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 question

Question

A multi-part organic chemistry question about polymerisation and stereoisomerism. Part (a) asks to draw two repeat units for addition polymers from but-1-ene and cyclohexene. Part (b) asks to deduce monomers for a given polyamide. Part (c) asks for a single monomer for a given cyclic/internal amide. Part (d) covers 2-hydroxypropanoic acid enantiomers, how to distinguish them in a lab, and the advantage of biodegradable polyesters.
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 The mark scheme provides accepted structures for the addition polymers with two repeat units, formulas for the monomers needed to form the polyamides, 3D representations using wedges and dashes for the two enantiomers of 2-hydroxypropanoic acid, and answers regarding plane-polarised light and environmental accumulation for the remaining parts.

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.

Question Part (a) - Addition 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!
Mark breakdown: 1 mark for the correct 2-repeat unit structure of poly(but-1-ene); 1 mark for poly(cyclohexene).
Question Part (b) - Polyamide Monomers

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.
Mark breakdown: 1 mark for the dicarboxylic acid (or acyl chloride); 1 mark for the diamine.
Question Part (c) - Single Monomer Polyamide

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.

Mark breakdown: 1 mark for the correct amino acid formula.
Question Part (d)(i) - Stereoisomerism

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 .
Mark breakdown: 1 mark for correct 3D tetrahedral setup; 1 mark for correctly showing the non-superimposable mirror image pair.
Question Part (d)(ii) - Analytical Chemistry

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).

Mark breakdown: 1 mark for mentioning rotation of plane-polarised light.
Question Part (d)(iii) - Environmental Chemistry

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.

Mark breakdown: 1 mark for stating reduction in landfill accumulation or environmental persistence.

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.