4.6.3 · D5Polymers
Question bank — Condensation polymers — nylon-6,6, nylon-6, terylene (PET), bakelite, melamine, Kevlar
Before the questions, three words we will use constantly, each pinned to a plain picture so no symbol is unearned:
True or false — justify
Nylon-6,6 releases exactly 6 water molecules per chain.
False. It releases roughly one water per amide bond formed; for repeat units that is about waters, not a fixed 6. The two 6's count carbons in the monomers, not waters.
PET and nylon are both made by throwing out water, so they are the same class of polymer.
False. Both lose water, but the linkage differs: PET forms an ester () from acid + alcohol, nylon forms an amide () from acid + amine. Class is defined by the linkage, so PET is a polyester and nylon a polyamide.
A monomer with only one functional group cannot help build a long condensation chain.
True. With a single "hand" it reacts once and then has nothing left to continue — it caps the chain (a dead end), so it can only terminate, never extend.
Bakelite can be softened and re-moulded by heating.
False. Its three reactive sites on phenol build a 3-D cross-linked network — one giant molecule with no free chains to slide — so on heating it chars rather than melts. That is the definition of a thermoset.
In nylon-6, water is eliminated at every bond, exactly like nylon-6,6.
False. Nylon-6 comes from caprolactam by ring-opening; the ring simply opens and links, so no water is spat out at each join. It is still a polyamide because the repeat unit carries amide links.
Kevlar owes its strength mainly to strong covalent bonds along the backbone.
Misleading, so effectively false. The backbone bonds matter, but the exceptional strength comes from rigid aromatic chains packing straight plus extensive inter-chain hydrogen bonds holding sheets together.
Melamine and bakelite belong to the same structural family.
True. Both use a monomer with three reactive sites (three on melamine, three ring positions on phenol) that cross-link with formaldehyde into a hard 3-D thermoset network.
Every condensation polymer eliminates water.
False. The eliminated molecule is a small molecule, not always water — e.g. an acid-chloride route to Kevlar eliminates , and nylon-6 (ring-opening) eliminates essentially nothing per join.
Spot the error
"Adipic acid is , so it has 4 carbon atoms."
Wrong count. The two carboxyl carbons ( in each ) must be added to the four carbons → 6 total, which is exactly why nylon-6,6 has its second "6".
"Nylon-6,6 is made from ethylene glycol and adipic acid."
Wrong monomer. Ethylene glycol is an alcohol and belongs to PET. Nylon-6,6 needs an amine partner: hexamethylenediamine + adipic acid.
"PET's ester link forms because two groups combine."
Wrong mechanism. An ester needs one from the acid and one from the alcohol to leave as water; a carbon–oxygen bond then forms between the two different partners, not between two identical s.
"Bakelite is a thermoplastic because it's a plastic."
Wrong category. "Plastic" is casual language; the technical split is thermoplastic vs thermoset. Its 3-D network makes it a thermoset.
"Kevlar is a polyester because it contains benzene rings like PET."
Wrong linkage. Benzene rings appear in both, but Kevlar joins an acid to an amine → amide link, making it an aromatic polyamide (aramid), not a polyester.
"Caprolactam needs a second monomer to polymerise."
Wrong. Caprolactam is a ring already carrying both an and a , so it self-links; nylon-6 is famous for using a single monomer.
"Formaldehyde attacks phenol at the carbon bearing the group."
Wrong position. The activates the ring by Electrophilic aromatic substitution at the ortho and para positions (2 ortho + 1 para = three sites), not at the carbon already holding the oxygen.
Why questions
Why must a condensation monomer be at least bi-functional?
Because a chain needs to grow from both ends — two "hands" let each monomer hold a neighbour on each side; with one hand it would only ever cap.
Why does higher functionality (three sites) produce hardness and infusibility?
Three reactive directions weave a 3-D cross-linked net — a single giant molecule with no independent chains to slide past one another, so it cannot flow or melt.
Why is the repeat unit of a condensation polymer lighter than the sum of its monomers?
Because at each linkage a small molecule leaves (water/HCl), so that lost mass is missing from the repeat unit — the fingerprint that distinguishes condensation from addition polymers.
Why does aromaticity make Kevlar's chains stiff and rod-like?
The flat, rigid benzene rings resist rotation and bending, so the backbone stays straight and extended, letting chains line up and hydrogen-bond into strong sheets.
Why is water sometimes shown as a product in nylon-6 despite it being "ring-opening"?
A trace of water is used to open the first ring and start the reaction; it is catalytic/initiating, not stoichiometrically released at every join like in nylon-6,6.
Why can't nylon and PET form the same 3-D thermoset network as bakelite?
Their monomers are strictly bi-functional (two hands each), so they can only make linear chains — no third hand exists to cross-link into a net; hence they are thermoplastic fibres.
Why does removing the eliminated water actually drive the polymerisation forward?
Condensation is an equilibrium; taking away the water product pulls the reaction toward more bond formation (Le Chatelier), giving longer chains.
Edge cases
If you mixed adipic acid with a mono-amine (one ), what happens to the chain length?
The mono-amine acts as a chain-stopper — it caps whichever end it reaches, so chains stay short and no high polymer forms.
What if a small amount of a tri-functional monomer sneaks into a nylon batch?
The third "hand" introduces a branch/cross-link point, so the material shifts toward a network and loses the clean, meltable, fibre-drawing behaviour of a linear thermoplastic.
At the very start of any step-growth polymerisation, why is the chain still tiny even after many reactions?
Because pieces join any-to-any — mostly monomers joining into dimers and trimers first; long chains only appear near the end, when nearly all ends have reacted (this is characteristic step-growth behaviour).
Is nylon-6 chemically identical to nylon-6,6 because both contain amide links?
No. Both are polyamides, but nylon-6 has repeat unit from one monomer, while nylon-6,6 alternates a diamine and a diacid — different repeat structure, different packing and melting point.
If you polymerised terephthalic acid chloride with para-phenylenediamine instead of the acid, what small molecule leaves?
, not water — the acid chloride's leaves with the amine's ; it is still a condensation forming the same Kevlar amide link.
What limits how many reactive positions phenol can use with formaldehyde?
Phenol offers exactly three activated positions (two ortho, one para) via Electrophilic aromatic substitution; that hard cap of three is precisely what enables a 3-D net and no more.
If ethylene glycol (a diol) reacted with a mono-carboxylic acid, could you get terylene?
No. A single acid group can only form an ester at one end — you'd get a small ester, not a chain. Terylene needs the di-acid terephthalic acid so both ends can link.
Recall One-line self-test before you leave
- Class of PET, and why? ::: Polyester — acid + alcohol gives an ester link.
- Class of Kevlar, and why? ::: Polyamide (aramid) — acid + amine gives an amide link, aromatic monomers.
- The two thermosets here? ::: Bakelite and melamine–formaldehyde, both from tri-functional monomers.
- The odd nylon out, and why? ::: Nylon-6 — a single monomer (caprolactam) by ring-opening.