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"I am inclined to think that the
development of polymerization
is perhaps the biggest thing that
chemistry has done, where it has
had the biggest effect on
everyday life
Lord Todd,1980
Ethylene Polyethylene
CH
2
= CH
2
[-CH
2
- CH
2
-]
n
Magic ?
USE NATURAL SYNTHETIC
Fibers Wool, Silk,
Cellulose
Nylon, PET,
Lycra
+
Molecule
Does not form NaCl molecule!
C
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C C C
H
H
H H
C
C
H
H
H C
H
H
H
C C C
H
H
C
H
H
CH
4
C
2
H
6
C
2
H
4
SSS Sooo ommm meee e BBB Baaa asss siii iccc c CCC Chhh heee emmm miii isss sttt trrr ryyy y::: :
FFF Fuuu unnn nccc cttt tiii iooo onnn naaa alll l GGG Grrr rooo ouuu uppp psss s
Functional Groups are small groups of atoms held together in a specific
arrangement by covalent bonds. They are responsible for the principle chemical
properties of the molecule in which they are found.
CH
2
=CH
2
ROH RCOH
=
O
RCOR
=
O
RNH
2
RCOH
=
O
RCNHR
=
O
+
+
Alcohol Carboxylic Acid Ester
Carboxylic Acid Amine Amide
Ethylene
CC
C C
oo
o o
nn
n n
dd
d d
ee
e e
nn
n n
ss
s s
aa
a a
tt
t t
ii
i i
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o o
nn
n n
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
ii
i i
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nn
n n
ss
s s
Acetic Acid Ethyl Alcohol
or Ethanol
Reversible
Reaction!
Ethyl Acetate
If you dont
know what this
is you should
be castigated
unmercifully
Ester linkage
CH
3
- C - OH + CH
3
- CH
2
- OH CH
3
- C - O - CH
2
- CH
3
+ H
2
O
O O
WW
W W
hh
h h
yy
y y
dd
d d
oo
o o
MM
M M
oo
o o
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l l
ee
e e
cc
c c
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ll
l l
ee
e e
ss
s s
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
??
? ?
CH
3
- C - OH
O
HO - CH
2
- CH
3
Acetic Acid
kersplat!
Ethyl Alcohol
or Ethanol
WW
W W
hh
h h
yy
y y
dd
d d
oo
o o
MM
M M
oo
o o
ll
l l
ee
e e
cc
c c
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l l
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e e
ss
s s
RR
R R
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aa
a a
cc
c c
tt
t t
??
? ?
H:O - CH
2
- CH
3
CH
3
- C:OH
O
HO
.
+
.
H HO:H ~ H
2
O
CH
3
- C
.
+
.
O - CH
2
- CH
3
CH
3
- C:O - CH
2
- CH
3
OO O
This isnt what really happens, but shows you
how the valency electrons get rearranged
MM
M M
aa
a a
kk
k k
ii
i i
nn
n n
gg
g g
aa
a a
PP
P P
oo
o o
ll
l l
yy
y y
mm
m m
ee
e e
rr
r r
Acetic Acid Ethyl Alcohol
or Ethanol
Reversible
Reaction!
Ethyl Acetate
Ester linkage
CH
3
- C - OH + CH
3
- CH
2
- OH CH
3
- C - O - CH
2
- CH
3
+ H
2
O
O O
If we heat acetic acid and ethanol up to just over 100
0
C,
to get the reaction going and drive off water, why dont
we form polymer?
Glycerol
CH
2
OHCHOHCH
2
OH
Nitroglycerin
C
C
C
C
C
C
O
O
O
O
O
O
O O
O
O O
O
N
N
N
EE
E E
xx
x x
pp
p p
ll
l l
oo
o o
ss
s s
ii
i i
vv
v v
ee
e e
SS
S S
tt
t t
uu
u u
ff
f f
ff
f f
!!
! !
GG
G G
uu
u u
nn
n n
cc
c c
oo
o o
tt
t t
tt
t t
oo
o o
nn
n n
aa
a a
nn
n n
dd
d d
CC
C C
oo
o o
ll
l l
ll
l l
oo
o o
dd
d d
ii
i i
oo
o o
nn
n n
GG
G G
uu
u u
nn
n n
cc
c c
oo
o o
tt
t t
tt
t t
oo
o o
nn
n n
aa
a a
nn
n n
dd
d d
CC
C C
oo
o o
ll
l l
ll
l l
oo
o o
dd
d d
ii
i i
oo
o o
nn
n n
PP
P P
aa
a a
rr
r r
kk
k k
ee
e e
ss
s s
aa
a a
nn
n n
dd
d d
PP
P P
aa
a a
rr
r r
kk
k k
ee
e e
ss
s s
ii
i i
nn
n n
ee
e e
He wasnt this
miserable.
TT
T T
hh
h h
ee
e e
CC
C C
rr
r r
yy
y y
ss
s s
tt
t t
aa
a a
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l l
PP
P P
aa
a a
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aa
a a
cc
c c
ee
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HH
H H
yy
y y
aa
a a
tt
t t
tt
t t
aa
a a
nn
n n
dd
d d
tt
t t
hh
h h
ee
e e
EE
E E
ll
l l
ee
e e
pp
p p
hh
h h
aa
a a
nn
n n
tt
t t
ss
s s
CCC Ceee elll llll luuu ulll looo oiii iddd d
What a sales pitch
CCC Chhh haaa arrr rddd dooo onnn nnnn neee ettt t aaa annn nddd d MMM Mooo ottt thhh heee errr r--- -iii innn n--- -LLL Laaa awww w SSS Siii illl lkkk k
O
HO
OH
O
CH
2
OH
CH
2
ONa
O
HO
OH
O
O
HO
OH
O
CH
2
OCSNa
S
CH
2
OH
O
HO
OH
O
NaOH
CS
2
H
+
RR
R R
ee
e e
gg
g g
ee
e e
nn
n n
ee
e e
rr
r r
aa
a a
tt
t t
ee
e e
dd
d d
CC
C C
ee
e e
ll
l l
ll
l l
uu
u u
ll
l l
oo
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ss
s s
ee
e e
CCC Ceee elll llll looo oppp phhh haaa annn neee e aaa annn nddd d RRR Raaa ayyy yooo onnn n
MMM Mooo orrr reee e
CCC Ceee elll llll looo oppp phhh haaa annn neee e
RRR Raaa ayyy yooo onnn n
BBB Baaa aeee ekkk keee elll laaa annn nddd d aaa annn nddd d BBB Baaa akkk keee elll liii ittt teee e
The first true synthetic plastic
A Bakelite telephone
A Bakelite microphone A Bakelite camera
Clear Bakelite items
A Bakelite radio
Clock made of a phenolic resin
and celluloid
BBB Baaa akkk keee elll liii ittt teee e --- - MMM Maaa attt teee errr riii iaaa alll l ooo offf f aaa a TTT Thhh hooo ouuu usss saaa annn nddd d UUU Usss seee esss s
NN
N N
ee
e e
tt
t t
ww
w w
oo
o o
rr
r r
kk
k k
FF
F F
oo
o o
rr
r r
mm
m m
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
OH
CH
2
OH
OH
CH
2
OH
CH
2
CH
2
OH
CH
2
OH
OH OH
CH
2
CH
2
OH
+ CH
2
O
*
*
* *
The hydrogens in the ortho and para positions to
the OH group, which by convention are not
usually shown but here are indicated by a , can
react with fomaldehyde to form (initially)
oligomers.
OH
H
H
H
H H
OH
H
H
H
H H
H
H
O
H H
O
OH
H
H
H
H H
AA
A A
CC
C C
oo
o o
nn
n n
dd
d d
ee
e e
nn
n n
ss
s s
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
ii
i i
oo
o o
nn
n n
!!
! !
OH
CH
2
O
H
2
C
CH
2
HO
OH
CH
2
CH
2
OH
CH
2
HO
CH
2
OH
CH
2
CH
2
O
OH
CH
2
CH
2
OH
O
CH
2
HO
CH
2
CH
2
OH
CH
2
CH
2
OH
HO
CH
2
HO
CH
2 CH
2
H
2
C
HO
NN
N N
ee
e e
tt
t t
ww
w w
oo
o o
rr
r r
kk
k k
FF
F F
oo
o o
rr
r r
mm
m m
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
Continued reaction
builds up a densely
cross-linked network.
This is Bakelite, a
thermosetting
polymer. Once the
reaction is complete,
the material cannot
be reheated and
reformed. So, what do
you think the
definition of a
thermoplastic is?
NNN NEEE EXXX XTTT T;;; ;
SSS Sttt taaa auuu uddd diii innn nggg geee errr r aaa annn nddd d ttt thhh heee e
MMM Maaa accc crrr rooo ommm mooo olll leee eccc cuuu ulll laaa arrr r
HHH Hyyy yppp pooo ottt thhh heee esss siii isss s