Answer all the questions.

1. A chemist reacts the following compound with hydrogen bromide, HBr.

What is the name of the major product?

A 2-Bromo-3-methylbutane
B 2-Bromo-2-methylbutane
C 3-Bromo-3-methylbutane
D 3-Bromo-2-methylbutane

Your answer

[1]

2. A section of a polymer chain is shown below.

Identify the monomer that would give rise to this section of addition polymer.

A E-But-2-ene
B Z-But-2-ene
C Methylpropene
D Propene

Your answer
[1]

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3. 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]

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4. Hydrogen bromide reacts with 3-methylbut-1-ene.

What is the structure of the major intermediate formed in the mechanism?

Your answer
[1]
5. How many stereoisomers are there of CH3CH = CHCH(OH)CH2CH = CH2?

A 2
B 4
C 6
D 8

Your answer
[1]

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6. Alkenes can be used to make polymers.

(i) Phenylethene, C6H5CHCH2, undergoes addition polymerisation.

Write a balanced equation for the addition polymerisation of phenylethene.

You should show the structures of the monomer and polymer clearly.

[2]

(ii) Waste polymers are often put into landfill sites.

State one way of processing waste polymers usefully, other than landfill and recycling.

[1]

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7. Cyclobutane is a cycloalkane.

There are several unsaturated isomers of cyclobutane that are alkenes.

Two of these isomers are stereoisomers.

(i) Explain what is meant by the term stereoisomers.

[1]

(ii) Draw these two stereoisomers.

[2]

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8. 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]

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9. Chloroethene, CH2CHCl, can be polymerised to form poly(chloroethene).

Write an equation, using displayed formulae, to show the formation of this polymer.

[2]
10. Butan-2-ol can be prepared using two different methods.

State the catalyst required for Method 1.

[1]

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11. This question is about the compounds shown below.

Polymer H can be disposed of by combustion. One environmental problem is the production of toxic gases, such
as CO.

(i) Draw the structure of the monomer needed to produce polymer H.

[1]

(ii) Give the formula of an acidic toxic gas that could form during combustion of polymer H.

[1]

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12(a). Allyl bromide, CH2=CHCH2Br, is used in the production of polymers.

Part of the C=C double bond in allyl bromide is called a π-bond.

Draw a labelled diagram to show the formation of the π-bond.

[2]
(b). Allyl bromide, CH2=CHCH2Br, reacts with bromine, Br2.

(i) Outline the mechanism of this reaction.

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

[4]

(ii) Name the type of mechanism.

[1]

(c). Allyl bromide is reacted as shown below.

(i) State the reagents and conditions for step 1.

[1]

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 (ii) In step 2, 1-bromopropane reacts with chlorine by radical substitution.

Outline the mechanism for the monochlorination of 1-bromopropane.

In your mechanism, you can show the formula of 1-bromopropane as C3H7Br.

Include the names of the three stages in this mechanism, state the essential conditions and all termination
steps.

[5]

(iii) Radical substitution produces a mixture of organic products.

Suggest two reasons why.

[2]

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13. 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.

[2]

(ii) State and explain which of the two possible products will be formed in greater amounts.

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 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]

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14. 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]

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15. 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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16(a). This question is about alkenes.

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). 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]

(c). 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. Methyl allyl chloride, MAC, is a chemical used in the production of insecticides. The structure of MAC is shown
below.

MAC

The flowchart below shows some reactions of MAC.

(i) Complete the flowchart above.

Draw the structure of the product of Reaction 1.
Draw the structure of the minor organic product of Reaction 2 (Compound B).
[2]

(ii) Reaction 2 creates a mixture of compounds. Compound A is the major product.

Draw the mechanism for the formation of compound A.

Use curly arrows and show relevant dipoles.

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 [3]

(iii) Explain why compound B is the minor product of Reaction 2.

[1]

(iv) MAC reacts with water in the presence of AgNO3(aq) and ethanol.

Draw the structure of the organic product of this reaction.

State what you would observe in this reaction and identify the compound responsible for the observation.

[2]

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18(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.

(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.

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

[2]

(b). *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.

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 [6]

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19. Stearic acid, oleic acid and linoleic acid are examples of naturally occurring fatty acids.

Traditional name Structure Systematic name

Stearic acid C17H35COOH Octadecanoic acid
Oleic acid C17H33COOH Octadec-9-enoic acid
Linoleic acid C17H31COOH Octadeca-9,12-dienoic acid

Partial hydrogenation of linoleic acid may result in the formation of trans-octadec-12-enoic acid.

(i) Draw the skeletal formula of trans-octadec-12-enoic acid.

[2]

(ii) Some fatty acids show cis-trans isomerism because there is restricted rotation about a C=C double bond.

State one other feature of these molecules that enables them to show cis-trans isomerism.

[1]

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20. 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]

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21. Compound A is an unsaturated hydrocarbon that can be used as the starting material for the production of
organic compounds.

The flowchart shows three addition reactions of compound A.

(i) In the boxes below, show the structures of the organic products formed in the reactions.

[4]

(ii) What are the essential conditions for the reaction of compound A with H2O?

[2]

(iii) Using curly arrows, outline the mechanism for the reaction of compound A with Br2.

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 [3]

(iv) Name the mechanism in part (iii).

[1]

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22(a). Hex-2-ene shows E/Z isomerism.

(i) Draw the skeletal formulae of E-hex-2-ene and Z-hex-2-ene.

E-hex-2-ene Z-hex-2-ene

[2]

(ii) State and explain the features of a hex-2-ene molecule that lead to E and Z isomers.

[2]

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(b). A section of a polymer that can be made from an unsaturated hydrocarbon B is shown below.

(i) Add brackets to the section of the polymer to show one repeat unit.

[1]

(ii) Draw the structure of hydrocarbon B.

[1]

(iii) The polymer has a relative molecular mass of 50,000.

Calculate the number of monomer molecules required to make one molecule of the polymer.

number of monomer molecules = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [1]

END OF QUESTION PAPER

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

1 B 1

Total 1

2 D 1

Total 1

3 D 1
Examiner's Comments

B was a common incorrect answer with the

sigma bond not counted as part of a
double bond.

Total 1

4 B 1

Total 1

5 B 1

Total 1

6 i 2 ALLOW any combination of skeletal OR

structural OR displayed formula as long as
unambiguous

Correct polymer with side links

Balanced equation for formation of correct n on LHS can be at any height to the left of
polymer - correct use of n in the equation formula AND n on the RHS must be a
and brackets subscript (essentially below the side link)

ii Use as an organic feedstock 1 ALLOW the production of plastics or

monomers or new polymers
OR

Combustion for energy production Combustion alone is not sufficient

Total 3

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

7 i (Compounds with the) same structural 1 ALLOW different spatial arrangement of

formula but a different arrangement (of atoms.
atoms) in space ✔ DO NOT ALLOW different displayed
formula.

Examiner's Comments

Although many candidates were able to

provide the correct definition, some
responses did not state that stereoisomers
have the same structural formula.

ii 2 ALLOW displayed OR skeletal formula OR

mixture of the above.
ALLOW structures in either order
IGNORE molecular formula
✔ ✔ IGNORE structural formula
IGNORE names
IGNORE E/Z and cis / trans labels
ALLOW 1 mark for a pair of E/Z isomers of
an incorrect
hydrocarbon structure with four C atoms
e.g. C, or CH or CH2 instead of CH3
groups.

Examiner's Comments

This question required candidates to

identify isomers of cyclobutane that would
exhibit stereoisomerism and proved
challenging for some. The more able
candidates were able to provide two
correct structures. A significant number of
candidates suggested cyclic alkenes,
which were not isomers of cyclobutane.

Total 3

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

8 i Curly arrow from double bond to Br of 4 Curly arrow must start from bond and go to
Br–Br (1) correct atom

Correct dipole shown on Br–Br do not allow partial charges on C=C bond
AND curly arrow showing breaking of
Br–Br bond (1)

allow carbocation on terminal CH2

Correct carbocation with + charge on C

with 3 bonds
AND
curly arrow from Br– to C+ of carbocation do not allow δ+ on C of carbocation
(1)
Curly arrow must come from a lone pair on
Br–OR from the negative sign of Br– ion
(then lone pair on Br– ion does not need to
be shown)
Correct product: (1)
allow formation of bromonium intermediate
and curly arrows, i.e.:

ii Movement of a pair of electrons 1 allow movement of a lone pair

Total 5

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

9 2 Displayed formulae MUST be used to

award each mark

Correct polymer with side links ✔

Balanced equation for formation of correct n on LHS can be at any height to the left of
polymer - correct use of n in the equation formula
and brackets ✔ AND n on the RHS must be a subscript
(essentially below the side link)

Examiner's Comments

The majority of candidates were able to

show the displayed formula for the correct
polymer. Surprisingly, many candidates
failed to score the second mark because
they did not consider balancing the
equation on the left-hand side by inserting
an n before the chloroethene monomer.

Total 2

10 Acid ✔ 1 ALLOW H+ / named mineral acid / H2SO4 /

H3PO4

DO NOT ALLOW ‘weak acid’ e.g. ethanoic

acid

IGNORE pressure
IGNORE temperature

Examiner's Comments

This question was answered well and the

majority of candidates identified a suitable
catalyst for the hydration of an alkene. A
common incorrect response was nickel.

Total 1

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

11 i 1 ALLOW correct structural OR displayed

OR skeletal OR mixture of the above

ALLOW E isomer

Examiner's Comments

The monomer of polymer H was correctly

identified by the majority of the cohort.
However, a small proportion of candidates
simply drew the repeat unit of H.

ii HCL ✔ 1 DO NOT ALLOW Cl2

IGNORE names
IGNORE nitrogen oxides / NOx

Examiner's Comments

Most candidate were able to provide the

formula of HCl. Common incorrect answers
included ClO and Cl2.

Total 2

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

12 a 2 Note: A diagram is required for each mark

DO NOT ALLOW C=C in one diagram but

ALLOW ECF for subsequent use in
another diagram.

The bonds shown in the diagram are

required
First mark ALLOW ECF for missing bonds in second
diagram on left with p-orbitals labelled diagram
OR unlabelled diagram AND the IGNORE any atoms joined to the bonds
statement: (sideways)
overlap of p orbitals ✔
ALLOW a diagram where the p-orbitals are
linked for second mark.
Second mark
(labelled) diagram on right showing π-bond
✔
e.g.

Examiner's Comments

Most candidates produced reasonable

diagrams to illustrate the formation of a π-
bond. A common mistake was showing a
C=C group rather a C—C bond in the
centre of each structure. Omission of the
peripheral bonds was also frequently seen.
Although over half of the cohort received
some credit in this part it was clear that
many candidates found this question
difficult. Only the most able scored both
marks.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

b i 4 ANNOTATE ANSWER WITH TICKS AND

CROSSES ETC
Curly arrow from double bond to Br of Curly arrow must start from bond and go
Br–Br ✔ to correct atom

Correct dipole shown on Br–Br DO NOT ALLOW any other partial charges
AND curly arrow showing breaking of e.g. shown on double bond
Br–Br bond ✔

ALLOW carbocation on terminal CH2

Correct carbocation with + charge on C
with 3 bonds
AND
curly arrow from Br– to C+ of carbocation ✔

DO NOT ALLOW δ+ on C of carbocation.

Curly arrow must come from a lone pair on

Br–
OR from the negative sign of Br– ion (then
lone pair on Br– ion does not need to be
Correct product: ✔ shown)

Examiner's Comments

There were many excellent attempts at this

mechanism and it is clearly well
understood by candidates at this level.
Consequently the majority of candidates
scored three or four marks. In some cases
the placement of the curly arrow from the
C=C group was the cause for a candidate
to only score three marks. Curly arrows
should be drawn accurately. Where an
arrow is expected to come from a bond,
candidates are encouraged to start the
arrow touching the bond.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

ii Electrophilic addition ✔ 1
Examiner's Comments

The name of this mechanism was also well

known by most candidates.

c i H2AND Ni (catalyst) ✔ 1 ALLOW name or formula for each

IGNORE any stated temperature and
pressure

Examiner's Comments

To score the mark in this question

candidates had to state that both hydrogen
and nickel were required for step 1. It was
often the case that only one of these was
stated. Although hydrogen was often seen
as a reagent it was common to see an
incorrect catalyst, such as H2SO4.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

ii 5 ANNOTATE ANSWER WITH TICKS AND

CROSSES ETC
(Initiation)
Cl2 → 2Cl AND UV ✔ DO NOT ALLOW any ECF in this question

(Propagation) IGNORE references to temperature

C3H7Br + Cl → C3H6Br + HCl ✔
THROUGHOUT, ALLOW correct
C3H6Br + Cl2 → C3H6BrCl + Cl ✔ molecular formulae OR structural OR
displayed OR skeletal OR mixture of the
above

(Termination) IGNORE dots

Two from the three termination equations IGNORE state symbols
below ✔
2Cl → Cl2
IGNORE one incorrect termination
C3H6Br + Cl → C3H6BrCl equation

2C3H6Br → C6H12Br2 Examiner's Comments

names of steps initiation, propagation and This question required candidates to apply
termination linked to one correct equation their knowledge of the radical substitution
for each step in this mechanism✔ mechanism to form a bromochloroalkane.
Examiners were encouraged by the
number of excellent attempts and it is clear
that candidates had prepared well for this
type of question. Consequently most
candidates scored four or five marks. A
common reason for a candidate only
scoring four marks was the omission of UV
radiation as an essential condition.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

iii 2 IGNORE mixture of organic products (in

question)

further substitution ALLOW dichloro / multichloro / dibromo /

OR multibromo compounds formed
produces different termination products OR an example of a further substitution
OR product
More than one termination step✔ OR an example of a different termination
product
ALLOW more than one hydrogen (atom)
can be replaced
ALLOW radicals react with each other to
form other products
substitution at different positions along
chain ✔ ALLOW forms different structural isomers
ALLOW a hydrogen (atom) on a different
carbon (atom) can be replaced

Examiner's Comments

Candidates often found it difficult to provide

clearly written explanations for this
question. The majorly of responses
focused on further substitution or the idea
of different termination steps. Only the best
candidates recognised that chlorination of
1-bromopropane would produce a mixture
of structural isomers.

Total 15

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

13 i 2 allow any unambiguous structure or

formula.

allow ecf on the second structure for

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

ii correct structure of either possible 2 If both carbocations are drawn, only one
carbocation intermediate shown (1) needs to be correct to score the mark.

the tertiary halogenoalkane (which will be allow ecf from (i) for correct justification of
labelled as either product 1 or product 2) is product formed in greater amount based
identified as the one formed in greater on incorrect structures.
amounts …
because the carbocation more stable on
C3 than 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)

AND

AND

iii allow mass of both products

Mass of 5% product = 0.0375 × × = 0.0375 × 146.5 = 5.49 g
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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 Mark Scheme

Question Answer/Indicative content Marks Guidance

14 Electron pair acceptor (1) 2

I+ (1)

Total 2

15 i (because) molecule contains only single 1 allow no multiple bonds / no double or

C–C bonds (1) triple bonds
allow contains single bonds only

ii 109.5° 1

iii Combustion for energy production 2

(alternative to fossil fuels) (1)
Use as an organic feedstock (1)

Total 4

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

16 a i Overlap of orbitals directly between the 1 allow a correct diagram

bonding atoms

ii 120° AND trigonal planar 1 allow planar triangle

b i One of the carbons of the C=C has two of 1 allow a stereoisomer must have 2 different
the same groups attached / has two groups attached to each carbon of the C=C
hydrogen atoms attached (so it can't show double bond
2 different stereoisomers)

ii 1 mark each correct DIAGRAM 2 allow correct skeletal OR displayed

formula OR mixture

but must clearly show arrangement around

C=C

(1) (1)

c E isomer 1 E with no explanation is insufficient

AND
F takes priority over the carbon on the left
hand side (as it has a higher atomic
number)
AND
CH2OH takes priority over the CH3 group
on the right hand side

Total 6

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

17 i 2 ALLOW correct structural OR displayed

OR skeletal formulae OR a combination of
above as long as unambiguous
From Reaction 1 =

compound B =

ii 3 ALLOW correct structural OR displayed

Curly arrow from C=C to OR skeletal formulae OR a combination of
attack the H atom above as long as unambiguous.
Curly arrow must start from covalent bonds
and not atoms.

Correct dipole on H—Cl

AND curly arrow from bond to DO NOT ALLOW any other partial charges
Cl e.g. shown on double bond.

Correct carbocation /
carbonium ion with full
positive charge shown AND DO NOT ALLOW Cδ+ for charge on
correct curly arrow from carbonium ion.
negative charge of Cl– to Curly arrow from Cl– can start from the
correct carbon atom OR negative charge or the lone pair.
correct curly arrow from lone DO NOT ALLOW delta negative, i.e. Clδ–.
pair of Cl– to correct carbon
atom

iii because the intermediate / carbocation in 1

the formation of compound B is less stable
(than the intermediate in the formation of
compound A)

iv 2 ALLOW correct structural OR displayed

OR skeletal formulae OR a combination of
above as long as unambiguous.

(Formation of) white precipitate / solid /

suspension AND (ppt is) silver chloride /
AgCl

Total 8

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

18 a i Any one from: 1 IGNORE the length of the σ bond and π

bond

σ bond is between bonding

atoms/nuclei AND π bond is above and
below the bonding atoms / nuclei
σ bond has direct/head-on overlap of
orbitals IGNORE the type of orbital for σ bond
AND π bond has sideways overlap
π bond has a lower bond enthalpy / is Examiner's Comments
weaker than a σ bond
σ bond has electron density between The vast majority of candidates were
bonding atoms unable to describe the difference between
AND π bond has electron density a σ and a π bond. The simplest answer
above and below bonding atoms ✔ was that the π bond was the weaker bond
or the σ bond was the stronger. Many
candidates attempted to describe how the
two different bonds were formed. It was
clear that candidates understood the
concept of the sideways overlap of the p
orbitals to form theπ bond but were unable
to describe the formation of the σ bond. A
common misconception was that the σ
bond could only be formed by the
overlapping of the s orbitals. The best
candidates were able to articulate that the
σ bond results from the head on overlap of
orbitals resulting in the bond forming
directly between two atoms whereas the π
bond results in the electron density being
located above and below the plane of the
bonding atoms.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

ii One carbon atom (in double bond) is 1 ALLOW

attached to two groups which are identical /
the same ✓ One carbon atom in (double bond) is
not attached to (two) different
groups/groups of atoms
Right-hand carbon is attached to two
groups that are the same/two methyl
groups.
Two groups are the same on right-
hand side
Three groups are the same (on the
double bond)

DO NOT ALLOW

Two groups on the same side of the

double bond
Must be right-hand side; Same side
could be top or bottom)
Functional groups OR molecules for
groups

Examiner's Comments

This question required candidates to apply

their knowledge of E/Z isomerism to
suggest why compound A did not have E/Z
isomers. Whilst it was clear that many
candidates understood the concept of E/Z
isomerism many found it difficult to apply
this concept and articulate an explanation.

iii 1 Mark Independently

ALLOW correct structural OR displayed

OR skeletal formulae OR a combination of
above as long as unambiguous

ALLOW C2H5 for CH2CH3

IGNORE connectivity of alkyl groups BUT

..............DO NOT ALLOW –CH3CH2

iii (Z-)pent-2-ene ✓ 1 DO NOT ALLOW trans-pent-2-ene

Examiner's Comments

Most candidates were able to draw the

structural isomer of compound A and
provide a suitable name.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

b Please refer to marking instructions on 6 Throughout: ALLOW correct structural OR

page 4 of mark scheme for guidance on displayed OR skeletal formulae OR a
how to mark this question. combination of above if unambiguous

Level 3 (5–6 marks) Indicative scientific points

A comprehensive description with all three
scientific points explained thoroughly. 1. Two possible products of reaction

There is a well-developed and detailed CH3C(CH3)BrCH2CH3

description of the mechanism, including CH3CHBrCH(CH3)CH3
correct structures, accurately drawn curly IGNORE names where correct
arrows and using charges and dipoles structures are present
consistently. Candidates compare tertiary
and secondary carbocation stability to 2. Mechanism for formation of either
justify major product. product.

Level 2 (3–4 marks) Curly arrow from C=C to attack the H atom
Attempts to describe all three scientific of the HBr
points but explanations may be incomplete. Correct dipole on H–Br Curly arrow from
OR Explains two scientific points H–Br bond to Br
thoroughly with no omissions. Carbocation with full positive charge on
The description has some structures with carbon atom Curly arrow from negative
reasonably accurate curly arrows and charge on Br– or lone pair on Br– to carbon
some charges and dipoles identified. atom with positive charge

Level 1 (1–2 marks)

A simple description based on at least two
of the main scientific points
OR Explains one scientific point thoroughly
with few omissions.
or
The description is communicated in an
unstructured way, including some use of
curly arrows, charges or dipoles.

0 marks
No response worthy of credit.

3. Major organic product

Major product: 2-bromo-2-methylbutane

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

Major product is formed from the most
stable carbocation intermediate
OR –Br is attached to carbon atom with
the least hydrogens attached
OR the carbon with the most –CH3
groups attached
OR the –H is attached to the carbon
atom with most hydrogens attached

Examiner's Comments

The first of the six mark level of response

questions required candidates to draw the
mechanism of electrophilic addition, outline
the two possible products and explain
which one of these products would be the
most likely to be formed. The most
common mark for this question was five
marks mainly due to candidates not being
able to explain the formation of the major
product in terms of the formation of the
more stable tertiary carbocation in the
intermediate stage of the mechanism.
Candidate scoring five marks frequently
quoted Markownikoff's rule as an
explanation. Varying degrees of
competence was displayed in the
production of the mechanism. The correct
positioning of curly arrows was a skill that
the most candidates had clearly mastered
with many accurate mechanisms being
submitted. Weaker candidates clearly need
more time to develop these skills.

Total 10

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

19 i M1 1 Must be skeletal formula for M1

Correct structure of a mono unsaturated
fatty acid with 18 C ✓

M2
Correct position of double bond (12) in a DO NOT ALLOW cis isomer for M2
mono unsaturated fatty acid
AND trans arrangement ✓ Examiner's Comments

Well answered by the majority of

candidates. Incorrect chain length and
putting the double bond in the wrong
position were the most common errors.

ii Each carbon atom in the double bond is 1 ALLOW Each carbon atom of the double
attached to (two) different groups/atoms ✓ bond is attached to a H atom
DO NOT ALLOW functional group for
group
DO NOT ALLOW the carbon atoms are
attached to different groups
IGNORE two of the substituent groups are
the same

Examiner's Comments

Many candidates failed to score the mark

for this simple definition with reference to
the carbon atoms in the double bond a
common omission.

Total 3

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

20 i Alkene AND CnH2n ✓ 1 IGNORE branched before alkene

Examiner's Comments

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/H2AND 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 and conditions for
the reactions in the specification.

Total 2

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

21 i 4 ALLOW correct structural OR displayed

OR skeletal formula OR mixture of the
Product from Br2 above

IGNORE names

WATCH for missed methyl stick

ALLOW added H shown,

i.e.
Product from H2/Ni

Mixture of isomers from H2O ALLOW in either order

Examiner's Comments

Most of the candidates were able to show

correct structures for all four organic
products. The majority of these candidates
used skeletal formulae. A small proportion
of responses included incomplete
structures. These included a missing Br
atom on the product from the reaction of
compound A with Br2 or a missing methyl
group. Candidates should be advised to
check structures carefully, especially when
using skeletal formulae.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

ii Steam OR temperature ≥ 100°C ✓ 2 ALLOW H2O(g)

IGNORE pressure
IGNORE High temperature / reflux
acid (catalyst) ✓

ALLOW H+ / named mineral acid / H2SO4 /

H3PO4
DO NOT ALLOW ‘weak acid’ e.g. ethanoic
acid

Examiner's Comments

Most candidates were able to state that an

acid catalyst was required for the reaction
of compound A with H2O. However,
although many candidates recognised the
need for the reaction to be heated only the
strongest responses referred to
temperatures above 100 °C. It was not
uncommon to see vague responses that
simply referred to a high temperature.
Candidates should be encouraged to give
precise conditions for the hydration
reaction of an alkene.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

iii 3 ANNOTATE ANSWER WITH TICKS AND

CROSSES

Curly arrow from double bond to Br of

Br–Br ✓ Curly arrow must start from bond and go
to correct atom
Correct dipole shown on Br–Br
AND curly arrow showing breaking of
Br–Br bond ✓ DO NOT ALLOW any other partial charges
e.g. shown on C=C bond

_____________________________
Correct carbocation with + charge on C
AND
curly arrow from Br– to C+ of carbocation ✓ DO NOT ALLOW δ+ on C of carbocation.

IF C atoms are displayed IGNORE missing

bonds to H atoms

Curly arrow must come from a lone pair on

Br–
OR from the negative sign of Br– ion (then
lone pair on Br– ion does not need to be
shown)
Note: ‘+’ and ‘–’ are fine for charge (circles
used for clarity) Examiner's Comments

The mechanism of the reaction of

compound A with Br2 was well known and
consequently the majority of candidates
scored all three marks. A common reason
for scoring only two marks was inaccurate
placement of the curly arrow from the
bromide ion to the carbocation
intermediate. This arrow should start from
either a lone pair or the minus sign of the
bromide ion.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

iv electrophilic addition ✓ 1
Examiner's Comments

Most of the candidates were able to name

the mechanism correctly. However it was
not uncommon to see incorrect responses
which included electrophilic substitution
and nucleophilic addition.

Total 10

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

22 a i 2
ALLOW 1 mark if skeletal formulae of both
E and Z hex-2-ene are shown but in the
incorrect columns

IF correct unambiguous structural OR

displayed OR mixture of formulae are
shown ALLOW 1 mark if both
stereoisomers are in the correct columns
e.g the following scores 1 mark

IF the skeletal formula of E hex-3-ene is

shown in the first box ALLOW 1 mark for
the skeletal formula of Z hex-3-ene as ECF

Examiner's Comments

It was anticipated that most candidates

would be able to provide the skeletal
formulae for the E and Z isomers of
hex-2-ene but this proved not to be the
case. A large number of responses
displayed the C=C group and gave
structural formulae for the side chains,
while others confused E and Z, placing the
isomers in the incorrect columns. A
number of candidates opted to use an
ambiguous formula and it was not
uncommon to see C3H7 attached to a C=C
group. Candidates should be made aware
of the importance of showing each C atom
when a question requires structural detail.

ii (carbon-carbon) double bond does not 2

rotate OR has restricted rotation ✓ Examiner's Comments

Each carbon atom of the double bond Most candidates recognised that the C=C
attached to (two) different groups / atoms group had restricted rotation which resulted
✓ in E/Z isomerism. However, many
struggled to explain that each C atom in
the C=C group was bonded to different
groups with sufficient clarity.

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 Mark Scheme

Question Answer/Indicative content Marks Guidance

b i 1 ALLOW repeat unit at any point along the

section provided that it works, e.g.

One repeat unit shown ✓

(could be any of the three repeat units Examiner's Comments
shown)
The majority of candidates were able to
use brackets to show the repeat of the
polymer shown. A number of candidates
placed brackets inaccurately, often
intersecting carbon atoms in the backbone.

ii Structure of pent-2-ene: 1 ALLOW correct structural OR displayed

OR skeletal formula OR mixture of the
above (as long as unambiguous)

Examiner's Comments

Candidates found this part more difficult

than part (c)(i). Many candidates correctly
✓
drew the structure of pent-2-ene as
hydrocarbon B but a wide range of other
responses was seen. Two common
incorrect responses were the structures of
either 2-methylpent-2-ene or
2-methylpentane.

iii 1 MUST be a whole number

(50,000/70 =) 714 OR 715 ✓
Examiner's Comments

Many candidates were able to use the

repeat unit identified in (c)(i) or the
monomer in (c)(ii) to determine the number
of monomer molecules in the polymer.

Total 7

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