Organic Chemistry

Alkanes and Alkenes

Boardworks Ltd 2001

Pure Hydrocarbons

Because the main use of hydrocarbons is as a

fuel there is no point in going to the effort to
separate them into individual hydrocarbons.
It is, however, possible to obtain pure
hydrocarbons by very careful distillation.
This section is about pure hydrocarbons.

Boardworks Ltd 2001

Carbon: Organic Chemistry

Carbon is an unusual atom in that it is able to

form very strong covalent bonds with other
carbon atoms.
When we then include its ability to also bond
with other elements we open up the possibility
of the highly diverse and complex molecules
(like DNA) that have led to the possibility of life.
Because of this, the chemistry of carbon
containing compounds is often called organic
chemistry.

Boardworks Ltd 2001

Alkanes

The simplest hydrocarbons form a series of

compounds known as alkanes.
These all consist of carbon and hydrogen only and
every carbon has four single covalent bonds.
Hydrocarbon

Formula

Methane

CH4

Ethane

C2H6

Propane

C3H8

Butane

C4H10

Structure

hydrogen
carbon

Boardworks Ltd 2001

Names of Alkanes

The names of the 4 simplest alkanes are methane,

ethane, propane and butane.
After that the names are systematic (like the words
used to describe geometric shapes.) E.g.

5 carbons = pentane
6 carbons = hexane
7 carbons = heptane
8 carbons = octane
9 carbons = nonane
10 carbons = decane
hydrogen

C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
pentane

carbon

Boardworks Ltd 2001

Homologous Series

Alkanes all have very similar structures.

They have a CH3 at each end of the molecule.
What differs is the number of CH2 groups
between the two ends.
These all consist of carbon and hydrogen only
and every carbon has four single covalent bonds.
It is possible to build up a series by simply adding
an extra CH2 group
This leads to a general formula of CnH2n+2
n= 1

n=2

n=3

n=4

hydrogen
carbon
Boardworks Ltd 2001

Activity

What will be the formula for alkanes

containing the following numbers of
carbons?
Number of carbons

Formula

12

C12H26

16

C16H34

31

C31H64

19

C19H40

Boardworks Ltd 2001

Formulae and Models of Alkanes

Although normal chemical formula - like C5H12 are used to describe alkanes they do not convey
which atom is joined to which other atom.
To get around this we often used displayed
formula to describe organic molecules.
Displayed formula show which 4 atoms each
carbon is bonded to but even these do not show
the actual 3D shapes. For that we use models.
H
methane, CH4

H
Boardworks Ltd 2001

Alkanes
H
H

methane, CH4

ethane, C2H6

propane, C3H8

Boardworks Ltd 2001

butane, C4H10

pentane, C5H12

Boardworks Ltd 2001

hexane, C6H14
H

Notice
the carbon chain
is not really
straight

and so on
Boardworks Ltd 2001

Isomerism
Alkanes of the same formula can have different
arrangements of atoms. Such different arrangments
are known as isomers.
Two isomers of C4H10 are shown
H H H
H C

H H H H
H C

H
H

H H H H
Isomers of butane

H
C

Boardworks Ltd 2001

Bonding in Alkanes: Methane, CH4

Alkanes contain atoms held together by single
covalent bonds.
In displayed formula we show these bonds as a
single line.
Each line is really a pair of shared electrons
H
H

H
H

H
H

Boardworks Ltd 2001

Alkanes: Ethane, C2H6

Ethane is the simplest alkane containing a CC single covalent bond.

Boardworks Ltd 2001

Activity
Complete the diagram below including its electrons.
Carbon electron

Hydrogen electron

Boardworks Ltd 2001

Combustion of Alkanes
Alkanes are not especially reactive but they do
have one very important reaction: combustion.
With an adequate supply of air they react to
form carbon dioxide and water. E.g.
Methane + oxygen water
CH4 + 2O2

2H2O

+ carbon dioxide
+

CO2

Boardworks Ltd 2001

Incomplete Combustion of Alkanes

In the absence of an adequate
supply of air alkanes may react
to form carbon monoxide and
water.
This is highly poisonous and
this is one reason why gas
boilers must be serviced
regularly.
Methane + oxygen water
2CH4 + 3O2

A carbon
monoxide
detector

+ carbon monoxide

4H2O

2CO
Boardworks Ltd 2001

Activity

Complete the equations below assuming ab

adequate supply of oxygen for complete
combustion. (These are quite tricky!)
1.1. 2C
7O22
2C22HH66 ++ 7O

4CO2 + 6H2O

2.
2.

C
C33H
H88

++

5O
5O22

3. 2C4H10 +
13O
3.
2C4H10 + 13O22

3CO2 + 4H2O
8CO2 + 10H2O

Boardworks Ltd 2001

Alkenes
When carbon forms compounds each carbon
atom always forms four bonds.
This does not, however, mean that each
carbon is joined to four other atoms.
It is possible to have bonds grouped into pairs.
These are called double bonds.
Alkenes contain carbon atoms joined by
double covalent bonds.
Single covalent bond

Double covalent bond

Boardworks Ltd 2001

Alkenes - homologous series

A series of alkanes exist differing only in the
number of CH2 groups.
The same is true for alkenes.
This leads to a homologous series with the
general formula Cn H2n
Alkenes
hydrogen
carbon

n= 1

n=2

none

n=3
=

n=4
=

Boardworks Ltd 2001

Activity

What will be the formula for alkenes

containing the following numbers of
carbons?
Number of carbons
11

Formula
C11H22

13

C13H26

32

C32H64

21

C21H42

Boardworks Ltd 2001

Ethene - formula
The simplest alkene is ethene.
It has the formula C2H4
The carbon atoms are joined together by a
double bond.
Its displayed formula may be drawn in slightly
different forms but should always clearly show
the double bond.
H

or

H
H

H
H

Boardworks Ltd 2001

Ethene electron structure

In all alkenes there
are two carbon
atoms that are joined
by two pairs of
electrons.
This is the double
bond.
H
H

Boardworks Ltd 2001

Activity

Displayed formula for propene and butene are

shown.
Draw a displayed structure for pentane.

H
H

H
C C

C
H

H
H

H H
H C
H
C H
C C H
H
H

H H
H C
H C H
H
C H
C C H
H
H

Boardworks Ltd 2001

Saturated or Unsaturated?
Saturated means full up.
Alkanes are saturated.
saturated
Every carbon atom has aleady used all four of
its bonds to join to four other atoms. No other
atoms can be added.
Alkenes are unsaturated.
unsaturated
They have a double bond that could instead
become two single bonds. This means that
other atoms can be added. It is not full up.
Boardworks Ltd 2001

 Alkenes are unsaturated and so extra atoms

can be added to alkene molecules.
This forms the basis of a test to distinguish
between alkanes and alkenes.
When bromine water is added to an alkane
nothing happens but when bromine is added
to an alkene the red colour of the bromine
disappears.
H

Bromine
loses this
red colour

Gas

H
H

Br2
red

Br Br
H C C H
H H

colourless

Boardworks Ltd 2001

Activity

Copy the Table and complete the empty boxes.

Number
of
carbons

Name

Alkane or
alkene

Formula

pentene

alkene

C5H10

octane

alkane

C8H18

butene

alkene

C4H8

10

decane

alkane

C10H22

Boardworks Ltd 2001

Industrial manufacture and uses

of Alkenes

Boardworks Ltd 2001

Alkenes Sources
Crude oil contains many large molecules.
If these are to be used as fuels or feedstock for
the chemical industry then they have to be broken
down (or cracked) into smaller molecules.
Small molecules
Big molecules
Medium
molecules

Fuel gas
Naphtha
Diesel

Petrol
Kerosine
Fuel Oil and bitumen

Boardworks Ltd 2001

Catalytic Cracking
Large hydrocarbons are broken into smaller
molecules using heat and a catalyst.
This process is known as catalytic cracking.
The small molecules produced are then separated
by distillation.
pressure

Big Molecules

Heat to
vaporise

Catalytic
cracker
Molecules
break up

Smaller molecules

Distillation
tower

Boardworks Ltd 2001

Catalytic Cracking
In the catalytic cracker long chain molecules are
split apart or cracked. An example of such a
reaction is:
H H H H H H H H
H C C C C C C C C H
H H H H H H H H

hexane

Heat
pressure

H H H H H H
H C C C C C C H
Used as H H H H H H

Octane

catalyst

H
H

C C

a fuel

C8H18 C6H14 + C2H4

H
H

ethene
Ethene
is used
to make
plastics
Boardworks Ltd 2001

Activity

Draw out displayed formulae of a pair of products

formed by cracking decane
H H H H H H H H H H
H C C C C C C C C C C H
H H H H H H H H H H
Heat
pressure

catalyst

H H H H H H H H
H C C C C C C C C H
H H H H H H H H
octane

decane

H
H

C C

H
H

ethene

Boardworks Ltd 2001

Poly(e)thene
One important reaction of alkenes involves the
joining together of alkene molecules.
H
H

C C

H H H H H H H H H H
H C C C C C C C C C C
H H H H H H H H H H

H
H

And
lots
more..

thousands

This is called addition polymerisation and is written as:

H
n

ethene

H
H

Pressure
high
temperature
catalyst

H H poly(e)thene
C C
H H n
Boardworks Ltd 2001

Polypropene
Ethene is only one alkene. Other unsaturated
molecules such as propene, vinyl chloride and
styrene can also be polymerised to produce a
range of plastics. E.g. propene

H
H

H
C C

C
H

H
H

H CH3
Poly(propene)
C C
H H
n

propene

Boardworks Ltd 2001

PTFE
Tetrafluoroethane is another alkene that is made
into an important plastic used to coat non-stick
pans: polytetrafluoroethane or PTFE.

F
n

C C

F
F

tetrafluoroethene

F F
C C
F F

Poly(tetrafluoroethane)
or PTFE

Boardworks Ltd 2001

Activity

Fill in the products that will be obtained from

vinyl chloride

H
H

Cl
C C

Vinyl chloride

H Cl
C C
H H

pvc

Boardworks Ltd 2001

Some uses of plastics

Poly(e)thene

Polypropene

Polystyrene

Shopping bags

Milk crates

packing

Bottles

Rope

insulation

Buckets

Carpet fibres

Ball pens

Washing up
bowls

Boardworks Ltd 2001

Across

Down

3) separate
substances
with different
boiling points

1) Contain a
double bond

7) saturated
hydrocarbon

2) a series of
molecules
differing by a CH2

8) joining of
many small
molecules

4) breaking up a
large molecules

9) full up:
unable to add
more atoms

5) the different
substances
collected from
distillation
6) used to test for
unsaturated
molecules.

Boardworks Ltd 2001

Answers
Across

Down

3) separate substances with

different boiling points
DISTILLATION

1)
Contain a double bond
ALKENE

7) saturated hydrocarbon
ALKANE

2) a series of molecules differing by a

CH2
HOMOLOGOUS

8) joining of many small molecules

POLYMERISE

4) breaking up a large molecules

CRACKING

9) full up: unable to add more atoms

SATURATED

5) the different substances collected

from distillation
FRACTIONS
6) used to test for unsaturated
molecules.
BROMINE

Boardworks Ltd 2001

Which of these is an alkane?

A. C6H14
B. C4H8
C. C12H24
D. C102H204

Boardworks Ltd 2001

Which of these is a true statement about

alkenes?
A. They turn bromine water from colourless to
red
B. They contain a double bond
C. The smallest alkene has 1 carbon atom
D. They have names that end in ane.

Boardworks Ltd 2001

Which of these is a true statement about

cracking?
A. it is the separation of molecules into
fractions of different sizes.
B. it is carried out at low temperatures
C. it uses a catalyst.
D. It produces polymers

Boardworks Ltd 2001

Which of these is a true statement about

polymerisation?
A.it is the joining together of many small
molecules.
B. it is the thermal decomposition of plastics
C.it is carried out using saturated molecules
D.it is a multiplication reaction

Boardworks Ltd 2001

Which of these is an addition polymer?

A.
B.
C.
D.

styrene
ethene
p.v.c.
propane

Boardworks Ltd 2001

How might you test to see if polystyrene still

contained some unsaturated monomer (styrene)?
A.
B.
C.
D.

Crush it up and burn it.

Crush it up and add it to bromine water
Crush it up and dissolve it in petrol
Crush it up and add hydrochloric acid

Boardworks Ltd 2001