Yr12 Mid topic assessment 4a Name ………………………………………………………..

Target Grade …………… Mark ……………./41 Grade ………………

1. What is the best description for the bonding between the carbon atoms in an ethene molecule?

A One σ-bond and one π-bond

B One π-bond
C Two σ-bonds
D Two π-bonds

Your answer [1]

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

Your answer [1]

3. Which statement about an electrophile is correct?

A It is an electron pair acceptor.

B It is a proton donor.
C It is a negative ion.
D It is a species with an unpaired electron.

Your answer [1]

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4. 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]

5(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]

ii. Complete the table to show the number of structural isomers of C 5H11Cl that could be formed from the reaction of
chlorine with A and B.

A B

Number of
structural isomers
........................ ........................
[2]
iii. 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]

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

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 State the reagents and conditions for reaction 1.

[1]

(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]

(c). Compound C forms an addition polymer E.

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]

7(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). 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.

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.

vi. Further substitution forms a mixture of organic products.

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

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8. Compound B, shown below, can be used to synthesise organic compounds with different functional groups.

i. Compound B is a member of a homologous series.

Name the homologous series and state its general formula.

Homologous series
.................................................................................................................................
General formula
..................................................................................................................................
ii. What reagents and conditions are needed to convert compound B into a saturated hydrocarbon?

[1]

9. The displayed formula for a hydrocarbon is shown below.

How many σ and π bonds are present in a molecule of this hydrocarbon?

σ bonds π bonds
A 2 4
B 10 2
C 10 4
D 12 2

Your answer
[1]

10. Which compound has non-polar molecules?

A E‐1,2‐dichlorobut‐2‐ene

Z‐2,3‐dichlorobut‐2‐ene
B E‐2,3‐dichlorobut‐2‐ene
C

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 D Z-1,4‐dichlorobut‐2‐ene

Your answer
[1]

11. The organic compounds labelled A to E below are all produced by living organisms.

Compound D reacts readily with hydrogen chloride in an addition reaction. Two products are
formed in this reaction, but one of the products is formed in much greater amounts than the other.

i. Draw the structure of both possible addition products of this reaction.

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 [2]

ii. State and explain which of the two possible products will be formed in greater amounts.
Include a diagram of the intermediate in the mechanism of this reaction in your answer.

[2]

iii. 4.125 g of compound D is reacted with an excess of hydrogen chloride. The mixture of products contains 95% by
mass of one product and 5% by mass of the other product.

Calculate the mass of each product formed.

[2]

END OF QUESTION PAPER

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Mark scheme

Question Answer/Indicative content Marks Guidance

Examiner’s Comments

Candidates answered this question well with

over two-thirds choosing the correct option A.
1 A 1 (AO1.1)
Option D was the most common incorrect
response suggesting that candidates are
uncertain about the nature of a C=C double
bond.

Total 1

Examiner’s Comments

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
2 C 1 (AO1.2)
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

3 A 1 (AO1.1)

Total 1

Examiner’s Comments

This part discriminated well. Although most

candidates did select C as the correct
structure, many were diverted into selecting
4 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

For ‘structural’:
5 a 5
Structural isomers: 1 mark ALLOW different structure

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 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
Common molecular formula: 1 mark (no ‘structure’/‘structural’)

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
C is most branched and has lowest b pt
Boiling point and branching:
ALLOW induced dipole(−dipole) interactions
1 mark IGNORE van der Waals’/vdw forces
ALLOW SA for surface area

Boiling point decreases with

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

Branching and London forces: 1 mark

Examiner’s Comments

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

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 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
Less energy to break London forces/ branching to the strength of the
intermolecular forces/intermolecular intermolecular forces and the energy needed
bonds/ ✓
to change state. Lower ability candidates
often 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, e.g. OR skeletal formula OR mixture of the above
(as long as unambiguous)

✓ IGNORE molecular formula

ALLOW any trichloro isomer of A
CHECK carefully

Equation
ALLOW multiples,
C5H12 + 3Cl2 → C5H9Cl3 + 3HCl ✓ e.g. 2C5H12 + 6Cl2 → 2C5H9Cl3 + 6HCl
Molecular formulae required

Examiner’s Comments

NO ECF from incorrect structure of D

Many candidates correctly drew the structure
of compound D but comparatively few were

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 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

Examiner’s Comments
steam
6 a AND 1 Many candidates knew the answer to this
Acid/H+ (catalyst) ✓ question but forgot that water must be in the
gaseous state. There were numerous
responses stating nickel as the catalyst, but
most knew that an acid catalyst was required.

Examiner’s Comments

b i 1,2-dibromo-1,1-dichloroethane✓ 1
This question was generally well answered,
although some candidates made careless
mistakes such as not writing -di or writing 1,2-
dibromo-1-dichloroethane

ANNOTATE ANSWER WITH TICKS AND

CROSSES ETC
For curly arrows, ALLOW straight or
snake-like arrows and small gaps (see
ii 3 examples):
1st curly arrow must

1st curly arrow (from ANY alkene) • go to a Br atom of Br–Br

Curly arrow from double bond to Br • AND

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 start from, OR be traced back to any point
•
across width of C=C

of Br–Br ✓
2nd curly arrow must
DO NOT ALLOW partial charge on
C=C
 start from, OR be traced back to, any
part of δ+Br−δ− bond
2nd curly arrow
 AND go to δ−
Correct dipole on Br Br
AND curly arrow for breaking of
Br–Br bond ✓

3rd curly arrow

Correct carbocation with + charge on
C with 3 bonds 3rd curly arrow must
AND curly arrow from Br− to C+
• go to the C+ of carbocation
of carbocation ✓
• AND
DO NOT ALLOW δ+ on C
start from, OR be traced back to any point
of carbocation •
across width of lone pair on :Br−
OR start from – charge on Br– ion
•

(Lone pair NOT needed if curly arrow shown

from – charge on Br−)
i.e. ALLOW carbonium + on either
C atom
Examiner’s Comments

DO NOT ALLOW half headed or double headed

Many candidates gained all three marks on
arrows but allow ECF if seen more than once
this question and the diagrams were clear and
easy to read. Lower ability candidates had
incorrect dipoles or curly arrows that could not
be traced back to the correct origin.
Candidates should be encouraged to consider
what the arrows mean rather than memorising
mechanisms with no understanding.

c i 2 For repeat unit,

 displayed formula required

 ‘side bonds’ required on either side
of repeat unit from C atoms
Correct polymer with side links and brackets ✓  ALLOW section containing more
than one repeat unit

Equation balanced with n ✓

DO NOT ALLOW ECF from incorrect repeat
unit

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 n on LHS at any height to the left of the
formula
n on RHS must be subscript

TAKE CARE of ‘n’ position on both sides of Examiner’s Comments

equation.
Most candidates correctly drew the repeat unit
and were credited with one mark, but many
placed the n position in the wrong place on
the left-hand side of the equation or forgot to
write it in at all.

ALLOW reduced use of fossil fuels

ALLOW less landfill / less harm to wildlife

Advantage (1 mark)
Energy production / (energy) used to produce
electricity ✓ ALLOW chlorine/Cl OR Cl2

Disadvantage (1 mark) ALLOW toxic/poisonous waste products

Formation of HCl/products of combustion cause
ii 2
acid rain Examiner’s Comments
OR
Formation of CO2/gases that cause global With all the media interest in plastic pollution
warming / greenhouse gases this question was answered well, although
OR many gave the answer ‘quick and efficient’ as
Formation of CO✓ an advantage which was not credited.
Candidates should beware of vague
statements such as these. Many wrote
‘harmful’ instead of toxic, or ‘bad for the
environment’ instead of being specific about
the environmental issue.

Total 9

CnH2nO2 Examiner’s Comment:

7 a OR 1
CnH2n+1COOH ✔ The correct response; CnH2nO2 or
CnH2n+1COOH, was presented by a good
proportion of candidates but many incorrect
alternatives were seen.

ALLOW sunlight
IGNORE temperature

b i Ultraviolet (radiation)/UV ✔ 1
Examiner’s Comments

Most candidates scored this mark.

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 ALLOW C2H5COOH + Cl2 → C2H4ClCOOH +
HCl
ALLOW C3H6O2 + Cl2 → C3H5ClO2 + HCl

Examiner’s Comments
ii CH3CH2COOH + Cl2 → CH3CHClCOOH + HCl ✔ 1
Many candidates could write the overall
equation but there was some confusion with
propagation steps and some equations
contained radicals or missed out HCl as a
product.

ALLOW the breaking of a covalent bond

where each atom keeps one of the bonding
electrons
IGNORE particle for atom
ALLOW one electron from the bond goes to
each product / species
DO NOT ALLOW molecule or compound for
atom
one electron from the bond (pair) goes to each IGNORE homolytic fission equations
iii 1
atom / chlorine/radical ✔
Examiner’s Comments

Homolytic fission is described in the

specification in terms of each bonding atom
receiving one electron from the bonded pair
forming two radicals. A large proportion of
candidates failed to match the essential points
in this definition.

ALLOW
1. Cl· + C3H6O2 → C3H5O2· + HCl
2. C3H5O2· + Cl2 → C3H5ClO2+ Cl·
ALLOW dot at any position on the radical
ALLOW 1 mark if both equations correct but
Propagation step 1
Cl· + CH3CH2COOH → CH3CHCOOH· + HCl any dots omitted from radicals
iv ✔ 2
Propagation step 2 Examiner’s Comments
CH3CHCOOH· + CI2 → CH3CHCICOOH + Cl·
✔
Generally well answered. Candidates took
note of the instruction in the question and it
was very rare to see radicals without their
unpaired electron.

v 1 Dot shown in correct position

ALLOW –OH

Examiner’s Comments

Unfortunately, candidates who were not able

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 to attempt equations for the propagation
steps in part (iv) were then unable to suggest
the structure of the radical formed in the first
step. Many candidates did not present a fully
displayed formula. However, formulae
showing –OH were given credit in this
question.

ALLOW correct structural OR skeletal OR

displayed formula OR mixture of the above

DO NOT ALLOW C3H4Cl2O2

Any structure with two or more Cl atoms on alkyl
chain
(provided that one Cl is at C–2) ALLOW further substitution into any or all of
the 4 positions occupied by H atoms in the
vi 1
alkyl group, provided that at least one Cl is at
C–2
e.g.
Examiner’s Comment:

Generally well answered but it was clear from

some of the structures drawn that some
candidates did not understand what is meant
by further substitution.

Total 8

IGNORE branched before alkene

Examiner's Comments

8 i Alkene AND CnH2n ✓ 1

This part was answered very well. Most
candidates identified Compound B as a
member of the alkenes and showed the
correct general formula of CnH2n.

ii Hydrogen/H2 AND Ni (catalyst) ✓ 1 ALLOW Pt OR Pd OR Rh

ALLOW hydrogenation for hydrogen

IGNORE any temperature and pressure

stated

Examiner's Comments

A surprisingly large number of candidates

answered this part poorly. Many candidates
identified either hydrogen or nickel, but not
both. Other common errors included steam
and H3PO4. This was an easy question and
the incorrect answers reflected that many
candidates had not learnt organic reagents

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 and conditions for the reactions in the
specification.

Total 2

Examiner's Comments
9 D 1
B was a common incorrect answer with the
sigma bond not counted as part of a double
bond.

Total 1

Examiner's Comments

Candidates struggled with this very different

10 B 1
polarity question. The majority of candidates
are clearly used to applying symmetry to
much simpler molecules.

Total 1

allow any unambiguous structure or formula.

allow ecf on the second structure for

11 i 2
hydrogen atom errors if candidate tries to
convert to a displayed / structural formula, but
(1) (1) the carbon skeleton must be correct.

correct structure of either possible carbocation

intermediate shown (1) If both carbocations are drawn, only one
needs to be correct to score the mark.
the tertiary halogenoalkane (which will be labelled
ii 2
as either product 1 or product 2) is identified as allow ecf from (i) for correct justification of
the one formed in greater amounts … product formed in greater amount based on
because the carbocation more stable on C3 than incorrect structures.
C2 owtte (1)

iii Amount of D that reacts 2

M(D: C7H16O) = 110 (g mol−1)

AND

n(C7H16O) = =
0.0375 (mol) (1)

Masses of two products formed

M(product: C7H17OCl) = 146.5 (g mol−1)

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 AND

AND

allow mass of both products

= 0.0375 × 146.5 = 5.49 g

iii Mass of 5% product = 0.0375 × × 146.5 =

0.27 g (1)
allow ‘product 1’ and ‘product 2’ if linked to
correct mass given labelling in (i) and
reasoning in (ii) (allow ecf from (ii)).

Total 6

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