Polymers: Addition and Condensation
Learn and apply Polymers: Addition and Condensation in the published Chemistry course sequence.
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Addition and Condensation Polymers (H2): Orientation
Polymer questions are scoring questions if you follow the drawing rules: identify monomers, draw a correct repeat unit, and state whether a small molecule is eliminated. This lesson trains that “monomer ↔ repeat unit” translation for both addition and condensation polymers.
This topic gets cleaner if you cross-check Organic Mechanisms: Curly Arrows, Electrophiles, Nucleophiles while navigating from the Organic Chemistry hub.
Definitions (Must Know)
A. Polymer and monomer
- A monomer is a small molecule that can join to form a polymer.
- A polymer is a long-chain molecule made of repeating units.
B. Addition polymerisation
In addition polymerisation, monomers add together with no small molecule eliminated (commonly from alkenes).
C. Condensation polymerisation
In condensation polymerisation, monomers react and a small molecule is eliminated (often H₂O).
D. Repeat unit
A repeat unit is the smallest segment of a polymer chain that repeats along the chain (written in brackets with an n).
Detailed Explanations
A macromolecule contains about 10² or more atoms joined by covalent bonds. A typical polymer molecule contains roughly 10² or more repeating units and has a relative molecular mass of about 10³ or greater. These are scale descriptions, not a claim that every polymer chain has exactly the same length.
A. Addition polymer example (ethene → poly(ethene))
Monomer: CH₂ = CH₂
Repeat unit idea: [-CH₂-CH₂-]ₙ
What to write:
- “The C=C opens and forms single bonds between monomers; no by-product forms.”
Because addition polymerisation uses C=C monomers and no small molecule is eliminated, therefore you should not write H₂O or HCl as a by-product for addition polymers.
B. Condensation polymer examples
1) Polyester (diol + dicarboxylic acid)
General reaction idea:
- -OH reacts with -COOH to form an ester link -COO⁻ and water is eliminated.
2) Polyamide (diamine + dicarboxylic acid, or acyl chloride route)
General reaction idea:
- -NH₂ reacts with -COOH to form an amide link -CONH⁻ and water is eliminated.
C. Proteins and peptide bonds
A peptide bond forms between -NH₂ and -COOH of amino acids, eliminating H₂O.
Hydrolysis (concept):
- heat with aqueous acid or aqueous alkali to break peptide bonds by adding water. Acid hydrolysis gives protonated amino-acid products; alkaline hydrolysis gives carboxylate salts.
D. Workflow: drawing an addition polymer repeat unit (exam method)
- Identify the C=C in the monomer.
- Replace the C=C with a C–C single bond.
- Keep the substituents on the same carbon atoms.
- Put the repeat unit in brackets and add n.
Mini example: Ethene CH₂ = CH₂ → repeat unit [-CH₂-CH₂-]ₙ.
E. Workflow: identifying monomers for condensation polymers
- Identify the link in the polymer: ester -COO⁻ or amide/peptide -CONH⁻.
- “Cut” the link back into the functional groups that formed it:
- ester link → -COOH + -OH
- amide link → -COOH + -NH₂
- Ensure each monomer is difunctional so the chain can continue.
F. Recycling decisions
Recycling polymers involves linked environmental, economic and social choices:
- Environmental: it can reduce demand for fossil feedstocks and landfill, but collection, transport, washing and remelting also use energy and may produce emissions.
- Economic: clean, single-polymer streams are more valuable; mixed or contaminated waste can cost more to separate than the recycled material is worth.
- Social: convenient collection and clear labelling improve participation, while deposit schemes or regulations can change behaviour and cost distribution.
Mechanical recycling usually needs sorting by polymer type because different polymers soften at different temperatures and mixed products can have poor properties. Chemical recycling may recover monomers or useful feedstocks but often needs more energy. A balanced exam answer applies these trade-offs to the named polymer and process instead of stating that recycling is always automatically beneficial.
Worked Examples
Modelled example 1
Classify Poly(ethene) Formation
Problem
Study the worked solution
Inspect the monomer change
Method
Open the C=C bond in many ethene molecules.Reason
The monomers join directly into one carbon-chain macromolecule.Working
nCH₂ = CH₂ → [-CH₂-CH₂-]ₙ.Classify the process
Method
Name addition polymerisation.Reason
No small molecule is eliminated as the monomers join.Working
Poly(ethene) forms by addition polymerisation.
Guided practice 2
Diol plus Dicarboxylic Acid
Problem
Use monomer groups and coproduct
Hints
Hint 1: link chemistry
Hint 2: coproduct
View solution step by step
Identify the link
Method
Form ester links between diol and dicarboxylic-acid residues.Reason
Each monomer is bifunctional, allowing the chain to continue.Working
Repeated -COO⁻ links → polyester.Classify polymerisation
Method
Name condensation polymerisation.Reason
A small molecule, water, is eliminated during link formation.Working
Product: polyester; process: condensation polymerisation.
Common misconception 3
The Link in Proteins
Learner claim
Match monomer groups to linkage
View solution step by step
Identify the amino-acid groups
Method
React an amino group with a carboxyl group.Reason
The nitrogen-containing group distinguishes this linkage from an ester.Working
-NH₂ + -COOH.Name the link
Method
Name the resulting -CONH⁻ link as peptide or amide.Reason
Water elimination alone does not determine whether the link is ester or amide.Working
Protein link: peptide (amide) link.
Challenge 4
Chloroethene Repeat Unit
Representation transfer
Preserve atoms while opening C=C
Hints
Hint 1: backbone
Hint 2: substituent
View solution step by step
Open the alkene bond
Method
Convert the two alkene carbons into the saturated repeat-unit backbone.Reason
The former π bond supplies the new links between monomer units.Working
CH₂ = CHCl → -CH₂-CHCl⁻.Show the repeat unit
Method
Enclose the unit in brackets with continuation bonds and n.Reason
The chlorine substituent remains bonded to the same carbon.Working
[-CH₂-CHCl-]ₙ.
Mind Stretchers
Mind stretcher 1Extension
Give one reason why condensation polymers can be biodegradable in some cases.
Show Hint
Look for a bond in the backbone that water or an enzyme can cleave.
Show Answer
Mark scheme (any one):
- Condensation polymers often contain polar functional groups (ester/amide links) that can be hydrolysed.
- Enzymes can catalyse hydrolysis of certain links (e.g. peptide bonds in proteins).
Mind stretcher 2: Separating hydrolysability from biodegradabilityExtension
Question. Polymer A has only a carbon–carbon backbone. Polymer B contains ester links. Explain why B may be more biodegradable, then state why the link alone does not prove rapid degradation outdoors.
Show Hint
Separate chemical possibility from the rate under actual environmental conditions.
Show Answer
Ester links can be hydrolysed, whereas the carbon–carbon backbone of a poly(alkene) is comparatively inert. Polymer B therefore has a chemically cleavable route. Its outdoor degradation rate still depends on temperature, water access, microorganisms, crystallinity, thickness and other conditions, so an ester link does not guarantee rapid biodegradation.