Chapter 26
Organic Chemistry
(Polymers)
Organic Chemistry
• Petrochemicals:
• Compounds built from oil or natural gas.
“Synthetic”
– Examples:
Detergents, pesticides,
pharmaceuticals, cosmetics.
– Petrochemicals are also important starting materials for
the production of Plastics.
• Plastics: Paints, fabrics, rubber, insulation
materials, foams, glasslike substances, adhesives,
molding and structural materials.
Organic Chemistry
• Ethene: One of the most important builder
molecules for plastic polymers.
– Commonly known as “Ethylene.”
H
H
C
C
H
H
– Its double bond makes it highly reactive.
Organic Chemistry
• Addition Reaction:
– Production of Ethanol from Ethene.
H
H
C
C
Ethene
H
H
H H
+
+
H
O
water
H


H
C
C
H
H
Ethanol
O
H
Organic Chemistry
• Addition Reaction:
– Production of Ethanol from Ethene.
H
H C
H H
H
C
H
H
H
+
H
H
O
H
• Monomer
Organic Chemistry
– A small molecule that is the starting molecule for the
formation of a polymer.
– Monomers generally contain double bonds that break to
form long chain-like structures called polymers.
• Polymer
– An extremely large molecule, (usually 500-20,000 or
more repeating units), made by linking monomers
together.
Organic Chemistry
• Low Density Polymer
– Carbon polymer chains with many branches that
can move easily over each other.
(Saran wrap, plastic bags)
Organic Chemistry
• High Density Polymer
– Carbon polymer chains that are stretched out
and stacked on top of each other increases the
polymer’s strength.
(A plastic milk jug is a high-density polymer)
Organic Chemistry
• Cross-Linked Polymer
– Carbon branched chains that have been linked
together by aligning them perpendicular to each
other or by adding a substance to bind the
carbons.
(A pop bottle cap is a cross-linked polymer)
Addition Polymers
• Polymers formed by linking monomers.
Example: Formation of Polyethylene.
monomer
x
H
H
C
C
H
H
“ethylene”
polymer
( )x
H H H

C C
H H H
H H
H
C C
H
H H
H H
H H
C
C
C
C
H
H
H
H
Polyethylene
Addition Polymers
• Polymers formed by linking monomers.
Example: Formation of PVC.
monomer
x
H
H
C
C
H
Cl
Vinyl Chloride

polymer
( )x
H H
H H H H
C C C C
H H Cl Cl
H Cl
H H
H H
C
C
C
C
H
Cl H
Cl
PolyVinylChloride
Addition Polymers
• Polymers formed by linking monomers.
Example: Formation of Polystyrene, “Styrofoam”.
monomer
x
H
H
C
C
polymer
H

H H
H H
H H
C
C
C
C
H
“styrene”
( )x
H H
C
H
C
H
Polystyrene
“Styrofoam”
C
H
C
Condensation Polymers
• Polymers formed by linking monomers and losing
simple molecules like water (or acid) in the process.
Example: Production of Nylon.
1,6 - Hexanediamine
and
HHH HHH
H - N -C-C-C-C-C-C- N - H
(
H H HHHHH H
Sebacoyl Chloride
HH
HHH
HHHH
HH
HO
OH
Cl -C-C-C-C-C-C-C-C-C-C- Cl
H HHHHHHH
)x
HHH HHH
O H HH HHH HHO
- N -C-C-C-C-C-C- N - C-C-C-C-C-C-C-C-C-CH HHHHHHH
H H HHHHH H
Amide group
+
Nylon (a polyamide)
Acid
Protein chains: Biological polymers
• Amino Acid
– A small molecule that is the starting molecule for the formation
of protein chains.
– Basic amino acid contain the amine group and the carboxylic acid
group.
H
N
H
O
C
C O-H
H H
Glycine is the basic amino acid.
• Fatty Acids
Fatty acids
– Long hydrocarbon chains that end with
the acid group.
H
H
H H H H H H H H H H H H
O
C
C C C C C C C C C C C C
H H H H H H H H H H H H
C O-H
H
CH3(CH2)12COOH
Lauric acid is a fatty acid
(see pg.789 for more)
Fatty acids
CH3CH2COOH
CH3(CH2)4COOH
IUPAC Name
Common name
Propanoic acid “Proprionic acid”
1st fatty acid (see pg.789)
CH3(CH2)6COOH
Butanoic acid “Butyric acid”
“Stinky feet smell”
Hexanoic acid “Caproic acid”
CH3(CH2)10COOH
Decanoic acid “Capric acid”
CH3(CH2)12COOH
Dodecanoic acid “Lauric acid”
CH3(CH2)16COOH
Hexadecanoic acid “Palmitic acid”
CH3(CH2)18COOH
Octadecanoic acid “Stearic acid”
Inexpensive candles
made from beef fat.
Typical Fat
• Triglycerides
– When fatty acids are combined with glycerol.
H
H Water is made
O
C
C
O H
H-O
O
H
C
O H
H-O
C
(CH2)18CH3
(CH2)18CH3
O
H
C
O H
H
Glycerol
H-O
C
(CH2)18CH3
Fatty acids: “Stearic acid”
Trigylceride: “Typical Fat”
H
H
C
O
-O
C
O
H
C
-O
C
(CH2)18CH3
(CH2)18CH3
O
H
C
H
-O
C
(CH2)18CH3