Edexcel A-Level Chemistry Paper 2, June 2017: Question 6
9 marks · Medium difficulty · Short Open Response
Deduce addition and condensation polymers, draw enantiomers of 2-hydroxypropanoic acid, and explain their optical activity and the advantages of biodegradable polyesters.
Practise this questionQuestion
Question text
6 This is a question about polymerisation.
(a) But-1-ene and cyclohexene both form addition polymers.
Draw a section of each polymer, showing two repeat units.
(2)
CH2 CHCH2CH3 r
r
(b) Deduce the two monomers needed to produce the polyamide shown.
(2)
O H
N
N
O H
and
(c) Deduce the single monomer that could be used to produce the polyamide shown.
(1)
O
N
H
*P48059A01024*
(d) PLA is a biodegradable polyester which is made from 2-hydroxypropanoic acid,
CH3CH(OH)COOH.
(i) Draw the two enantiomers of 2-hydroxypropanoic acid.
(2)
(ii) State how separate samples of these two enantiomers could be distinguished
in a laboratory.
(1)
(iii) Biodegradable polyesters break down naturally.
State why this is an advantage.
(1)
(Total for Question 6 = 9 marks)
Mark scheme
Show the mark scheme
Question
Answer Additional Guidance Mark
Number
6(a) Accept skeletal, structural or (2)
displayed formulae or
combination of which is clear,
e.g. −C2H5
( CH2=CHCH2CH3→) (1)
Brackets are not essential
Ignore ‘n’
Ignore orientation of side chains
Ignore bond length
Ignore where bond goes to for
the ethyl groups
Penalise lack of ‘end-bonds’ once
only
Award 1 mark max if only one
repeat unit given for each
( →) (1) polymer
Ignore more than 2 repeat units
Question
Answer Additional Guidance Mark
Number
6(b) HOOC ― (CH2)4 ― COOH Accept skeletal, structural or (2)
or displayed formulae
ClOC ― (CH2)4 ― COCl (1)
Penalise use of C4H8 once only
H2N ― (CH2)4 ― NH2 (1) Penalise missing H’s once only
The monomers can be in either order
Do not award monofunctionality
Question
Answer Additional Guidance Mark
Number
6(c) H2N ― (CH2)4 ― COOH Accept skeletal, structural or (1)
displayed formulae
Allow H2N ― (CH2)4 ― COCl
Ignore connectivity
Allow
Allow use of C4H8 here only
Penalise missing hydrogens
Question
Answer Additional Guidance Mark
Number
6(d)(i) Allow Diagram must be 3-dimensional with (2)
either wedges or dashes to score 2
marks
Ignore orientation of group at the top
Ignore vertical bond to H of OH group
Question
Answer Additional Guidance Mark
Number
6(d)(ii) They rotate the plane of plane-polarised light (equally) Allow one plane (1)
and in opposite/different directions
OR
Determine in which direction they rotate the plane of
plane-polarised light
Question
Answer Additional Guidance Mark
Number
6(d)(iii) Does not accumulate in the environment/does not occupy Accept answers that outline the (1)
landfill benefit of avoiding other means of
disposal such as incineration, use of
toxic chemicals
Ignore just less harm to
environment/less harm to animal
life/less pollution/less of an
“eyesore”/less energy to break it
down
(Total for Question 6 = 9 marks)
How to answer it
Polymerisation, Polyamides & Optical Isomerism Study Guide
What this question tests
This question assesses your understanding of addition and condensation polymerisation, structural analysis of repeat units, stereoisomerism (enantiomers and 3D tetrahedral drawing using wedges and dashes), analytical techniques for optical isomers (plane-polarised light), and the environmental impacts of biodegradable polymers.
Drawing Addition Polymer Repeat Units
Task: Draw a section of the addition polymer for both but-1-ene and cyclohexene, showing two repeat units. (2 marks)
✅ Correct Answer
- But-1-ene polymer: Backbone chain of 4 carbons repeated twice (8 carbons total in the main chain backbone), with ethyl side chains pointing off alternate carbons, enclosed in square brackets with bonds extending outside.
- Cyclohexene polymer: Backbone containing two joined ring units with opening/closing bonds extending through the brackets.
💡 Key Knowledge
- Addition polymers form when unsaturated double bonds (C=C) open up and link together.
- When drawing "two repeat units", the backbone carbon chain must be double the length of a single monomer unit (e.g., 4 carbons in the monomer become an 8-carbon backbone for 2 repeat units).
- End bonds (extension bonds) must cut through the square brackets.
❌ Common Errors & Examiner Pitfalls
- Showing only one repeat unit when the question explicitly requests two (limits the score to a maximum of 1 mark overall).
- Omitting the extension bonds passing through the square brackets, or adding them outside the brackets incorrectly.
- Failing to show the ethyl group properly attached as a side chain for but-1-ene.
🧠 Exam Technique
- Always redraw the monomer with the C=C bond written horizontally as C=C to make conversion to the polymer straightforward.
- Check your carbon count before moving on: 2 carbons per monomer × 2 units = 4 backbone carbons for ethene-derivatives, but here but-1-ene has 4 carbons per monomer, so 2 units require 8 backbone carbons!
Deducing Monomers from a Polyamide Structure
Task: Deduce the two monomers needed to produce the given polyamide structure. (2 marks)
✅ Correct Answer
- Dicarboxylic acid / Diacyl dichloride: HOOC-(CH₂)₄-COOH (or ClOC-(CH₂)₄-COCl )
- Diamine: H₂N-(CH₂)₄-NH₂
💡 Key Knowledge
- Polyamides are formed by condensation polymerisation between a dicarboxylic acid (or diyl chloride) and a diamine, releasing water (or HCl).
- To find the monomers, locate the peptide/amide link ( -CO-NH- ) and hydrolyse (break) the bond down the middle to reveal the functional groups at each end.
❌ Common Errors & Examiner Pitfalls
- Forgetting to include the terminal functional groups ( -COOH and -NH₂ ), leaving dangling carbon chains instead of complete molecules.
- Writing monofunctional species instead of di-functional monomers.
🧠 Exam Technique
- Count the carbon chain length carefully between the functional groups in the repeat unit diagram to avoid miscounting CH₂ groups.
- Monomers can be given in either order; clearly separate them with the word "and" or a comma.
Deducing a Single Monomer for a Polyamide
Task: Deduce the single monomer that could be used to produce the cyclic-derived polyamide shown. (1 mark)
✅ Correct Answer
H₂N-(CH₂)₄-COOH (an amino acid containing both an amine and a carboxylic acid group).
💡 Key Knowledge
- A single monomer can form a polyamide if it possesses both a -NH₂ group and a -COOH group (an amino acid).
- Alternatively, a cyclic lactam structure is also accepted by the mark scheme.
❌ Common Errors & Examiner Pitfalls
Leaving out the hydrogen atoms on the amine group ( -NH₂ ) or writing an incomplete carbon backbone length.
Drawing Enantiomers
Task: Draw the two enantiomers of 2-hydroxypropanoic acid ( CH₃CH(OH)COOH ). (2 marks)
✅ Correct Answer
Two 3D tetrahedral structures drawn around a central chiral carbon atom, shown as non-superimposable mirror images using wedges (bonds coming out) and dashes (bonds going into the page).
🧠 Exam Technique & 3D Drawing Rules
- Mandatory 3D representation: You must use wedge and dashed bonds to indicate spatial arrangement. Simple flat line structures score 0 marks.
- Draw one isomer completely, then draw its direct reflection across an imaginary mirror plane for the second enantiomer.
- The four groups attached to the central C are: -H , -OH , -CH₃ , and -COOH .
Distinguishing Enantiomers in a Laboratory
Task: State how separate samples of these two enantiomers could be distinguished in a laboratory. (1 mark)
✅ Correct Answer
Use a polarimeter to measure how they rotate the plane of plane-polarised light in opposite (equal and opposite) directions.
💡 Key Knowledge
- Enantiomers are optically active.
- One enantiomer rotates plane-polarised light clockwise (+), and the other rotates it counter-clockwise (-).
❌ Common Errors & Examiner Pitfalls
Vague answers like "measure their melting points" or "use spectroscopy" (enantiomers share identical physical and chemical properties in achiral environments, except for their interaction with plane-polarised light and chiral reagents).
Advantages of Biodegradable Polyesters
Task: State why biodegradable polyesters breaking down naturally is an advantage. (1 mark)
✅ Correct Answer
They do not accumulate in the environment / do not occupy landfill space / avoid toxic waste disposal methods like incineration.
💡 Key Knowledge
- Biodegradable polymers can be broken down by microorganisms into small natural molecules (like CO₂ and water).
- This reduces the long-term pollution crisis associated with non-biodegradable addition polymers (like polyalkenes).
❌ Common Errors & Examiner Pitfalls
Too-vague statements such as "it's better for the environment" or "reduces pollution" without specifying landfill reduction or lack of persistence/accumulation.
Topics
Organic Chemistry · Topic 6: Organic Chemistry I · Topic 17: Organic Chemistry II · Topic 18: Organic Chemistry III
Question and mark scheme from the Edexcel A-Level Chemistry examination, Paper 2, June 2017. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.