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35
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20 Frequency
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Bin
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 Synthetic and Biological Polymers

Polymers: Macromolecules formed by the covalent

attachment of a set of small molecules termed monomers.

Polymers are classified as:

(1) Man-made or synthetic polymers that are
synthesized in the laboratory;
(2) Biological polymer that are found in nature.

Synthetic polymers: nylon, poly-ethylene, poly-styrene

Biological polymers: DNA, proteins, carbohydrates

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 Methods for making polymers

Addition polymerization and condensation polymerization

Addition polymerization: monomers react to form a

polymer without net loss of atoms.

Most common form: free radical chain reaction of

ethylenes

n monomers one polymer molecule

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Example of addition polymers

4
Free-Radical AdditionPolymerization of
Ethylene
H2C CH2

200 °C O2
2000 atm peroxides

CH2 CH2 CH2 CH2 CH2 CH2 CH2

polyethylene
Free-Radical Polymerization of Propene

H2C CHCH3

CH CH CH CH CH CH CH
CH3 CH3 CH3 CH3 CH3 CH3 CH3

polypropylene
 ..
RO
.. • Mechanism
H2C CHCH3
 ..
RO: Mechanism
H2C CHCH3
•
 ..
RO: Mechanism
H2C CHCH3
•

H2C CHCH3
 ..
RO: Mechanism
H2C CHCH3

H2C CHCH3
•
 ..
RO: Mechanism
H2C CHCH3

H2C CHCH3
•

H2C CHCH3
 ..
RO: Mechanism
H2C CHCH3

H2C CHCH3

H2C CHCH3
•
 ..
RO: Mechanism
H2C CHCH3

H2C CHCH3

H2C CHCH3
•

H2C CHCH3
 Likewise...

•H2C=CHCl polyvinyl chloride

•H2C=CHC6H5 polystyrene

•F2C=CF2 Teflon
Important
constitutions
for synthetic
polymers

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Supramolecular
structure of
polymers

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Structural
properties of
linear
polymers:
conformationa
l flexibility
and strength

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Cross linking adds
tensile strength

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 Condensation polymerization

Condensation polymerization: the polymer grows from

monomers by splitting off a small molecule such as
water or carbon dioxide.

Example: formation of amide links and loss of water

Monomers

First unit of polymer + H2O

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 Polymers in the movies

In the 1967 movie, "The Graduate”,

a smug Los Angeles businessman takes aside the

baby-faced
Dustin Hoffman and declares,

"I just want to say one word to you -- just

one word -- 'plastics.' "

In 2005 we can replace ‘plastics’ with

another word: ‘synthetic polymers’
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Rembember from GChem?

Nylon is a condensation polymer

made of the monomers adipic acid
and hexamethylene diamine.

O OH
O

OH
Q uickTim e™ and a
Phot o - JPEG decom pr essor
ar e needed t o see t his pict ur e.

They're nylons, Benjamin.

adipic acid
+
NH2
H2N

hexamethylene diamine

nylon
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 Hydrogen bonds between chains

Supramolecular
Structure of
nylon

Intermolecular
hydrogen bonds
give nylon
enormous tensile
strength

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 Biopolymers

Nucleic acid polymers (DNA, RNA)

Amino acids polymers (Proteins)

Sugar polymers (Carbohydrates)

Genetic information for the cell: DNA

Structural strength and catalysis: Proteins

Energy source: Carbohydrates

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 Proteins: amino acid monomers

The basic structure of an amino acid monomer

HO NH2
H
O R

The difference between amino acids is the R group

25
 Proteins: condensation polymers

Formed by condensation polymerization of amino acids

Monomers: 20 essential amino acids

NH2 General structure of an amino acid
H R
CO2H R is the only variable group

Glycine (R = H) + Glycine First step toward poly(glycine)

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Representation of the
constitution of a protein

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Three D representation of the structure of a protein

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DNA
 Thymine (T)
The monomers:

Adenine (A)
Cytosine (C)

Guanine (G)

Phosphate-
Sugar (backbone) of
DNA
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Phosphate-
sugar
backbone
holds the DNA
macromolecule
together

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One strand
unwinds to
duplicate its
complement via a
polymerization of
the monomers
C, G, A and T

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Carbohydrates
34