Alkenes 2023

1 of 34 © Boardworks Ltd 2009

What are alkenes?
The alkenes are a homologous series of hydrocarbons
with the general formula CnH2n and names ending –ene.
Alkenes contain a carbon – carbon double bond and so are

unsaturated.
No. of Molecular Name

carbon atoms formula
2 C2H4 ethene
3 C3H6 propene
4 C4H8 butene
5 C5H10 pentene
6 C6H12 hexene

Naming alkenes
Alkenes with four or more carbon atoms display positional
isomerism because the carbon–carbon double bond may
appear between different carbon atoms.
If there are two or more possible positions for the double

bond, a number is used before the –ene to indicate the first
carbon involved.
but-1-ene but-2-ene

Structure of alkenes

Bonding in alkenes

Isomerism in alkenes
Rotation around the double bond in alkenes is restricted
by the presence of the  bond. This leads to E–Z
stereoisomerism in some alkenes.
E-pent-2-ene Z-pent-2-ene
The two E-Z stereoisomers have the same structure; the

only difference between them is the arrangement of the
atoms in space.

Rotation around the C=C bond in alkenes
Molecules can rotate freely around single C-C covalent
bonds, but not around C=C double bonds.
This leads to type of stereoisomerism called cis–trans

isomerism, in which isomers differ in the arrangement of
the groups attached to the carbons in the double bonds.
is not the
same as
These isomers cannot be superimposed on each other

because the arrangement of the methyl groups is different.

Cis–trans isomerism
If an alkyl group or atom other than hydrogen is attached
to each carbon then the isomers can be named either
cis (‘on the same side’) or trans (‘on the opposite side’).
cis-but-2-ene trans-but-2-ene
cis-1,2-dichloroethene trans-1,2-dichloroethene
Limitations of cis–trans isomerism
In more complex organic compounds, in which multiple
hydrogens have been substituted by different groups,
isomers cannot be defined using the cis–trans notation.
For example, is it possible to identify which of these

halogenoalkanes is the cis isomer and which is the
trans isomer?
Instead, a different system is used for these type of

molecules: E–Z notation.

E–Z isomerism
The E–Z notation is used to identify stereoisomers that
cannot be called cis or trans.
Isomers are identified as either E or Z depending on what

‘priority’ is given to the groups attached to the carbon
atoms in the double bond. The priority of these groups is
determined by a complex series of rules.
⚫ E represents the German word ‘entgegen’, and

corresponds to trans isomers. The highest priority
groups are on the opposite side of the double bond.
⚫ Z represents the German word ‘zusammen’, and

corresponds to cis isomers. The highest priority
groups are on the same side of the double bond.

E–Z isomerism
Because there are four different atoms attached to the C=C, the idea of two
identical groups being in a cis- or trans- arrangement cannot work
This is where E-Z system is useful.

E–Z isomerism

How to recognize the possibility of
geometrical isomerism
This molecule cannot show

geometrical isomerism since identical
atoms are bonded on each carbon of
the C=C bond.

atoms (H,H and Cl,Cl) are bonded on
same carbon of the C=C bond.

How to recognize the possibility of
geometrical isomerism

atoms (H,H) are bonded on same
carbon of the C=C bond.
This molecule exhibits geometrical

isomerism since identical
atoms (H,H) are bonded on each
carbon of the C=C bond.
Structure of alkenes summary

Addition reactions of Alkene
Why do addition reactions occur?
• C=C bond in an alkene is made up of a sigma bond and a pi
bond. Sigma bond is stronger than pi bond
• This means a double bond is stronger than a single bond, but
it is not twice as strong
• Most reactions of alkenes involve the double bond becoming a
single bond
• In these reactions, the sigma bond remains unchanged, but pi
bond electrons are used to form new bonds with an attacking
molecule.
• This reaction forms a product that is saturated

1. Halogenation
• This is a typical addition reaction of alkenes
C2H4 + Br2 → C2H4Br2
• This reaction is used as a chemical test for the presence of
C=C in a compound
• The bromine is normally used as aqueous bromine
• Positive result: the solution goes from brown to colorless

1. Halogenation

1. Halogenation
• The products of these reactions are dihalogenoalkanes.

Double bonds and electrophiles
The double bond of an alkene is an area of high electron
density, and therefore an area of high negative charge.
The negative charge of the double bond may be attacked

by electron-deficient species, which will accept a lone pair
of electrons.
These species have either a full positive charge or slight

positive charge on one or more of their atoms. They are
called electrophiles, meaning ‘electron loving’.
Alkenes undergo addition reactions when attacked by

electrophiles. This is called electrophilic addition.

Electrophilic addition mechanism: step 1
In the first stage of electrophilic addition,
the positive charge on the electrophile is
attracted to the electron density in the
double bond.
δ+ δ-
As the electrophile approaches the
double bond, electrons in the A–B
→
bond are repelled towards B.
The pi bond breaks, and A bonds to the

carbon, forming a carbocation – an ion
with a positively-charge carbon atom.
The two electrons in the A–B bond
move to B forming a B- ion.

Electrophilic addition mechanism: step 2
In the second stage of electrophilic
addition, the B- ion acts as a nucleophile
and attacks the carbocation.
→
The lone pair of electrons on the B- ion
are attracted towards the positively-
charged carbon in the carbocation,
causing B to bond to it.
Because both electrons in the bond that joins B- to the

carbocation ion come from B-, the bond is a co-ordinate bond.

1. Halogenation Mechanism
Step 1
Step 2
• Attacking bromine molecule does not have a polar bond

• However, as it approaches the C=C bond, the electrons in pi bond repel
electrons in the Br-Br bond and induce the molecule to become polar.
More on the bromine water test
A simple equation for the bromine water test with ethene is:
CH2=CH2 + Br2 + H2O → CH2BrCH2Br + H2O
However, because water is present in such a large

amount, a water molecule (which has a lone pair) adds to
one of the carbon atoms, followed by the loss of a H+ ion.
CH2=CH2 + Br2 + H2O → CH2BrCH2OH + HBr
The major product of the test is not 1,2-dibromoethane

(CH2BrCH2Br) but 2-bromoethan-1-ol (CH2BrCH2OH).

2. Addition of hydrogen halides
• This is addition of a hydrogen halide(often hydrogen bromide
or hydrogen chloride) to form a halogenoalkane(more
specifically, a bromoalkane or chloroalkane

2. Addition of hydrogen halides Mechanism
Step 1
In this step 2 ions are
formed. The positive ion
has its charge on a
carbon atom, so it is
known as a carbocation.
Step 2
The two oppositely charged
ions attract each other and
react to form a new covalent
bond as one of the lone
pairs of electrons forms a
covalent bond with the
carbon atom in the
carbocation.
Asymmetric alkenes
• With symmetrical molecules H-Br produces only one product
• However, with asymmetric alkenes two products are formed.
• This is because the
atoms in the attacking
molecule can be added
in two different places
HBr
Unequal amounts of
each product are
formed due to the
relative stabilities of
the carbocation
intermediates. minor product: major product:
1-bromopropane 2-bromopropane
Asymmetric alkenes Structure of carbocations
A chain of carbon atoms can be represented by R when
drawing organic structures. This is an alkyl group (general
formula CnH2n+1).
⚫ Primary (1°) carbocations have
one alkyl group attached to the
positively-charged carbon.
⚫ Secondary (2°) carbocations

have two alkyl groups attached
to the positively-charged carbon.
⚫ Tertiary (3°) carbocations have

three alkyl groups attached to
the positively-charged carbon.

Asymmetric alkenes Stability of carbocations
The stability of carbocations increases as the number of alkyl
groups on the positively-charged carbon atom increases.
primary secondary tertiary
increasing stability
The stability increases because alkyl groups contain a greater

electron density than hydrogen atoms.
Akyl groups are electron releasing groups, so when there are
more of them, the charge on the carbocation is spread more

Asymmetric alkenes
In this example, the product

formed is 2-bromopropane
because that product is HBr
formed from a secondary
carbo cation which is more
stable than the primary
carbocation formed during
formation of 1-bromopropane minor product: major product:
1-bromopropane 2-bromopropane

Asymmetric alkenes
Summary
Reactions involving asymmetrical molecules are complex, so
here is a quick summary.
• Electrophilic addition reactions proceed via carbocations
• Carbocations can be primary, secondary or tertiary
• The stability of a carbocation is greatest for tertiary
carbocations and least for primary carbocations
• Carbocations are more stable when there are more electron
releasing alkyl groups attached to the carbon with the
positive charge
• The major product is formed from the more stable carbocation
Addition reactions of Alkenes
3. Hydrogenation
Hydrogen can be added to the carbon–carbon double bond
using a nickel catalyst in a process called hydrogenation.
C 2 H 4 + H2 → C 2 H 6
This reaction forms alkanes from akenes

This reaction is done using heat and a nickel catalyst
Reagent: H2 gas
conditions: Heat + Ni catalyst
Product : Alkane
3. Hydration
• Hydration means adding water, but you should consider it as
adding H and OH to the two atoms in a C=C double bond.
• This reaction is usually done by heating the alkene with steam
and passing the mixture over a catalyst of phosphoric acid
Reagent: H2O (g) / steam

conditions: Heat + H3PO4
Product : Alcohol
4. Oxidation to diols
• Diol contains 2 OH groups.
• Oxidising agent is potassium manganate(vii)in acid
• The potassium manganate(vii) provides an oxygen
atom(oxidation) and the water in the solution provides another
oxygen atom and 2 hydrogen atoms so there is addition of 2
OH groups across the double bond.
Reagent: Potassium permanganate (vii)

conditions: Acid
Product : diol
ethane-1,2-diol
• The symbol [O] represents the oxygen supplied by oxidising
agent
• You do not need to show the potassium permanganate in the
equation or know how it supplies the oxygen for the oxidation
• Potassium permanganate changes from purple to colourless
in acid medium
• In alkaline medium, the colour change
is from purple to green

ethane-1,2-diol
• Under acidic conditions, the manganate(VII) ions

are reduced to manganese(II) ions(colourless).
• Under alkaline conditions, the manganate(VII)

ions are first reduced to green manganate(VI)

Polymerisation reactions
Alkenes can undergo addition reactions with themselves
to form a long chain polymer molecule. This reaction is
addition polymerization.

Naming Polymers
❑ When alkene molecules are used in polymerisation,
they are often referred to as monomers.
❑ The standard way to name a polymer is by writing
‘poly’, followed by the name of the monomer in
brackets. Example: poly(ethene)

Equations for polymerisation reactions
❑ The usual way to do this is to use the letter ‘n’ to
represent the number of monomer molecules reacting,
then to show the repeat unit of the polymer inside a
bracket (curved or square)
❑ The letter n is shown as a subscript after the bracket,
and there are covalent bonds shown passing through
the brackets to indicate that there is another repeat unit
joined on to each side

Here is the equation showing the formation of poly(ethene)
Here is the equation showing the formation of poly(propene)

This equation shows the formation of poly(chloroethene),
better know as PVC
This equation shows the formation of poly(phenylethene)

better known as polystyrene

Identifying the Monomer
• If you are given the repeat unit of a polymer, or a section of
the polymer that contains several repeat units, you can work
out the structure of the corresponding monomer.
• You need to identify the part of the structure that is repeated
• This will be two carbon atoms in the chain and the four carbon
atoms or groups joined to them
• The monomer structure is all of these atoms, but with a
double bond between the two carbon atoms.
• This is part of the structure of poly(methyl

methacrylate) better known as Perspex
Identifying the Monomer
• This is part of the structure of poly(methyl methacrylate) better
known as Perspex
• There are no brackets and no subscripts n, because this

shows part of the structure and not just the repeat unit
• You can see that on alternate carbon atoms in the chain, there
are two hydrogen atoms, one methyl group and one CHOOCH3
group. The monomer structure is:

More about LDPE
LDPE is a soft, flexible and stretchy plastic, with a melting
point of about 120 °C. It is used to make:
⚫ plastic bags
⚫ squeezable bottles, and

general purpose
containers and trays
⚫ other items that need to

be soft and flexible, such
as tubing.
LDPE has the recycling symbol ‘4’.

More about HDPE
HDPE is a tough and flexible plastic, with a melting point of
about 130 °C. It is used to make:
⚫ containers such as milk and

detergent bottles
⚫ rigid items such as folding

tables, chairs and pipes.
HDPE has the recycling symbol ‘2’.

More about polypropene
Polypropene is a tough and flexible plastic, with a melting
point of about 160 °C. It is used to make:
⚫ ropes, carpets, rugs and other
textiles
⚫ medical, laboratory and
kitchen items that need to
withstand temperatures in
autoclaves and dishwashers
⚫ certain bottles, buckets, containers
and other items such as bottle
tops and moulded fittings.
Polypropene has the recycling symbol ‘5’.

Dealing with polymer waste
• Polymers are relatively cheap to make when they are mass
produced and many people see them as disposable.
• Many years ago, ‘disposable’ meant that after use, the only
thing to do was to throw the object away, perhaps in a bin,
to be forgotten and taken away by the refuse collecting
service.

Solutions to polymer waste
• Not to use polymers unnecessarily. In some countries, the use
of single use plastic bags by supermarkets has been banned
• Recycling. Example: poly(ethylene terephthalate),PET, is
widely used in plastic bottles, and this polymer is now recycled
on a large scale to make carpets
• Incineration (burning the polymers) is widely used. Although
this method gets rid of the polymer waste, unfortunately it
leads to the formation of carbon dioxide and also some toxic
gases.
• Biodegradable polymers are considered by many scientists to
be worth developing

Incineration
• Incineration is burning of polymers. Although this method
gets rid of the polymer waste, unfortunately it leads to the
formation of carbon dioxide and also some toxic gases.
• An incinerator takes in polymer waste and converts it into
heat energy that can be used to heat homes and factories,
or used to generate electricity.
• Apart from hydrogen and carbon, there other elements like
chlorine and small amounts of toxic heavy metals from the
pigments used to colour plastic. These pollutants are
difficult to remove from wate gases released into the
atmosphere.
Biodegradable polymers
• Biodegradable polymers or biopolymers are broken down
by microbes in the environment.
• Biopolymers are used on a small scale in medicine (for
sutures(stitches)and in drug delivery)
• However, there are some disadvantages:
• They are often made from plant material, so there is the
same issue to consider as with biofuels, that is, land is
needed to grow the plants
• They are designed to break down in the environment, so
when they do, the hydrogen and carbon atoms they contain
cannot be directly used.

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1 of 34 © Boardworks Ltd 2009

2 of 34 © Boardworks Ltd 2009

Alkenes contain a carbon – carbon double bond and so are

No. of Molecular Name

3 of 34 © Boardworks Ltd 2009

If there are two or more possible positions for the double

4 of 34 © Boardworks Ltd 2009

5 of 34 © Boardworks Ltd 2009

6 of 34 © Boardworks Ltd 2009

The two E-Z stereoisomers have the same structure; the

7 of 34 © Boardworks Ltd 2009

This leads to type of stereoisomerism called cis–trans

These isomers cannot be superimposed on each other

8 of 34 © Boardworks Ltd 2009

For example, is it possible to identify which of these

Instead, a different system is used for these type of

10 of 34 © Boardworks Ltd 2009

Isomers are identified as either E or Z depending on what

⚫ E represents the German word ‘entgegen’, and

⚫ Z represents the German word ‘zusammen’, and

11 of 34 © Boardworks Ltd 2009

12 of 34 © Boardworks Ltd 2009

13 of 34 © Boardworks Ltd 2009

This molecule cannot show

This molecule cannot show

14 of 34 © Boardworks Ltd 2009

This molecule cannot show

This molecule exhibits geometrical

16 of 34 © Boardworks Ltd 2009

18 of 34 © Boardworks Ltd 2009

19 of 34 © Boardworks Ltd 2009

20 of 34 © Boardworks Ltd 2009

• The products of these reactions are dihalogenoalkanes.

21 of 34 © Boardworks Ltd 2009

The negative charge of the double bond may be attacked

These species have either a full positive charge or slight

Alkenes undergo addition reactions when attacked by

22 of 34 © Boardworks Ltd 2009

The pi bond breaks, and A bonds to the

23 of 34 © Boardworks Ltd 2009

Because both electrons in the bond that joins B- to the

24 of 34 © Boardworks Ltd 2009

• Attacking bromine molecule does not have a polar bond

CH2=CH2 + Br2 + H2O → CH2BrCH2Br + H2O

However, because water is present in such a large

CH2=CH2 + Br2 + H2O → CH2BrCH2OH + HBr

The major product of the test is not 1,2-dibromoethane

26 of 34 © Boardworks Ltd 2009

27 of 34 © Boardworks Ltd 2009

⚫ Secondary (2°) carbocations

⚫ Tertiary (3°) carbocations have

30 of 34 © Boardworks Ltd 2009

primary secondary tertiary

The stability increases because alkyl groups contain a greater

31 of 34 © Boardworks Ltd 2009

In this example, the product

32 of 34 © Boardworks Ltd 2009

This reaction forms alkanes from akenes

Reagent: H2O (g) / steam

Reagent: Potassium permanganate (vii)

37 of 34 © Boardworks Ltd 2009

• Under acidic conditions, the manganate(VII) ions

• Under alkaline conditions, the manganate(VII)