1) General

Alkenes are unsaturated hydrocarbons with general formula C

n
H
2n
Cycloalkenes are unsaturated hydrocarbons with general formula C
n
H
2n-2
Unsaturated = contain a double C=C bond
Hydrocarbon = contains C and H only
2) Bonding in Alkenes
o The carbons at either end of the double bond and the 4 atoms they are bonded to are
all in a plane !at"# These $ atoms are %oined by single bonds
o The bonds around each C in the C=C bond are trigonal planar in shape# There are &
areas of electrons round each C ' double bond and 2 single bonds" which repel e(ually
to gi)e a bond angle of '2*
o The double bond is formed by sideways o)erlap of p orbitals producing a bond
sausage-shaped clouds of electrons abo)e and below the plane of the single bond
framework"
3) E/Z isomers
+somers
,,,,,,,,,,,,,,,,,,,

-tructural -tereoisomers
+somers ,,,,,,,,,,,,,

./0 isomers 1ptical isomers A2 only"
-tereoisomers ha)e the same structural formula but with a di2erent arrangement in
space
./0 isomerism is one type of stereoisomerism arising from restricted rotation about a
double bond when two di2erent groups are attached to each carbon of the C=C group
. is short the 3erman word entgegen which means opposite i#e# on opposite sides of
the double bond
0 is short for the 3erman word zusammen which means together i#e# on the same side
of the double bond
'-bromo-2-chloropropene displays ./0 isomerism# This is because one C of the C=C
bond is attached to an H and a 4r5 which are di2erent5 and the other C of the C=C is
attached to a Cl and a CH
&
which are also di2erent
0-'-bromo-2-chloropropene .-'-bromo-2-chloropropene
6or an e7ample like this you only need to say that it will ha)e . and 0 isomers5 not
which one is which
4ut-2-ene is a simpler e7ample where it is more straightforward to say which is . and
which is 0
0-but-2-ene .-but-2-ene
CH
&
8s are together" CH
&
8s on opposite sides of the double bond"
Cis/trans isomerism is a special case of ./0 isomerism in which two of the substituent
groups are the same# Cis corresponds to 0 and trans corresponds to .
-ticking with but-2-ene as the e7ample
Cis-but-2-ene trans-but-2-ene
4) Addition Reactions of Alkenes
+n addition reactions5 2 molecules %oin to form ' molecule#
Alkenes undergo addition reactions because they ha)e a double bond#
a) Addition of hydrogen prodces an alkane
e#g# !"
2
#!"
2
$ "
2
!"
3
!"
3
ethane
9eeds a 9i catalyst
1ne mole of hydrogen needed per double bond
This reaction is used to produce margarine from unsaturated )egetable oils by
catalytic hydrogenation
%) Addition of halogens prodces a dihalogenoalkane
e#g# !"
2
#!"
2
$ Br
2
!"
2
Br!"
2
Br
'52-dibromoethane
The colour change in this reaction is from orange to colourless
This is used as a test for unsaturation to show the presence of a double bond"
c) Addition of hydrogen halides prodces a halogenoalkane
e#g# !"
2
#!"
2
$ "Br !"
3
!"
2
Br
bromoethane
+f this reaction is done with an unsymmetrical alkene5 two isomeric products may be
formed e#g#
!"
3
!"#!"
2
$ "Br !"
3
!"Br!"
3
2-bromopropane
and !"
3
!"#!"
2
$ "Br !"
3
!"
2
!"
2
Br

'-bromopropane
d) Addition of steam prodces an alcohol
e#g# !"
2
#!"
2
$ "
2
& !"
3
!"
2
&"
ethanol
9eeds a strong acid catalyst e#g# phosphoric acid5 H
&
:1
4
Temperature must be abo)e '**C so that H
2
1 is in the form of steam
e) 'echanism for Electrophilic Addition
The high electron density in the bond makes alkenes attracti)e to electrophiles
electron pair acceptors5 such as 4r
2
and H4r"
As the bromine molecule approaches the bond5 the electrons in the 4r-4r bond are
repelled# A dipole is induced in the bond with the 4r nearer the alkene being ;<
The 4r-4r bond undergoes heterolytic =ssion to produce a cation positi)e ion" and
an anion negati)e ion"5 4oth electrons from the bond go to the negati)e ion
Br
2
Br
$
$ (Br
)
The 4r
<
is the electrophile that accepts an electron pair from the bond to produce
an intermediate5 CH
2
4rCH
2
<
The intermediate is a carbocation it has a carbon with a positi)e charge"
+n organic mechanisms5 a curly arrow represents the mo)ement of a pair of
electrons
Curly arrows should start from a bond or lone pair and =nish at the atom where a
bond or lone pair is being formed
*) +olymerisation of Alkenes
Alkenes can %oin together to form addition polymers
>onomer = small molecule that can be polymerised
:olymer = long chain molecule formed by %oining many monomers together many
means se)eral thousand"
The bond breaks and forms single bonds that %oin the monomers together
a) E,amples
E-ation 2 repeat nits of polymer

.thene polyethene"
Chloroethene polychloroethene"
%) +rocessing of .aste polymers /e0g0 plastic %ottles)
'echanical Recycling ?aste polymers can be melted down and re-used following
separation into types :T6. etc"# Howe)er it is e7pensi)e to collect and sort waste
polymers
!om%stion for energy prodction ?aste polymers can be burnt as a fuel but
this may produce to7ic waste products see below"
1eedstock recycling ?aste polymers can be cracked and the products used to
make fuels and other polymers after separation"
d) 'inimising en2ironmental damage in polymer disposal
Chemists and chemical processes can minimise the en)ironmental damage caused by
disposing of polymers
!om%stion for energy prodction 4urning halogenated plastics5 such as :@C5
produces to7ic products like HCl# Howe)er5 the HCl can be remo)ed by gas
scrubbers which by dissol)e it in a spray of alkali
3e2eloping ne. polymers Addition polymers are not biodegradable they don8t
rot down"# Chemists ha)e de)eloped biodegradable and compostable polymers that
will rot down e#g# from isoprene methyl-'5&-butadiene"5 maiAe and starch