

ALLOW as an (organic) feedstock

Examiner’s Comments
Combustion for energy production ✓
Most students did not gain many marks on
ii 2(AO1.1×2)
for production of plastics this question, with a significant number stating
OR other useful organic compounds ✓ that the plastics could be used to feed
livestock or as fertilisers. Those that
mentioned combustion, merely stated plastics
could be used as a fuel. Some candidates
made references to making them
biodegradable or recycling, but these answers
were not given.

Total 11

Sub-shells labels 2
   2s (single box) AND 2p (3 boxes) ✓ (AO1.1) ALLOW single headed arrows, e.g. 1

5 Electrons as arrows Examiner’s Comments

  unpaired electrons in 3 boxes: ↑↓ ↑ ↑
    AND Most candidates added arrows correctly to the
  Paired electrons in single box: ↑↓  ✓ (AO1.2) boxes but the sub-shell labels were sometimes
omitted. Lower attaining candidates
sometimes paired electrons, rather than
showing them singly or showed six electrons
in the 2p sub-shell. This suggested either a
lack of understanding or failure to read the
question.

Total 2

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   For ‘structural’:
Structural isomers: 1 mark   ALLOW different structure
    OR different displayed/ skeletal formula
  Different structural formulae
  AND same molecular formula ✓ DO NOT ALLOW any reference to
spatial/space/3D

Same formula is not sufficient (no ‘molecular’)

Different arrangement of atoms is not

sufficient
  (no ‘structure’/‘structural’)
Common molecular formula: 1 mark
ALLOW 5 carbons and 12 hydrogens
 
  C5H12 for all 3 hydrocarbons ✓ ALLOW for 2 marks:
  Different structural formulae
  AND same molecular formula ✓ of C5H12
  ✓

Comparisons needed throughout

ORA throughout

ALLOW comparison between any alcohols,

e.g.
  A is least branched and has highest b pt
6 a 5   C is most branched and has lowest b pt

ALLOW induced dipole(−dipole) interactions

Boiling point and branching:
IGNORE van der Waals’/vdw forces
 
ALLOW SA for surface area
  1 mark

ALLOW ‘harder to overcome intermolecular

Boiling point decreases with
forces
 
ALLOW more energy to separate the
  more branching
molecules
 
  OR more methyl/alkyl groups/side chains IGNORE just ‘bonds’
  OR shorter carbon chain ✓ intermolecular/London forces required

  Examiner’s Comments
Branching and London forces: 1 mark
This question discriminated well and resulted
Could be seen anywhere within response in a full range of marks. Most candidates were
More branching gives less (surface) contact aware that structural isomers have different
  structural formulae but the same molecular
  AND formulae. It was common though for
  fewer/weaker London forces ✓ candidates to refer to different arrangements
of atoms in space, clearly confusing with
stereoisomerism. The best candidates used
  the structures (as in the question) to show that
Energy and intermolecular forces: 1 mark the common molecular formula was C5H12.

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 Candidates were expected to link the amount
of surface contact between molecules with
induced dipole–dipole forces or London
forces. ‘Contact’ or the name of the
intermolecular forces was often omitted.
Finally, candidates were expected to link the
  amount of branching to the strength of the
Less energy to break London forces/ intermolecular forces and the energy needed
  intermolecular forces/intermolecular to change state. Lower ability candidates often
bonds/ ✓ let themselves down by being unable to
construct a well-reasoned response. There
was often a gulf between the clear responses
of able candidates and those of lower ability
candidates.

ALLOW Free radical substitution

b i Radical substitution ✓ 1 Examiner’s Comments

Most candidates identified this reaction as

radical substitution.

Examiner’s Comments
 
ii A B 2 Most candidates achieved at least one mark,
3✓ 2✓ particularly for isomer A. Successful
candidates often drew structures of the
isomers alongside the table to help with their
response.

iii 2

Structure of D
  ALLOW correct structural OR displayed
Structure of a trichloro isomer of A, OR skeletal formula OR mixture of the above
 
e.g. (as long as unambiguous)

 
IGNORE molecular formula
✓
  ALLOW any trichloro isomer of A
  CHECK carefully

Equation ALLOW multiples,

  e.g. 2C5H12 + 6Cl2 → 2C5H9Cl3 + 6HCl
  C5H12 + 3Cl2 → C5H9Cl3 + 3HCl ✓
  Molecular formulae required
Examiner’s Comments

NO ECF from incorrect structure of D Many candidates correctly drew the structure

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 of compound D but comparatively few were
able to construct a correct equation. For this
equation, candidates needed to apply their
knowledge and understanding of
monosubstitution of alkanes to substitution of
three H atoms by three Cl atoms. This task
proved to be one of the most difficult questions
on this paper. The exemplar shows an
excellent response. The candidate has drawn
a trisubstituted structure that fits the molar
mass of 175.5 g mol−1 and a correct equation
for its formation. Many attempts at this
equation showed H2 as the second product
rather than HCl.

Exemplar 6

Total 10

ALLOW 3

Examiner’s Comments

7 C 1
The responses showed a reasonably even
split across all options with relatively few
correct responses of C. A good route to
success here is to draw out the possibilities.

Total 1

Examiner’s Comments

Many candidates added H atoms to the

8 A 1 structure to aid their choice. Most candidates
selected the correct response of A, with a
sizeable number selecting B (by adding two H
atoms where the two rings join).

Total 1

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 NOTE: O and Cl electrons MUST be shown
differently from C electrons (e.g. expected
answer)

IGNORE inner shells

ALLOW diagram with missing C, O or Cl

symbols.

For C=O bond, ALLOW sequence × × • •

9 i 1 ALLOW non-bonding electrons unpaired

CARE: Check that lone pairs on Cl and O are
included
 Cl (×2) has 6 non-bonded electrons
Examiner’s Comments
(3 LPs)
 O has 4 non-bonded electrons (2
Most candidates attempted a dot-and-cross
LPs)
diagram of a COCl2 molecule, with ionic
representations being rare. Candidates should
take care to include any lone pairs in their
diagrams. Omission of the O and Cl lone pairs
was the most common error.

ALLOW bp for bonded pair

Shape
 
  Trigonal planar ✓ ALLOW 3 bonded pairs (BOD)
 
  OR 3 sigma bonds
Number of bonded regions OR 2 bonded pairs and 1 double
 
(C has)    3 electron (dense) regions bond
  OR 4 bonded pairs including a
 
double bond
  OR 3 bonding regions ✓
IGNORE bonded atoms

IGNORE just 3 bonds

ii 3 ALLOW alternative phrases/words for repel

e.g. ‘push apart’

IGNORE electrons repel (pairs needed)

Electron pair repulsion (Seen anywhere)

DO NOT ALLOW atoms repel
 
electron pairs/bonded pairs/bonded
  Examiner’s Comments
regions repel
This question discriminated well. Most
  OR
candidates recognised that a COCl2 molecule
electron pairs move as far apart as
  has a trigonal planar shape. The best answers
possible
  OR explained this shape in terms of the three
  bonds repel ✓ electron regions around the central C atom
and their repulsion.

Total 4

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