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4.3.5Core Organic Chemistry

Polymers from Alkenes

5 min read 6 parts Lesson 15 of 29 Virtual lab

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Part 1 of 6Addition Polymerisation

4.3.5 Polymers from Alkenes

The polymer name is poly followed by the monomer name in brackets.

Monomer
  • Alkene molecules with a C=C bond act as the monomers that join in a long chain.
Process
  • The π bond in each monomer breaks and the molecules link by σ bonds to form a long saturated chain.
Repeat unit
  • The repeat unit is the part of the polymer chain that repeats, drawn with open bonds on both sides.
Only one product
  • All atoms of the monomer end up in the polymer, so addition polymerisation has a 100% atom economy.
Examples
  • Ethene gives poly(ethene), propene gives poly(propene) and chloroethene gives poly(chloroethene), also called PVC.

Part 2 of 6Drawing Repeat Units

1
Draw the monomer so that the C=C is in the centre, with other groups above and below.
2
Replace the double bond with a single bond, keeping the groups as they were.
3
Add a bond that extends outward from each carbon, shown through the end brackets of the repeat unit.
4
For poly(propene) the repeat unit is –CH₂–CH(CH₃)–, from the propene CH₂=CHCH₃.
5
To find the monomer from a polymer, take one repeat unit and put the double bond back between the two chain carbons.

Part 3 of 6Properties and Uses

Properties and Uses
Chemically inert
  • The long chains of strong, non-polar C–C and C–H bonds resist attack by most reagents.
Intermolecular forces
  • Chains attract each other by London forces, with stronger polar forces in polymers like PVC that contain C–Cl bonds.
Uses
  • Poly(ethene) makes bags and bottles, poly(propene) makes crates and ropes, and PVC makes pipes and window frames.
Persistence
  • Because they are inert, addition polymers are not biodegradable and can persist in the environment for a long time.
MonomerPolymerRepeat unit
Ethene, CH₂=CH₂Poly(ethene)–CH₂–CH₂–
Propene, CH₂=CHCH₃Poly(propene)–CH₂–CH(CH₃)–
Chloroethene, CH₂=CHClPoly(chloroethene)–CH₂–CHCl–

Part 4 of 6Disposal and Recycling

Landfill
  • Burying polymer waste uses land and the polymers do not break down, so it is a poor long-term option.
Incineration
  • Burning polymers can release energy for heating or electricity but produces carbon dioxide and, for PVC, toxic hydrogen chloride.
Recycling
  • Polymers can be sorted, melted and remoulded, saving raw materials but requiring careful separation.
Feedstock recycling
  • Heating polymers breaks them down into monomers or other small molecules which can be reused to make new plastics.
Biodegradable alternatives
  • Polymers designed to break down reduce waste, though conditions for decomposition may not be met in all disposal routes.

Part 5 of 6Worked Example

Question

  • A sample of poly(chloroethene) has a relative molecular mass of 62 500.
  • How many repeat units does one chain contain?
  • (Ar: H = 1.0, C = 12.0, Cl = 35.5)

  1. The monomer is chloroethene, C₂H₃Cl, and the repeat unit has the same formula.
  2. Mr of repeat unit = 2 × 12.0 + 3 × 1.0 + 35.5 = 62.5.
  3. Number of repeat units = 62 500 / 62.5.
  4. = 1000.

Answer 1000 repeat units

Part 6 of 6Exam Checklist & Tips

4.3.5 – Key Points for the Exam

  • Addition polymer A long chain molecule formed when many alkene monomers join without losing any atoms.
  • Monomer A small molecule that can be joined with others to form a polymer.
  • Repeat unit The section of the polymer chain that repeats along its length.
  • Feedstock recycling Breaking polymers into small molecules that can be used as raw materials.

Common Mistakes

  • Leaving the C=C double bond in the repeat unit; it becomes a single bond.
  • Forgetting the extension bonds through the brackets of the repeat unit.
  • Stating that addition polymers are biodegradable because they are 'organic'.
  • Drawing the repeat unit with only the two chain carbons and omitting side groups.
Try it in the virtual labCracking of hydrocarbons \n