USES OF HALOGENOALKANES

This page looks at some of the uses of halogenoalkanes

(haloalkanes or alkyl halides) as required by UK A level
syllabuses.

CFCs and their replacements

What are CFCs?

CFCs are chlorofluorocarbons - compounds containing carbon

with chlorine and fluorine atoms attached. Two common CFCs
are:

CFC-11 CCl3F

CFC-12 CCl2F2

How to work out the formula from the CFC

number: You add 90 to the CFC number to give a new
number. For example, CFC-11 generates the number
101 (11+90)

The first digit of the new number tells you how many
carbon atoms there are. The second number tells you
the number of hydrogens, and the third the number of
fluorines. You calculate the number of chlorines from
the formula Cl = 2(C+1)-H-F.

Uses of CFCs

CFCs are non-flammable and not very toxic. They therefore had
a large number of uses.

They were used as refrigerants, propellants for aerosols, for

generating foamed plastics like expanded polystyrene or
polyurethane foam, and as solvents for dry cleaning and for
general degreasing purposes.

Unfortunately, CFCs are largely responsible for destroying the

ozone layer. In the high atmosphere, the carbon-chlorine bonds
break to give chlorine free radicals. It is these radicals which
destroy ozone. CFCs are now being replaced by less
environmentally harmful compounds.

Note: You will find the mechanism for the depletion of

ozone by the chlorine radicals produced from CFCs on
the introduction to catalysis page in the physical
chemistry section of this site.

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CFCs can also cause global warming. One molecule of CFC-11,

for example, has a global warming potential about 5000 times
greater than a molecule of carbon dioxide.

On the other hand, there is far more carbon dioxide in the

atmosphere than CFCs, so global warming isn't the major
problem associated with them.

Replacements for CFCs

These are still mainly halogenoalkanes, although simple alkanes

such as butane can be used for some applications (for example,
as aerosol propellants).

Hydrochlorofluorocarbons, HCFCs

These are carbon compounds which contain hydrogen as well

as halogen atoms. For example:

HCFC-22 CHClF2

The formula can be worked out from the number in the name in
exactly the same way as for CFCs.

These have a shorter life in the atmosphere than CFCs, and

much of them is destroyed in the low atmosphere and so doesn't
reach the ozone layer. HCFC-22 has only about one-twentieth of
the effect on the ozone layer as a typical CFC.

Hydrofluorocarbons, HFCs

These are compounds containing only hydrogen and fluorine

attached to carbon. For example:

HFC-134a CH2F-CF3

Because these HCFCs don't contain any chlorine, they have

zero effect on the ozone layer. HFC-134a is now widely used in
refrigerants, for blowing foamed plastics and as a propellant in
aerosols.

Hydrocarbons

Again, these have no effect on the ozone layer, but they do have
a down-side. They are highly flammable and are involved in
environmental problems such as the formation of photochemical
smog.

Other uses of organic halogeno compounds

In making plastics

Strictly speaking, the compounds we are talking about here are

halogenoalkenes, not halogenoalkanes, but one of the UK A
level syllabuses includes them in this section.

Chloroethene, CH2=CHCl, is used to make poly(chloroethene) -

usually known as PVC.

Tetrafluoroethene, CF2=CF2, is used to make

poly(tetrafluoroethene) - PTFE.

Note: These are both discussed in detail on the page

about polymerisation of alkenes.
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Lab uses of halogenoalkanes

If you refer to the halogenoalkanes menu (see below), you will

find that they react with lots of things leading to a wide range of
different organic products.

Halogenoalkanes are therefore useful in the lab as

intermediates in making other organic chemicals.

2.8 EXERCISE 2 – reactions of haloalkanes

1. a) Draw the structure of a chlorofluorocarbon and write an equation to show

how it can release chlorine radicals in the presence of ultra-violet light.

b) Write equations to show how chlorine radicals can catalyse the destruction of ozone.

2. a) Explain why haloalkanes can react with nucleophiles.

 b) Write an equation and give the mechanism for the following reactions:

i) bromoethane with aqueous sodium hydroxide

ii) 2-chloropropane with potassium cyanide

iii) 1-iodobutane with ammonia

3. State two types of reaction that could take place when 1-chlorobutane reacts with potassium
hydroxide. Give the mechanism for each reaction and state the role of the hydroxide ion in each
case. Suggest conditions which would favour each type of reaction.

4. Suggest, giving reasons, which of chloroethane, bromoethane and iodoethane will react fastest
with sodium hydroxide.

5. State the possible products that could be formed when the following haloalkanes undergo
elimination. If more than one product is formed, identify them both and explain how each is
formed.

a) 1-bromobutane

b) 2-bromobutane

c) 1-bromomethylpropane

d) 2-bromomethylpropane