Understanding Polymerization: Addition
vs. Condensation
1. Introduction: Building Giant Molecules
Imagine you have a big box of individual paper clips. Each clip is a single, small unit. By
linking them together, one after another, you can create a long, flexible chain. In the world of
chemistry, this is the fundamental concept behind polymers.
The individual "clips" are small, simple molecules called monomers. When many of these
monomers are chemically bonded together in a repeating pattern, they form a very large
molecule called a polymer. These giant molecules are the building blocks for materials we
use every day, from plastics to natural fibers.
This explainer will introduce you to the two primary chemical processes used to link these
monomers into polymer chains: Addition Polymerization and Condensation
Polymerization.
2. Addition Polymerization: Just Adding Up
The "All-In" Method: No Atoms Left Behind
Addition polymerization is a process where many monomer molecules join together to form a
single, long-chain polymer. The key feature of this method is that no other substance is
produced in the reaction—the polymer is the only product.
For a monomer to undergo addition polymerization, it must have one critical feature: a
carbon-carbon double bond (C=C). During the reaction, one of the bonds in each C=C
bond breaks, allowing the monomers to link end-to-end and form a long chain saturated with
single bonds.
Key Characteristics of Addition Polymerization:
Monomer Type: Must contain a C=C double bond (like an alkene).
Reaction: One of the bonds in the double bond breaks, allowing monomers to link
end-to-end.
Product: Only one product is formed – the polymer. No atoms are lost.
A classic example is the formation of poly(ethene) from ethene monomers. Ethene is an
alkene with a C=C double bond. When many ethene molecules react, their double bonds open
up, and they link together to form the long-chain polymer, poly(ethene).
Notice the naming convention: we place the name of the monomer in brackets and add the
prefix "poly-".
While addition reactions simply combine monomers, condensation reactions involve a more
complex exchange.
3. Condensation Polymerization: Joining with a Loss
The "Give and Take" Method: Making Room for the Bond
Condensation polymerization is the second major method of forming polymers. Its defining
characteristic is that when monomers join, a small molecule—usually water—is eliminated
or "lost" for each bond that forms. This is the primary difference from addition
polymerization.
Monomers suitable for this process must have two functional groups, one at each end of the
molecule. This process typically involves two different types of monomers reacting together,
with the functional group of one reacting with the functional group of the other. Examples of
these functional groups include the carboxylic acid group (-COOH), the amine group (-NH2),
and the alcohol group (-OH).
Key Characteristics of Condensation Polymerization:
Monomer Type: Typically involves two different monomers, each with two
functional groups (e.g., a dicarboxylic acid with two -COOH groups and a diamine
with two -NH2 groups, or a diol with two -OH groups).
Reaction: The functional groups at the ends of the monomers react to form a link.
Products: Two products are formed – the polymer AND a small molecule (like
water) for each link created.
Two important synthetic polymers are made this way:
1. Nylon: A type of polyamide. It is formed from the reaction between a dicarboxylic
acid monomer (containing two carboxylic acid, -COOH, groups) and a diamine
monomer (containing two amine, -NH2, groups). The link formed is called an amide
linkage, and a molecule of water is lost for each link.
2. PET (Terylene): A type of polyester. It is formed from a dicarboxylic acid
monomer and a diol monomer (containing two alcohol, -OH, groups). The link
created is an ester linkage. For every ester linkage formed, one molecule of water is
eliminated from the combination of a proton (H+) from a -COOH group and a
hydroxyl ion (OH–) from an -OH group.
Nature also uses this method in profound ways. Proteins are essential biological molecules
that serve as a perfect example of a natural polyamide. Just like nylon, they are formed via
condensation polymerization and feature amide linkages. However, instead of two different
monomer types, proteins are built from amino acid monomers, which uniquely contain both
an amine group (-NH2) and a carboxylic acid group (-COOH) in the same molecule. When
these amino acids polymerize, they form the same amide links seen in synthetic nylon,
demonstrating how the same fundamental chemical principles build both industrial materials
and the molecules of life itself.
Now that we've seen each process individually, let's put them side-by-side to make the
differences crystal clear.
4. At a Glance: Key Differences Summarized
This table provides a quick reference to highlight the fundamental distinctions between the
two types of polymerization.
Feature Addition Polymerization Condensation Polymerization
Must have two functional groups at
Monomer
Must contain a C=C double bond. each end (e.g., -COOH, -OH, -
Requirement
NH2).
One of the bonds in the C=C double
How Monomers Functional groups react together,
bond breaks to form new single
Join forming a link.
bonds.
By-products Yes. A small molecule (usually
None. Only the polymer is formed.
Formed water) is lost per link.
Nylon (a polyamide), PET/Terylene
Example(s) Poly(ethene)
(a polyester), Proteins
5. Conclusion: Two Paths to a Polymer
Understanding addition and condensation polymerization gives you insight into the two
fundamental chemical pathways for creating the giant molecules that make up so many
materials around us. From simple plastics to complex proteins, these processes are key to
building long molecular chains from small monomer units.
The easiest way to remember the difference is that in addition, all the atoms from the
monomers are present in the final polymer. In condensation, a small molecule like water is
released for every new bond that forms the polymer chain.
Study Guide: Polymers, Polymerization,
and Environmental Impact
This guide provides a comprehensive review of polymers, including their formation through
addition and condensation polymerization, key examples like nylon and PET, and the
environmental implications of their disposal and recycling.
Short-Answer Quiz
Answer each question in 2-3 sentences based on the provided context.
1. What is a polymer, and what are the smaller molecules that form it called?
2. Describe the process of addition polymerization using ethene as an example.
3. What key chemical feature must a monomer possess to undergo addition
polymerization?
4. In terms of products, what is the fundamental difference between addition and
condensation polymerization?
5. Identify the types of monomers and the chemical linkage formed during the creation
of nylon.
6. What is PET, and what two functional groups react to form its characteristic linkage?
7. Explain why proteins are classified as natural polyamides.
8. What does it mean for a polymer to be non-biodegradable, and why is this a problem
for landfills?
9. List two significant environmental hazards associated with the incineration of plastic
waste.
10. Describe the process of PET re-polymerization and explain its primary environmental
benefit.
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Quiz Answer Key
1. A polymer is a large molecule that is built up from many smaller, repeating molecules
called monomers. These monomers join together in long chains, linked by covalent
bonds.
2. In the addition polymerization of ethene, the carbon-carbon double bond (C=C)
within each ethene monomer breaks. The monomers then link together to form a long-
chain polymer called poly(ethene), which contains only single bonds and is the sole
product of the reaction.
3. To undergo addition polymerization, a monomer must contain a carbon-carbon double
bond (C=C). During the polymerization process, one of the bonds in this double bond
breaks, allowing the monomer to form a single bond with an adjacent monomer.
4. The fundamental difference is that addition polymerization forms only one product:
the polymer molecule itself. In contrast, condensation polymerization forms the
polymer molecule as well as a small molecule, typically water, which is eliminated
for each bond formed between monomers.
5. Nylon is a polyamide formed from two different types of monomers: a dicarboxylic
acid, which has a -COOH group at each end, and a diamine, which has an -NH2 group
at each end. These monomers react to form a repeating amide linkage.
6. PET, or polyethylene terephthalate, is a polyester formed from dicarboxylic acid
monomers and diol (alcohol) monomers. The carboxylic acid functional group (-
COOH) on one monomer reacts with the alcohol functional group (-OH) on the other
to form an ester linkage.
7. Proteins are considered natural polyamides because they are naturally occurring
polymers formed from amino acid monomers. These monomers are joined by amide
links (also known as peptide links) through a condensation reaction, similar to the
formation of synthetic polyamides like nylon.
8. A non-biodegradable polymer is one that cannot be broken down by microorganisms
like decomposers because it is chemically unreactive. This is a problem for landfills
because the plastic waste accumulates without decomposing, causing the sites to fill
up quickly.
9. When plastics are incinerated, they release carbon dioxide, a greenhouse gas that
contributes to climate change. Additionally, some polymers like poly(vinylchloride)
can release toxic fumes such as hydrogen chloride gas, and incomplete combustion
can produce toxic carbon monoxide.
10. PET can be broken down (depolymerized) into its original monomers using enzymes
or chemical catalysts under mild conditions. These monomers are then recovered and
can be re-polymerized to create new PET. The primary benefit is that this process
saves resources and energy, reducing the carbon footprint of production.
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Essay Questions
Construct detailed responses to the following prompts, incorporating specific examples and
chemical principles from the source material.
1. Compare and contrast the chemical processes, monomer requirements, and products
of addition polymerization and condensation polymerization. Use specific synthetic
polymers such as poly(ethene) and PET to support the discussion.
2. Discuss the environmental challenges presented by the widespread use and disposal of
synthetic polymers. Evaluate the advantages and disadvantages of the primary
disposal methods, including landfills and incineration.
3. Explain the chemical basis for classifying both nylon and proteins as polyamides.
Describe the specific monomers and linkages involved in each, highlighting the key
similarities and differences between these synthetic and natural polymers.
4. Analyze the lifecycle of a PET plastic bottle, from the condensation polymerization of
its monomers to its potential for recycling. Explain why the ability to re-polymerize
PET is a significant advancement in managing plastic waste.
5. Starting with an alkene monomer such as propene, detail the step-by-step process of
forming an addition polymer. Explain the conventions for naming the resulting
polymer and drawing its repeating unit, ensuring all required notations are included.
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Glossary of Key Terms
Term Definition
A polymer formed by the joining up of many monomers, typically
Addition polymer
those containing C=C bonds.
A reaction where monomers with C=C double bonds break one of
Addition
their bonds to join together, forming a long-chain polymer. This
polymerisation
process forms only one product.
A type of organic molecule that contains a carbon–carbon double
Alkene
bond (C=C).
The chemical link formed when a -COOH group reacts with an -NH2
Amide linkage group. This is the characteristic linkage in polyamides like nylon and
proteins.
Small molecules that are the monomers of proteins. They contain
Amino acid both an amine (-NH2) and a carboxylic acid (-COOH) functional
group.
A carbon-carbon double bond, the key functional group required for a
C=C bond
monomer to undergo addition polymerization.
Condensation A polymer formed when two different monomers are linked together
polymer with the removal of a small molecule, usually water.
Condensation A reaction that forms a polymer molecule and eliminates one small
polymerisation molecule (usually water) per linkage created between monomers.
The type of chemical bond that joins monomers together to form a
Covalent bonds
polymer chain.
A monomer with an amine (-NH2) group at each end, used in the
Diamine
formation of nylon.
A monomer with a carboxylic acid (-COOH) group at each end, used
Dicarboxylic acid
to make polyamides (like nylon) and polyesters (like PET).
An alcohol monomer with a hydroxyl (-OH) group at each end, used
Diol
in the formation of polyesters like PET.
The chemical link formed when a -COOH group reacts with an -OH
Ester linkage
group. This is the characteristic linkage in polyesters.
An alkene monomer used to form poly(ethene) through addition
Ethene
polymerization.
Monomer Small molecules that are the repeating building blocks of polymers.
A term for proteins, which are naturally occurring polymers formed
Natural polyamides
from amino acid monomers joined by amide (peptide) links.
The property of a substance, such as many plastics, that prevents it
Non-biodegradable
from being broken down by microorganisms.
A synthetic polyamide made from dicarboxylic acid and diamine
Nylon
monomers linked by amide bonds.
PET (polyethylene A common condensation polymer and type of polyester made from
terephthalate) dicarboxylic acid and diol monomers.
The specific name for the amide links that join amino acid monomers
Peptide links
together in proteins.
Plastics Materials made from polymers.
A type of polymer, such as nylon or protein, characterized by
Polyamide
repeating amide linkages.
A type of polymer, such as PET or terylene, characterized by
Polyester
repeating ester linkages.
An addition polymer formed from the polymerization of ethene
Poly(ethene)
monomers.
A large molecule built up from many smaller repeating molecules
Polymer
called monomers.
An addition to the beginning of a word. In polymer nomenclature,
Prefix
"poly-" is added as a prefix to the name of the monomer.
A natural condensation polymer formed from amino acid monomers
Protein
joined by peptide (amide) links.
The process of polymerizing monomers that have been recovered
Re-polymerisation
from the breakdown of an existing polymer, such as PET.
The section of a polymer's structure that is repeated to form the long
Repeat unit
chain. It is displayed in brackets with continuation bonds.
A small 'n' written on the bottom right-hand side of a polymer's repeat
Subscript n
unit to indicate a large, unspecified number of repeat units.
Terylene The trade name for PET when it is used in synthetic fibres.