Organic Chemistry- Alkenes

Students should be able to:

11.2 Alkenes
(a) describe the alkenes as an homologous series of unsaturated hydrocarbons with the general formula C nH2n

(b) *draw the structures of branched and unbranched alkenes, C2 to C4, and name the unbranched alkenes, ethene to butene

(c) describe the manufacture of alkenes and hydrogen by cracking hydrocarbons and recognise that cracking is essential
to match the demand for fractions containing smaller molecules from the refinery process

(d) describe the difference between saturated and unsaturated hydrocarbons from their molecular structures and by using
aqueous bromine

(e) describe the properties of alkenes in terms of combustion, polymerisation and the addition reactions with bromine, steam
and hydrogen

(f) state the meaning of polyunsaturated when applied to food products

(g) describe the manufacture of margarine by the addition of hydrogen to unsaturated vegetables oils to form a solid product

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Alkenes
Structure of Alkenes

n Name Molecular Displayed Formula Structural formula Empirical Boiling Physical

Formula (Full Structural Formula) (Condensed formula) Formula Point (ºC) State at
r.t.p
2 Ethene C2H4 CH2=CH2 or CH2CH2 CH2 -104

3 Propene C3H6 CH2=CHCH3 or CH2 -48

CH2CHCH3 gas

4 Butene C4H8 CH2=CHCH2CH3 or CH2 -6

CH2CHCH2CH3

Summary
(a) Characteristics of Alkenes
1. Alkenes have a general formula of CnH2n.
2. Each member of the alkene homologous series differs from the next by a –CH2 unit.

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(b) Alkenes are unsaturated because they contain C=C bonds.
(c) This general formula is for alkenes with only one C=C (carbon-carbon double bond).
Alkenes having more than one C=C bonds do not conform to the general formula CnH2n. Those with 2 C=C have the general formula CnH2n-2, and
those with 3 C=C have the general formula CnH2n-4 etc.

(d) Note that the first member of the alkene homologous series is ethene. Methene, with 1 carbon atom, does not exist!

(e) Alkenes have the same empirical formula of CH2.

Draw the “dot and cross” diagram for propene.

Isomerism in Alkenes
Alkenes also form isomers.
Isomers are compounds with the same molecular formula but different structural formula.
The number of isomers increases as the number of carbon atoms in a molecule increase.

n Molecular Possible Structural Formulae From other homologous series

Formula (Alkene Homologous Series )
2 C2H4 -

3 C3H6

1 1

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4 C4H8

3 2
5 C5H10

5 5
Conclusions : Isomers may come from different homologous series.

Only those under the same series show similar chemical properties.

However, all isomers show different physical properties to different extent.

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Preparation of Alkenes
 Petroleum (crude oil) is mainly a mixture of alkanes.
 Many of these alkanes are long chain molecules (with a lot of carbon atoms).
 However, there is a high demand for short chain alkanes, for example, petrol (C5 –C10), for fuel
in motor vehicles.
 That is, the high demand for short chain hydrocarbon is not matched by its supply.
 In the industry, this problem is solved by catalytic cracking.

Catalytic Cracking
 Cracking is a process involving the breaking of long chain hydrocarbon molecules into shorter
ones.
 This process is essential to match the demand for fractions containing smaller molecules from
the refinery process (fractional distillation of crude oil).
 A catalyst, eg aluminium oxide (Al2O3) or silicon dioxide (SiO2) may be used to speed up the
cracking process at high temperature (about 5000C).

 Other products, such as small alkenes and hydrogen are also produced.

 Examples of possible reactions:

eg 1. C12H26  C4H10 + C8H16

eg 2. C18H38  C6H14 + 6C2H4 or

C18H38  C8H16 + C10H20 + H2

Importance of Catalytic Cracking

1. Cracking is used to produce short chain alkanes.
The amount of petrol fraction obtained from the fractional distillation of petroleum is an
insufficient supply for all the cars in the world. Therefore, the short alkanes produced from
cracking can be used to supplement the supply of petrol and meet its demand.

2. Cracking is used to produce short chain alkenes.

Short-chain alkenes like ethene and propene are used as raw material to manufacture ethanol
and plastics like poly(ethene).

3. Cracking is used to produce hydrogen.

Hydrogen is an important raw material for the manufacture of ammonia in the Haber Process
(which can be used to manufacture nitrogenous fertilisers) and the manufacture of margarine,
and also as fuel for rockets and hydrogen-oxygen fuel cells.

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Chemical Reactions of Alkenes
 Alkenes are generally more reactive than alkanes because they contain C=C bonds.
 They are called unsaturated hydrocarbons.
 Thus, alkenes will undergo two different kinds of reactions – combustion and addition reactions
(which includes polymerisation).

1. Combustion
Alkenes also burn in air when ignited by a spark or flame. When alkenes undergo complete
combustion in excess air (oxygen), carbon dioxide and water are the only products formed.

An example when ethene reacts with excess air (oxygen) in a complete combustion reaction:

ethene + oxygen  carbon dioxide + water

C2H4 + 3O2  2CO2 + 2H2O

When there is insufficient oxygen, incomplete combustion takes place. As a result, carbon
monoxide and soot (unburnt carbon) are formed.
Alkenes also burn with a more smoky flame compared to alkanes because alkenes have a higher
percentage by mass of carbon, so more oxygen is needed for complete combustion per unit mass.

Compound Ethane Ethene

Molecular Formula C2H6 C2H4
% by mass of carbon (2x12)/(2x12+6) x (2x12)/(2x12+4) x
100% = 80% 100% = 85.7%

2. Addition Reactions
 As alkenes are unsaturated compounds, they will undergo addition reactions instead of
substitution reactions.
 Definition: An addition reaction is one in which reactant molecules combine to form a single
molecular product.
 In an addition reaction, carbon-carbon double bonds become single bonds.
 Hence,an unsaturated organic compound becomes a saturated organic compound.

a) Addition of Aqueous Bromine

CnH2n + Br2  CnH2nBr2

Aqueous bromine, or bromine water, is used. (Do not say bromine solution. Why?)
When an alkene is added to bromine water, the reddish-brown bromine water turns
colourless spontaneously, ie bromine has been decolourised spontaneously.
This is because the alkene has undergone an addition reaction with bromine.

Conditions : Bromine dissolved in water

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eg 1. Reaction of ethene with aqueous bromine: Ethene + bromine  1,2-dibromoethane

Equation (Molecular formulae): C2H4 + Br2  C2H4Br2

Equation (Structural Formulae): CH2=CH2 + Br2  CH2BrCH2Br

Equation (Full structural formulae):

eg 2. Reaction of propene with aqueous bromine: Propene + bromine  1,2-dibromopropane

Equation (Molecular formulae): C3H6 + Br2  C3H6Br2

Equation (Structural Formulae): CH2=CHCH3 + Br2  CH2BrCHBrCH3

Equation (Full structural formulae):

eg 3. Reaction of but-2-ene with aqueous bromine: but-2-ene + bromine  2,3-dibromobutane

Equation (Molecular formulae): C4H8 + Br2  C4H8Br2

Equation (Structural Formulae): CH3CH=CHCH3 + Br2  CH3CHBrCHBrCH3

Equation (Full structural formulae):

eg 4. Formation of 1,2-dibromobutane: but-1-ene + bromine  1,2-dibromobutane

Equation (Molecular formulae): C4H8 + Br2  C4H8Br2

Equation (Structural Formulae): CH2=CHCH2CH3 + Br2  CH2BrCHBrCH2CH3

Equation (Full structural formulae):

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Conclusion for addition of bromine: The two bromine atoms are added to the two carbon atoms
holding the double bond. Other carbon atoms are not affected.

Application of the reaction: bromine water can be used to distinguish between saturated and
unsaturated compounds, because unsaturated compounds will decolourise bromine water
spontaneously whereas saturated compounds will not react with bromine water (i.e. bromine water
remains reddish-brown). Addition of bromine is used as a chemical test for the presence of
unsaturated hydrocarbons.

bromine
water

bromine water

Figure 6. Testing for the presence of alkenes

Additional Practice:
1) How many moles of aqueous bromine are needed to completely react with 1 mole of the
following compound? Draw the full structure of the final product.

2) Which of the following saturated compounds are obtained from hydrocarbons through a)
substitution reaction ONLY? b) addition reaction ONLY? c) either substitution or
addition reaction?

A B C D

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b) Addition of steam
CnH2n (g) + H2O (g)  CnH2n+1OH (l)
Conditions : 3500C, 65 atm, H3PO4 (phosphoric (V) acid) as catalyst (Ea very high)
This process is used in the industries to manufacture alcohols, especially ethanol.

eg 1. Reaction of ethene with steam: Ethene + steam  ethanol

Equation (Molecular formulae): C2H4 + H2O  C2H5OH

Equation (Structural Formulae): CH2=CH2 + H2O  CH3CH2OH

Equation (Full structural formulae):

eg 2. Reaction of propene with steam: Propene + steam  propan-1-ol and propan-2-ol

Equation (Molecular formulae): C3H6 + H2O  C3H7OH

Equation (Structural Formulae): CH2=CHCH3 + H2O  CH2OHCH2CH3 and CH3CHOHCH3

Equation (Full structural formulae):

eg 3 Reaction of but-1-ene with steam: But-1-ene + steam  butan-1-ol and butan-2-ol

Equation (Molecular formulae): C4H8 + H2O  C4H9OH

Equation (Structural Formulae): CH2=CHCH2CH3 + H2O  CH2OHCH2CH2CH3 and

CH3CHOHCH2CH3

Equation (Full structural formulae):

eg 4. Reaction of but-2-ene with steam: But-2-ene + steam  butan-2-ol

Equation (Molecular formulae): C4H8 + H2O  C4H9OH

Equation (Structural Formulae): CH3CH=CHCH3 + H2O  CH3CHOHCH2CH3

Equation (Full structural formulae):

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Conclusion for addition of steam:
When the C=C bond is broken, one carbon atom accepts the H atom and the other carbon atom
accepts the –OH group. In many cases different alcohols could be obtained.

c) Addition of hydrogen
 In the presence of a catalyst like nickel and with heat, alkenes can react with hydrogen to form
alkanes.
 Addition of hydrogen (commonly known as hydrogenation) is used to make margarine from
vegetable oil.

CnH2n + H2  CnH2n+2

Conditions : Ni as catalyst, heat

For example, when ethene reacts with hydrogen, ethane is formed:
Ethene + hydrogen  ethane

Equation (Molecular formula): C2H4 + H2  C2H6

Equation (Full structural formula): CH2=CH2 + H2  CH3CH3

Application of addition of hydrogen :

 Manufacture of margarine
 Vegetable oils are polyunsaturated. They are large organic molecules that contain many
carbon-carbon double bonds.
 Margarine is manufactured by reacting vegetable oil with hydrogen in the presence of nickel as
a catalyst. Some of the carbon-carbon double bonds in vegetable oils undergo an addition
reaction to form single bonds. Margarine contains less double bonds compared to vegetable oils.

Margarine is a solid and vegetable oil is a liquid at room temperature. This is because margarine has
a higher melting point than vegetable oil. The margarine molecules have a greater relative molecular
mass and size than vegetable oil. The margarine molecules contain lesser double bonds, therefore the
molecules will have a more linear shape (Refer to Figure 7). This molecular structure allows many
molecules to be rather closely "stacked" together. As a result, stronger intermolecular forces of
attraction result in relatively high melting points.

On the other hand, vegetable oil molecules contain more double bonds, resulting in more "bends" in
the molecule. These molecules do not "stack" very well. The intermolecular forces of attraction are
much weaker than saturated molecules. As a result, the melting points are much lower for
unsaturated fats.

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Figure 7. Structure of saturated fats and unsaturated fats

d) Addition Polymerisation
(teacher may choose to teach the process here and give some examples, but details of uses of
the polymers would be covered under Macromolecules)

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Comparison between alkanes and alkenes
Alkanes (saturated) Alkenes (unsaturated)
Type of compound Contains only carbon and hydrogen
General formula CnH2n+2 CnH2n

Molecular Structure Contains only C-C bonds Contains C=C bonds

Reactivity Less reactive More reactive

Type of reaction Complete combustion to produce carbon dioxide and water

Alkenes burn with a more smoky flame (due to higher % of carbon)

Substitution reactions with Addition reactions (to form a

halogens (ultraviolet light single molecular product)
needed) a) Adding of aqueous bromine to
form bromoalkanes (can be used
1 or more hydrogen atoms in to test for unsaturation)
alkanes are replaced by atoms b) Adding of steam to form
from other groups, for example alcohols (sometimes, 2 isomeric
Group VII elements alcohols could be formed)
c) Adding of hydrogen to form
Products include the alkanes
chloroalkane/bromoalkane (if d) Addition polymerization to
Group VII elements are used for form polymers
substitution) and HCl/HBr

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