Week_7_organic

Week 7 organic (47 marks)
1. Alcohols can be used to prepare organic compounds with different functional groups.
HOOC(CH2)2COOH and HO(CH2)4OH react together to form polymer E.
i. Draw one repeat unit of polymer E.
The functional groups should be clearly displayed.
[2]
ii. Governments are encouraging the development of biodegradable polymers to reduce dependency on
persistent plastic waste derived from fossil fuels.
Polymer E is a biodegradable polymer.

Suggest why polymer E is able to biodegrade.
[1]
iii. A large yield of polymer E can be obtained by reacting a diacyl dichloride with HO(CH2)4OH.
The diacyl dichloride is prepared from HOOC(CH2)2COOH.
Complete the equation for the formation of a diacyl dichloride from HOOC(CH2)2COOH.
[3]
2. The carbonyl compounds, F and G, shown below, contribute to the flavour of coffee.
Compound F reacts with HCN using NaCN(aq) and H+(aq).
i. Outline the mechanism for the reaction of F with NaCN(aq) and H+(aq) and state the name of the
mechanism. The structure of F has been provided.
Include relevant dipoles, lone pairs and the structure of the organic product.
© OCR 2024. You may photocopy this
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Name of mechanism:
[5]
ii. Explain why the mechanism in (i) involves heterolytic fission.
[2]
3. This question is about organic compounds containing nitrogen.
Aspartame, shown below, is an artificial sweetener commonly used as a sugar substitute.
aspartame
i. Aspartame contains several functional groups.
Apart from the benzene ring, name the functional groups in aspartame.

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[3]
ii. A sample of aspartame is hydrolysed with aqueous acid.
Draw the structures of the three organic products of the complete acid hydrolysis of aspartame.
[4]
iii. Some people are concerned that aspartame, C14H18N2O5, may have adverse health effects.
Research shows that the safe maximum daily intake of aspartame is 1.7 × 10−4 mol kg−1.
• A typical UK adult has a mass of 75 kg.

• A can of a diet drink contains 167 mg of aspartame.
How many cans of this diet drink is it safe for a typical adult to drink in one day?
Number of cans = .......................................................... [3]
4. The repeat unit of a polymer is shown below.
Which monomers could form this polymer?

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A
Your answer [1]
5. Compound H is used in the synthesis of polymer I, as shown in the flowchart below.
Complete the flowchart by drawing the structure of the acyl chloride and two repeat units of polymer I, and stating
the formula of the reagent(s) required for the first stage on the dotted line.
[4]

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6. α-Amino acids can react to form proteins.
A short section of a protein chain is shown below.
A student hydrolyses the protein with hot NaOH(aq).
Draw the structures of the organic products formed from this section of the protein.
[3]
7. Which of the following could react with the compound below to form a carbon–carbon bond?
1 CH3Cl and Al Cl3

2 KCN in ethanol
3 CH3OH and H2SO4

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A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer [1]
8. Benzene reacts with an organic reagent in the presence of a halogen carrier to form phenylethanone.
Which organic reagent is required?
A CH3CH2OH
B CH3CHO
C CH3COCl
D CH3COOH
Your answer [1]
9(a). The repeat unit of Nylon 6,6 is shown below.
i. Draw the structures of two monomers that can be used to form Nylon 6,6.
[2]

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ii. A sample of Nylon 6,6 has a relative molecular mass of 21500.
Estimate the number of repeat units in the sample.
Give your answer as a whole number.
number of repeat units = ......................................... [1]
(b). This question is about organic compounds containing nitrogen.
Sodium cyanide, NaCN, can be reacted with many organic compounds to increase the length of a carbon chain.
i. 1-Chloropropane, CH3CH2CH2Cl, reacts with ethanolic sodium cyanide by nucleophilic substitution.
Outline the mechanism for this reaction.
Include curly arrows, relevant dipoles and the structure of the organic product.
[3]

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ii. Compound G is used to synthesise compounds H and I as shown in the flowchart below.
Complete the flowchart showing the structure of compound G and the formulae of the reagents for
Reaction 2 and Reaction 3.
[3]
iii. Compound H reacts with dilute hydrochloric acid to form a salt.
Explain why compound H can react with dilute hydrochloric acid and suggest a structure for the salt
formed.

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Explanation
Structure
[2]
iv. Compound I is the monomer for the biodegradable polymer J.

Draw two repeat units of polymer J and suggest a reason why it is biodegradable.
[3]
END OF QUESTION PAPER

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Mark scheme
Question Answer/Indicative content Marks Guidance

ALLOW the ‘O’ or C=O at either end,
e.g.
2
1 i (AO1.2)
Ester link (must be displayed) ✓ (AO2.5) IGNORE brackets
IGNORE n
Rest of structure ✓ End bonds’ MUST be shown (solid or
dotted)
DO NOT ALLOW more than one

repeat unit
the ester/ ester bond/ ester group
IGNORE references to
/polyester can be broken down ✓
photodegradable
1
ii
OR (AO3.2)
‘Bond breaks’ is not sufficient – no
reference to ester bond
It can be hydrolysed ✓
3
SOCl2 in equation ✓ (AO1.1) ALLOW alternative approach using
iii
(AO1.2) PCl5 or PCl3
Structure of diacyl dichloride ✓ (AO2.6)
Complete balanced equation ✓
Total 6
Mechanism 3
mark ANNOTATE ANSWER WITH TICKS
s AND CROSSES
5
Curly arrow must come from lone pair
(AO1.2)
on C of –CN OR CN–
(AO1.2)
OR from minus sign on C of –CN ion
2 i (AO2.5)
(then lone pair on CN– does not need
(AO2.5)
to be shown)
(AO2.5)
(AO1.1)
Curly arrow from C=O bond must start
Curly arrow from –CN to C atom from, OR be traced back to, any part
of C=O ✓ of C=O bond and go to O
Dipole shown on C=O bond, Cδ+

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and Oδ−,
AND curly arrow from C=O
bond to O atom ✓
Curly arrow from lone pair OR –

charge on O– of correct
intermediate to H+ ✓
----------------------------------
----------------------------------
ALLOW curly arrow to H atom of H2O,
i.e.
Product 1
mark
IGNORE attempt to draw curly arrow

showing breaking of H–O in H2O
---------------------------------- IGNORE lack of dipole on H2O
Name of mechanism 1
mark
Nucleophilic addition
✓
ii Heterolytic 2 ALLOW 2 electrons go to one
One (bonded) atom/O receives both/2 (AO1.2) (bonded) atom/O
electrons ✓ DO NOT ALLOW both pairs of
electrons go to O
Fission
Breaking of a covalent bond ✓ IGNORE formation of ions/radicals
For O atom,
ALLOW species
DO NOT ALLOW element or
molecule
ALLOW π bond in C=O breaks
IGNORE breaking of C=O bond (no

reference to only one bond breaking)
‘Bond breaking’ is not sufficient

(no reference to covalent)
Examiner’s Comments
Candidates often referred to NaCN

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and HCN in their responses.
Candidates who identified the correct
bond breaking often then incorrectly
wrote that the oxygen atom gained the
lone pair of electrons.
Total 7
IGNORE amino acid
ALLOW carboxyl
IGNORE attempt to classify amide,

Ester e.g. secondary
Amide IGNORE formulae (question asks for
Amine names)
3
3 i Carboxylic acid
(AO1.2×3)
4 groups correct ✓ ✓ ✓ IF > 4 functional groups are shown,
3 groups correct ✓ ✓
2 groups correct ✓  Count 4 groups max but
incorrect groups first
IGNORE aryl OR alkyl group

e.g. benzene, phenyl, aryl, arene,
methyl
Methanol 1 mark ALLOW any combination of skeletal

OR structural OR displayed formula
H3C — OH ✓ as long as unambiguous
ALLOW + charge on H of NH3 group,

i.e.NH3+
4
ii
✓ (AO2.5×4) If BOTH amino acids are shown with
NH3 groups (without the + charge) OR
as NH2+ groups, award 2 of the 3
marks for the amino acids
✓ If BOTH amino acids are shown as

correctly balanced salts, e.g NH3Cl, all
Both amino acids shown with NH3+ ✓ marks can be awarded.
iii FIRST CHECK ANSWER ON THE 3 If there is an alternative answer,
ANSWER LINE (AO2.2×3) apply ECF and look for alternative
If answer = 22.4 OR 22 OR 23 award methods
3 marks
Alternative methods
n(aspartame) in 1 can = 0.167 / 294 = n(aspartame) in 1 can = 0.167 / 294
5.68 x 10-4 (mol) ✓ = 5.68 x 10-4 (mol) ✓
n(aspartame) per kg = 5.68 x 10-4 / 75
n(aspartame) limit per day = 1.7x10-4 x = 7.57 x 10-6 (mol) ✓
75 = 0.01275 (mol) ✓
number of cans = 1.7 x 10-4 / 7.57 x
-
number of cans = 0.01275 / 5.68 x 10 10-6

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= 22.4✓
OR
n(aspartame) limit per day = 1.7x10-4 x

75
=0.01275 (mol) ✓
4
= 22.4 ✓
mass(aspartame) limit per day
=0.01275 x 294
= 3.7485 (g) ✓
number of cans = 3.7485 / 0.167

= 22.4 ✓
Total 10
4 A 1 (AO 2.5)
Total 1
5 One mark for each correct 4 ALLOW any combination of skeletal
structure/reagent as shown below OR structural OR displayed formula
as long as unambiguous
ALLOW PCl5 OR PCl3 for reagent

mark.
IGNORE references to temperature
for reagent mark
IGNORE additional reagents shown
with SOCl2/PCl5/PCl3 e.g. H2O, AlCl3,
HCl etc.
IGNORE names (question asks for

structures of organic compounds and
formula of reagent)
DO NOT ALLOW more than two

repeat units
ALLOW 1 mark for one correct repeat
unit
e.g.
‘End bonds’ MUST be shown (do not

have to be dotted)
ALLOW the ‘O’ at either end

i.e.
IGNO
RE brackets
IGNORE n
page.
Compound H was also the focus for
this question. Most candidates were
able to provide the structure of the
acyl chloride obtained from H but only
some identified SOCl2 as the correct
reagent. Common incorrect reagents
included HCl and AlCl3. Most
candidates recognised that polymer I
was a polyester but only some were
able to draw two repeat units
correctly. Candidates are advised to
practice drawing different polymers,
taking care to ensure the correct
number of repeat units are present
when a specific number is required.
Total 4
6 3 ALLOW any combination of skeletal
IGNORE NH3 (question asks for

organic products)
ALLOW –COO– OR –COONa
DO NOT ALLOW negative charge on

C atom
DO NOT ALLOW –COO–Na
(covalent bond) BUT
ALLOW ECF if seen in subsequent
structures
DO NOT ALLOW COOH in this

structure
DO NOT ALLOW (sodium) salt of
alcohol group i.e.
ALLOW COOH groups in this

structure
i.e. award 2 marks for

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IGNORE small slip in carbon chain
i.e. one mark for each group
hydrolysed
This question required candidates to

apply their knowledge of amide
hydrolysis to a section of protein.
Many candidates correctly recognised
that two amino acids would be
produced but not all took account of
the alkaline conditions and showed
COOH groups rather than
carboxylates. Candidates found this
question difficult and although many
gained some credit only the highest
ability candidates, who recognised the
amide in the side-chain would also
react, scored full marks after.
Exemplar 3 shows a good response.
Exemplar 3
This response has correctly identified

the amino acid on the left hand side of
the amide link and also shown this as
a carboxylate. Consequently the first
mark has been achieved. The right
hand amino acid has also been
identified correctly. However, the
amide in the R group has not been
hydrolysed so this response only
scores one of the two marks available
for this product. Notice the candidate
has presented their structures clearly
with the atoms drawn in a similar

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arrangement to the protein shown in
the question. This is a good strategy
to avoid errors and omissions when
drawing organic structures.
Total 3
Candidates found this question

difficult, presumably as it involved
7 B 1 reactions of different functional groups
within the same compound. Many
candidates identified B as the correct
response. The most common incorrect
responses were C and D.
Total 1
8 C 1 Almost all candidates identified C

(CH3COCl) as the reagent required for
this reaction.
Total 1
ALLOW any combination of skeletal
ALLOW
9 a i 2
Examiner Comments
All but the weakest candidates scored
two marks for the two monomers that
could be used to produce Nylon 6,6.
ii 1 MUST be a whole number.
DO NOT ALLOW an answer that uses
an incorrect molar mass in the
working.
ALLOW 96
Examiner Comments
This was a fairly simple calculation
where candidates were expected to
divide the relative molecular mass of
the polymer by the relative molecular
mass of a single repeat unit (226) to
establish the number of repeat units
present in the polymer. Many
candidates obtained the correct
answer. Those that did not gain credit
made a simple error in their

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calculation of the relative molecular
mass of the repeat unit.
Answer 95
ANNOTATE ANSWER WITH TICKS
AND CROSSES
Curly arrow must come from lone pair

on C of −CN OR CN−
OR from minus sign on C of −CN ion
(then lone pair on CN− does not need
to be shown)
IGNORE NaCl
ALLOW SN1 mechanism:
Dipole shown on C–Cl bond, Cδ+ and

Clδ-,
curly arrow from −CN to carbon atom AND curly arrow from C–Cl bond to Cl
of C−Cl bond ✓ atom ✓
Dipole shown on C–Cl bond, Cδ+ and Correct carbocation AND curly arrow
Cl δ−, from
−
AND curly arrow from C−Cl bond to CN to carbocation. Curly arrow must
Cl atom ✓ come from lone pair on C of −CN OR
CN−
OR from minus sign on C of −CN ion
b i 2
(then lone pair on CN− does not need
to be shown) ✓
correct organic product AND Cl− ✓
correct organic product AND Cl-✓
Examiner Comments
The mechanism for the reaction of 1-
chloropropane was well done with the
majority of candidates scoring two or
three of the marks. Marks were not
awarded when candidates used a
negative charge or a lone pair sited on
the nitrogen as the starting point for a
curly arrow in the first stage of the
reaction mechanism. The final
marking point was awarded for the
production of a Cl− ion. The placing of
curly arrows, dipoles and lone pairs of
electrons are important when
communicating by mechanisms.
ii Compound G 3 ALLOW any combination of skeletal
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IGNORE name(s)
ALLOW
ALLOW any suitable metal catalyst

e.g. Pt
ALLOW LiAlH4 for reagent in reaction
2
DO NOT ALLOW NaBH4 for reagent
in reaction 2
IGNORE names (question asks for
formulae)
Reagents IGNORE references to temperature
Reaction 2: H2 AND Ni ✓ and/or pressure
ALLOW H+(aq)
IGNORE dilute
ALLOW formula of an acid AND water
e.g. HCl AND H2O

H2SO4 AND H2O
Reaction Correct formula of an
3: aqueous acid Examiner Comments
e.g. HCl(aq)/H2SO4(aq) ✓ Although many candidates were able
to provide the structure of methanal as
the starting material for this synthesis,
the structures of chloromethanol,
bromomethanol and iodomethanol
were accepted as suitable
alternatives. It should be noted that
hydrolysis is carried out using
aqueous acid and that dilute acid is
not a suitable alternative.
iii Explanation 2 IGNORE NH2 group donates electron
pair
Nitrogen electron pair OR nitrogen
lone pair ALLOW nitrogen donates an electron
AND pair to H+
accepts a proton / H+✓ DO NOT ALLOW nitrogen donates
lone pair to acid
IGNORE comments about the O in the
Structure of salt –OH group
Compound H is a base is not

sufficient (role of lone pair required)
DO NOT ALLOW nitrogen/N lone pair

accepts hydrogen (proton/H+ required)

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ALLOW any combination of skeletal
ALLOW
IF charges are shown both need to be

present
ALLOW charge either on N atom or
NH3+
IF displayed then + charge must be on

the nitrogen
Examiner Comments
Only 20% of candidates were
awarded both marks for this question.
The commonest error was a failure to
state that the N atom has a lone pair
of electrons that can gain a proton.
Answers stating that amines accept
protons or that a salt is produced
when an acid reacts with a base were
not credited. Where a full displayed
structure is given the positive charge
must be shown on the nitrogen atom,
although −NH3+ is acceptable. As the
question required the formula of the
salt, the Cl− had to be included.
iv 3 ALLOW any combination of skeletal
DO NOT ALLOW more than two

Ester link ✓ repeat units for second marking point.
Rest of structure✓ ‘End bonds’ MUST be shown (do not

have to be dotted)
(polymer J is biodegradable because)
the ester / ester bond / ester group / IGNORE brackets
polyester can be hydrolysed✓
IGNORE n
Broken down by water is not sufficient
IGNORE references to
photodegradable
Examiner Comments
The most common mark for this
question was two out of the three
marks available, with candidates

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giving a correct structure of the
polymer but failing to express that the
polymer was biodegradable due the
ability of the ester functional group to
undergo hydrolysis.
Total 14

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Week 7 organic (47 marks)

HOOC(CH2)2COOH and HO(CH2)4OH react together to form polymer E.

i. Draw one repeat unit of polymer E.

The functional groups should be clearly displayed.

Polymer E is a biodegradable polymer.

The diacyl dichloride is prepared from HOOC(CH2)2COOH.

Compound F reacts with HCN using NaCN(aq) and H+(aq).

ii. Explain why the mechanism in (i) involves heterolytic fission.

3. This question is about organic compounds containing nitrogen.

Aspartame, shown below, is an artificial sweetener commonly used as a sugar substitute.

i. Aspartame contains several functional groups.

© OCR 2024. You may photocopy this

ii. A sample of aspartame is hydrolysed with aqueous acid.

• A typical UK adult has a mass of 75 kg.

Number of cans = .......................................................... [3]

4. The repeat unit of a polymer is shown below.

Which monomers could form this polymer?

© OCR 2024. You may photocopy this

Your answer [1]

5. Compound H is used in the synthesis of polymer I, as shown in the flowchart below.

© OCR 2024. You may photocopy this

A short section of a protein chain is shown below.

A student hydrolyses the protein with hot NaOH(aq).

1 CH3Cl and Al Cl3

© OCR 2024. You may photocopy this

Your answer [1]

Which organic reagent is required?

Your answer [1]

9(a). The repeat unit of Nylon 6,6 is shown below.

© OCR 2024. You may photocopy this

number of repeat units = ......................................... [1]

(b). This question is about organic compounds containing nitrogen.

i. 1-Chloropropane, CH3CH2CH2Cl, reacts with ethanolic sodium cyanide by nucleophilic substitution.

Outline the mechanism for this reaction.

© OCR 2024. You may photocopy this

iii. Compound H reacts with dilute hydrochloric acid to form a salt.

© OCR 2024. You may photocopy this

iv. Compound I is the monomer for the biodegradable polymer J.

END OF QUESTION PAPER

© OCR 2024. You may photocopy this

Question Answer/Indicative content Marks Guidance

DO NOT ALLOW more than one

Complete balanced equation ✓

Dipole shown on C=O bond, Cδ+

© OCR 2024. You may photocopy this

Curly arrow from lone pair OR –

IGNORE attempt to draw curly arrow

---------------------------------- IGNORE lack of dipole on H2O

IGNORE breaking of C=O bond (no

‘Bond breaking’ is not sufficient

Candidates often referred to NaCN

© OCR 2024. You may photocopy this

IGNORE attempt to classify amide,

IGNORE aryl OR alkyl group

Methanol 1 mark ALLOW any combination of skeletal

ALLOW + charge on H of NH3 group,

✓ If BOTH amino acids are shown as

© OCR 2024. You may photocopy this

n(aspartame) limit per day = 1.7x10-4 x

number of cans = 3.7485 / 0.167