OCR A-Level Chemistry Synthesis and analytical techniques (02), November 2021: Question 17

10 marks · Medium difficulty · Structured Questions

Explain ozone depletion by Freon-13, draw the repeat unit of an oligomer from 2-chloro-1,1,2-trifluoroethene and explain its boiling point, and draw structures for the monomers 1,4-diaminobutane and benzene-1,4-diacyl dichloride along with one repeat unit of their polyamide polymer.

Practise this question

Question

Question 17 about haloalkanes and polymers. Part (a) asks to explain ozone depletion by Freon-13 (CClF3) with equations using dots for unpaired electrons (3 marks). Part (b)(i) asks to draw the repeat unit of an oligomer made from 2-chloro-1,1,2-trifluoroethene (1 mark), and (b)(ii) asks to explain why increasing the number of repeat units increases boiling point (2 marks). Part (c) provides two boxes to draw the structures of monomers 1,4-diaminobutane and benzene-1,4-diacyl dichloride, and a large bottom box to draw one repeat unit of the resulting polymer (4 marks).
Question text

17 This question is about haloalkanes and polymers.

(a) Freon-13, is a CFC with the molecular formula CClF3.

In the upper atmosphere, the presence of Freon-13 can lead to ozone depletion.

Explain, with the aid of equations, how Freon-13 can lead to this ozone depletion.

Use ‘dots’ (•) to show the position of unpaired electrons.

… [3]

(b) An oligomer is a polymer with a low molecular mass and a small number of repeat units.

An oligomer made from 2-chloro-1,1,2-trifluoroethene is used as a lubricating oil.

(i) Draw the repeat unit of this oligomer.

[1]

(ii) The boiling point of the lubricating oil can be increased by increasing the number of

repeat units.

Explain this statement.

… [2]

(c) A polymer can be made from the monomers:

• 1,4-diaminobutane

• benzene-1,4-diacyl dichloride.

Draw the structures of these monomers and one repeat unit of the polymer.

1,4-diaminobutane benzene-1,4-diacyl dichloride

one repeat unit of polymer

[4]

Mark scheme

Show the mark scheme Mark scheme for question 17 showing required equations for chlorine radical formation and ozone breakdown in part (a), the correct displayed formula for the halogenated oligomer repeat unit in part (b)(i), points regarding surface contact and intermolecular forces for part (b)(ii), and complete chemical structures for the diamine monomer, diacyl dichloride monomer, and the polyamide repeat unit with amide links and open end bonds for part (c).

AO

Question Answer Marks Guidance

element

17 (a) Formation of Cl• 3 IGNORE dots for formation Cl•,

CClF3 → CF3 • + Cl • AO2.5 i.e. ALLOW CClF3 → CF3 + Cl

Breakdown of O3 DO NOT ALLOW ECF

Cl • + O3 → •ClO + O2 AO1.1 Dots required in this equation

×2

•ClO + O → Cl • + O2 IGNORE O + O3 → 2O2

ALLOW 1 mark if both equations are correct by

atom but dot(s) missing or incorrect

(b) (i) 1 AO2.5 ALLOW any combination of skeletal

OR structural OR displayed formula as long as

unambiguous

‘End bonds’ MUST be shown

DO NOT ALLOW more than 1 repeat unit

IGNORE brackets

IGNORE n

(ii) 2 AO2.1 Both answers need to be a comparison

×2

More points of contact / more surface interaction IGNORE surface area

(between molecules) ALLOW more electrons

AND

Stronger/more dipole(–dipole) interactions ALLOW induced/permanent dipole interactions

ALLOW London forces

ALLOW van der Waals’ forces (as permanent

dipole-dipole and induced dipole-dipole

interactions are present within this polymer)

IGNORE IDID

More energy needed to break the intermolecular forces

9 AO

element

(c) 4

AO2.5

×2

For polymer, DO NOT ALLOW > 1 repeat unit

‘End bonds’ MUST be shown

(do not have to be dotted)

AO1.2 ALLOW –NH– at either end

Amide link: i.e.

1 repeat unit of correct polymer: AO2.5

IGNORE brackets

IGNORE n

Total 10

How to answer it

Haloalkanes, Ozone Depletion, and Condensation Polymers

What this question tests

This question evaluates your understanding of radical substitution mechanisms in atmospheric chemistry (CFCs and ozone depletion), intermolecular forces in addition polymers, and structural representations of monomers and condensation polymers (polyamides).

Question 17 (a) - [3 Marks]

Ozone Depletion by Freon-13

✅ Correct Answers

You must give three distinct propagation/formation equations showing radical catalysis:

  1. CCl₃F → CCl₂F• + Cl• (Formation of chlorine radical)
  2. Cl• + O₃ → ClO• + O₂ (Breakdown of ozone)
  3. ClO• + O → Cl• + O₂ (Regeneration of chlorine radical)

💡 Key Knowledge

  • CFCs photolyse in the stratosphere via homolytic fission initiated by UV light.
  • Chlorine radicals ( Cl• ) act as catalysts because they are regenerated in the overall cycle.
  • Unpaired electrons must be shown clearly as a dot ( • ).

🧠 Exam Technique

  • Always double-check that every radical species features a clearly visible dot.
  • Ensure equations balance in terms of atoms and radicals.

❌ Common Errors

  • Omitting the radical dot ( • ), which loses marks instantly.
  • Confusing propagation steps with termination steps.
Mark scheme guidance: Dots are strictly required in all equations. Allow 1 mark if both propagation equations are correct by atom count, but the radical doting is missing or misplaced.
Question 17 (b)(i) - [1 Mark]

Oligomer Repeat Unit

✅ Correct Answers

For the oligomer made from 2-chloro-1,1,2-trifluoroethene ( CFCl=CF₂ ):

Draw the backbone carbon-carbon single bond with extending end bonds passing through brackets or touching the main chain:

-[CFCl-CF₂]- or backbone with F, Cl, F, F attached appropriately.

💡 Key Knowledge

Addition polymerisation converts the carbon-carbon double bond ( C=C ) into a single bond ( C-C ) with open bonds representing continuation.

❌ Common Errors

  • Drawing more than one repeat unit (do not write n unless outside brackets, but better to avoid entirely if unsure).
  • Leaving out the essential end bonds extending past the repeat units.
Mark scheme guidance: 'End bonds' MUST be shown. Brackets and subscript n are ignored. Do NOT allow more than 1 repeat unit.
Question 17 (b)(ii) - [2 Marks]

Boiling Point and Chain Length

✅ Correct Answers

  1. Larger molecules have more surface contact / larger surface area between molecules.
  2. This leads to stronger / more induced dipole-dipole interactions (London forces), requiring more energy to overcome.

💡 Key Knowledge

As polymer chains get longer, temporary instantaneous dipole-induced dipole interactions accumulate along the length of the backbone.

🧠 Exam Technique

This is a standard comparative question. You must make a comparison linking molecule size/contact surface directly to the energy required to break intermolecular forces.

❌ Common Errors

  • Stating that covalent bonds within the polymer chain are broken during boiling (a major conceptual error—intermolecular forces break, not covalent bonds).
Mark scheme guidance: Both comparative points required for full marks (more points of contact/surface interaction AND stronger/more dipole-dipole interactions + energy needed).
Question 17 (c) - [4 Marks]

Monomers and Condensation Polymer Repeat Unit

✅ Correct Answers

  1. 1,4-diaminobutane: H₂N-CH₂-CH₂-CH₂-CH₂-NH₂
  2. Benzene-1,4-diacyl dichloride: Benzene ring attached directly to two opposite -COCl groups.
  3. Repeat unit of polymer: -[HN-CH₂-CH₂-CH₂-CH₂-NH-CO-(benzene ring)-CO]- with clear amide linkages ( -NH-CO- ) and correct end bonds.

💡 Key Knowledge

Condensation polymerisation between a diamine and a diacyl dichloride forms a polyamide with the elimination of hydrogen chloride ( HCl ).

🧠 Exam Technique

Check the linkage carefully: amine nitrogen ( N ) bonds directly to the carbonyl carbon ( C=O ) of the acyl chloride to create the characteristic peptide/amide bond.

❌ Common Errors

  • Drawing ester linkages ( -COO- ) instead of amide linkages ( -CONH- ).
  • Retaining the -Cl or extra H atoms inside the polymer repeat unit structure.
Mark scheme guidance: Amide link must be correct. Exactly 1 repeat unit required with explicit end bonds.

Topics

Module 4: Core organic chemistry · Module 6: Organic chemistry and analysis · 6.2 Nitrogen compounds, polymers and synthesis · 4.2 Alcohols, haloalkanes and analysis

Question and mark scheme from the OCR A-Level Chemistry examination, Synthesis and analytical techniques (02), November 2021. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.