HSC CHEMISTRY LESSON PLAN 26

4.1.7 Identify the origins of chlorofluorocarbons (CFCs) and halons in the atmosphere

Chlorofluorocarbons are compounds which contain only chlorine, fluorine and carbon in their
structure. They are very inert and have a low boiling point. They began to be used extensively in the
1980s, when they replaced ammonia in refrigeration, were used in air conditioners, were used as
solvents to clean electrical circuits and as blowing agents in the production of plastics and foam. E.g.
CCl3F, CCl2F2 . CFCs gradually (3-5 years) make their way up to the stratosphere because they are
inert and do not react in the troposphere.

 Freon-11 [CCl3F] was used as aerosol propellant, and for blowing plastic foams
 Freon-12 [CCl2F2] was used as a refrigerant
 Freon-113 [C2Cl3F3] was used as a solvent
Halon’s are CFC’s which also contain bromine and were used (and still are) in fire extinguishers to
combat electrical fires and to protect electrical circuits in computers.
 Halon 1011, bromochloromethane [CH2BrCl] was used extensively in fire extinguishers for
electrical fires
 Halon use has been drastically reduced because bromine atoms are more effective than
chlorine atoms in reactions that lead to depletion of the ozone layer

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4.1.8 Identify and name examples of isomers (excluding geometrical and optical) of haloalkanes up
to eight carbon atoms

In naming haloalkanes

1. The halogen functional groups are named using prefixes placed in front of the name of the
alkane: F: fluoro- Cl: chloro- Br: bromo- I: iodo-
2. Select the longest unbranched hydrocarbon chain in the haloalkane molecule. Count the
number of carbons in this chain. This number will decide the stem name of the alkane.
3. Number the chain from the end that produces the lowest set of locants (numbered positions)
for all the functional groups including any alkyl functional groups that may also be present along
the chain. (Note: The lowest set of locants is the set which, when compared term by term with
other locant sets, each cited in order of increasing value, has the lowest term at the first point
of difference.)
4. In naming the haloalkanes, the functional groups are named alphabetically using the locants to
designate positions (disregard prefixes such as di-, tri- etc. in this alphabetical ordering).
 5. If the previous rules lead to more than one possible name, then the correct name is the one in
which the lowest locant is assigned to the functional group cited first as a prefix. The most
electronegative halogen is given priority in numbering: F>Cl>Br>I.

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4.1.9 Discuss the problems associated with the use of CFCs and assess the effectiveness of steps
taken to alleviate these problems

Problems with CFC use and emissions

1. CFC’s are unreactive (inert), and insoluble in water. As a result they do not break down in the
lower atmosphere, rather over a period of 3-5 years they reach the atmosphere
2. High level of UV radiation at this level is able to break the C-Cl bond in CFC’s, releasing chlorine
free radical which destroys O3 in a chain process, without being used themselves

CCl3F (g) + UV light CCl2F3· (g) + Cl· (g)

Cl· (g) + O3 ClO· (g) + O2 (g)

ClO· (g) + O· (g) O2 (g) + Cl· (g)

The only way the Cl· can stop reacting is if it reacts with CH4 or NO2:

Cl· (g) + CH4 CH3· (g) + HCl (g)

ClO· (g) + NO2 (g) ClONO2 (g)

A chain reaction occurs and thousands of ozone molecules can be destroyed by one chlorine atom
(from the CFC), significantly decreasing ozone concentration. Less O3 increases harmful radiation
entering Earth and reaching the surface.

a. This interrupts DNA and cell division causing skin cancer. In Punta Arenas in Chile
(one of the southern most cities in the world), skin cancers are up 66% between
1987 and 2000
b. This also interferes with bacterial processes. E.g. cyanobacteria convert nitrogen in
air to nitrates in the soil for crops such as rice and wheat to use. Without this crop
productivity would fall.
 c. It also interferes with plankton growth which forms the basis of the food chain in
many marine ecosystems, disrupting marine ecology.
d. It also increases cataracts in eyes
e. Also causes more brittleness in synthetic polymer structures
3. Furthermore, CFCs are not easily removed from the atmosphere as they are insoluble in water
and therefore do not get washed out of the atmosphere by rain. CFCs can last up to 150 years in
the atmosphere.

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Assess the steps taken to alleviate the problems

There have been many steps taken to alleviate the problems of CFC emissions since their mass
production in the 1970’s. CFC’s are extremely inert, insoluble in water and so were able to be used in
refrigeration, production of foam, plastics, aerosols and cleaning of electrical circuits. However due
to their very inert properties, they do not break down in the lower atmosphere, rather, they rise to
the ozone layer where high intensity UV rays break the C-Cl bond in them. E.g. CCl3F breaks down
according to:

CCl3F (g) + UV light CCl2F3· (g) + Cl· (g)

Which then reacts with O3: Cl· (g) + O3 ClO· (g) + O2 (g)

And the ClO· reacts with atmospheric O·: ClO· (g) + O· (g) O2 (g) + Cl· (g)

Which reforms the Cl· which can continue to destroy O3 in a chain reactions. The only way for this to
stop is when Cl· reacts with atmospheric methane or when ClO· reacts with NO2:

Cl· (g) + CH4 CH3· (g) + HCl (g)

ClO· (g) + NO2 (g) ClONO2 (g)

As a result the ozone layer is depleted, which allows more UV rays into the Earth’s surface than
usual. This has caused a severe increase in skin cancer rates up from 66% since 1987-2000. It has
also increases cataracts in eyes, suppresses the immune response and is able to cause more
brittleness in synthetic polymer structures. It also interferes with plankton growth which forms the
basis of the food chain in many marine ecosystems, disrupting marine ecology. This also interferes
with bacterial processes. E.g. cyanobacteria convert nitrogen in air to nitrates in the soil for crops
such as rice and wheat to use. Without this crop productivity would fall.
Many steps have been taken in order to alleviate problems caused by CFC’s. The 2985 Vienna
conference was aimed to investigate the effect of CFC’s on the ozone layer. The 1987 Montreal
Protocol on substances that cause ozone depletions aimed to set out guidelines for the phasing out
of halons and cause CFC’s by 1996. The 1997 Kyoto Convention set out a final date of 2010 for
developing countries and developed countries to phase out halons and CFC’s. USA and 12 other
European countries aimed to stop CFC production by 2000.

Ne sunscreens have been introduced with higher SPF’s to protect people from increased UV light.
More UV resistant sunglasses have also been developed to protect eyes.

New education campaigns in schools and in public such as “slip, slop, slap” aim to protect people
from UV rays. New materials such as HCFC’s and HFC’s have been developed which have a
significantly lower ODP than CFC’s, with HFC’s having a 0 ODP as they do not contain chlorine. These
alternatives have gradually been moved into CFC roles. E.g. HCFC -123 is able to be used in plastic
production

There have been many advantages to these steps. The ozone layer has begun to patch up due to the
less CFC’s being emitted. Without these, O3 is replenished naturally:

O·(g) + O2 (g) O3 (g)

The newer sunscreens have protected people against the problem of excessive UV light onto the
Earth’s surface. The newer products to replace CFC’s, especially HFC’s have a severely lowered ODP.
Replenishment of the ozone layer was reported in an Australian study in September 2002, in which it
stated ozone should begin to replenish in 5 years with the process being complete in 2050.

However there have also been many disadvantages. HFC’s and HCFC’s are not very potent
greenhouse gases, much more potent than CO2. They are also not as efficient to use in place of
CFC’s. Many of the developing countries have problem implementing the changes as they are more
expensive. As a result a black market has been established in these developing countries which have
lowered the effectiveness of these steps.

It can be seen that overall these steps have been effective in alleviating CFC problems seen by the
replenishment of the ozone layer and continuing of the process. However further economic aid must
continue to develop countries to introduce these changes and better replacement chemicals must
be developed.

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O3 levels began to be monitored in 1957 mainly using UV spectrophotometers. Since then there has
been a marked decrease in O3 concentrations in the atmosphere’s upper regions. In 1985 there was
30% ODP and in 1993 35% ODP over Antarctica measured. It was around this time that ozone
depleting CFC’s stopped being produced, however Cl· have a large lifetime and in 2000 ozone
depletion of 10% to 40% was observed as the ozone-hole reached 3X the area of the USA and
covered an area of approximately 11 million square miles. However in 2004 ozone depletion was
large, but the duration of the ozone hole was the shortest observed since 1988. It could be said that
ozone concentrations have started to increase again, however due to continued presence of the Cl·,
it will not be complete until 2050

O3 depletion occurs mainly over Antarctica, as the planets wind currents, carry CFC emissions
towards the poles, mainly Antarctica where a polar vortex forms not allowing Antarctic stratospheric
gases to mix with those around then. Polar stratospheric clouds also exist over Antarctica which are
clouds formed at altitudes of 15-35km and temperatures below -80OC. These clouds provide surfaces
to catalyse certain reactions during the Antarctic winter:

HCl (g) + ClHNO3 (g) Cl2 (g) + HNO3 (g)

When winter in Antarctica, the Cl· also combine to form Cl2 gas. However when the first UV rays hit
these molecules, the split to form Cl·:

Cl2 (g) Cl· (g) + Cl· (g)

This causes large O3 depletion in the Antarctic, and the formation of the ozone hole, which is a very
low concentration of O3 in one area of the Antarctic stratosphere. The hole gradually shrinks as the
vortex around the South Pole breaks and allows Antarctic stratospheric air to mix with surrounding
air, bringing O3 concentration back to ‘normal’ levels by summer.

Monitoring Ozone Depletion

Many techniques are utilised to monitor stratospheric ozone levels. UV spectrophotometers were
one of the first to be utilised. When UV light enters the upper atmosphere, it is absorbed by ozone at
certain wavelengths. When it reaches the Earth’s surface, the UV is detected and the wavelengths
absorbed by O3 can be compared with those that aren’t. As this absorption is proportional to
concentration we are able to monitor atmospheric ozone concentrations.

Total Ozone Mapping Spectrometer (TOMS) is a device attached to satellites such as the Nimbus 7
and accurately detects O3 concentrations at a number of areas at the same time, to develop a map
of ozone depletion. UV spectrophotometers are also often added to helium balloons and released
into the atmosphere. They use the same ground based principle as the ground based instruments,
but can give ozone concentrations relative to altitude in the sky.
Lasers known as LIDARS are also fired in electric pulses into the atmosphere. They also use radar
technology in that light is reflected of the O3 and can be detected as it returns. The intensity and
time taken of the light to return can determine concentration and altitude of ozone.

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4.1.11 present information from secondary sources to write the equations to show the reactions
involving CFCs and ozone to demonstrate the removal of ozone from the atmosphere

CCl3F (g) + UV light CCl2F3· (g) + Cl· (g)

Cl· (g) + O3 ClO· (g) + O2 (g)

ClO· (g) + O· (g) O2 (g) + Cl· (g)

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4.1.12 Gather, process and present information from secondary sources including simulations,
molecular model kits or pictorial representations to model isomers of haloalkanes

Use this space to write down the method used in class

Many replacements for CFC’s have been developed in an effort to aid the replenishment of O3 in the
stratosphere. Mainly HCFC’s and HFC’s have begun to be introduced. CFC’s are extremely inert
materials that do not dissolve in water, allowing them to be used for refrigeration, air conditioning,
blowing agents in plastics and foam, cleaning electric circuits and in aerosol cans. However they
were so inert and unreactive, they did not break down in the lower atmosphere, rather they reach
the stratosphere over a period of 3-5 years. Here high intensity UV radiation breaks the C-Cl bond in
CFC’s. E.g. CCl3F breaks down according to:

CCl3F (g) + UV light CCl2F3· (g) + Cl· (g)

Which then reacts with O3: Cl· (g) + O3 ClO· (g) + O2 (g)

And the ClO· reacts with atmospheric O·: ClO· (g) + O· (g) O2 (g) + Cl· (g)

Which reforms the Cl· which can continue to destroy O3 in a chain reactions. The only way for this to
stop is when Cl· reacts with atmospheric methane or when ClO· reacts with NO2:

Cl· (g) + CH4 CH3· (g) + HCl (g)

ClO· (g) + NO2 (g) ClONO2 (g)

As a result the ozone layer is depleted, which allows more UV rays into the Earth’s surface than
usual. This has caused a severe increase in skin cancer rates up from 66% since 1987-2000. It has
also increases cataracts in eyes, suppresses the immune response and is able to cause more
brittleness in synthetic polymer structures. It also interferes with plankton growth which forms the
basis of the food chain in many marine ecosystems, disrupting marine ecology. This also interferes
with bacterial processes. E.g. cyanobacteria convert nitrogen in air to nitrates in the soil for crops
such as rice and wheat to use. Without this crop productivity would fall.
As a result HCFC’s were introduced as temporary replacements to CFC’s. They are compounds
containing hydrogen, chlorine,
fluorine and carbon. Due to their C-H
bond in their structure, the HCFC’s
can react with OH free radicals in the
lower troposphere. HCFC’s such as
HCFC-123 (CF3CHCl2) are used in
plastic foam production and
decomposes down to CO2, water and
hydrogen halides in a very slow
reaction. Due to the very slow nature
of this reaction, Cl· still reach the
atmosphere but their ODP is 10%
that of similar CFC’s. E.g. The ODP of
HCFC-123 is 0.02, yet the ODP of CFC-
11 (most widely used CFC) is 1.
Although their ODP is significantly less, HCFCs are only temporary replacements for CFC’s and will be
phased out by 2040.

HCF’s were the next main alternative chemicals to be developed. They contain only hydrogen,
fluorine and carbon. They contain no Cl in their structure and so have a 0 ODP. They are similar to
CFC’s as they are non toxic and odourless as well as being relatively inert (but more reactive than
CFC’s). This means that HFC’s can be used in similar areas as CFC’s. E.g. In Australia HFC-134A has
been extensively to replace CFC’s in air conditioning and refrigeration units HFC’s can be seen as
longer term solutions.

HFC’s significantly lower OD as compared to CFC’s. HFC’s also have 0 ODP and so are very beneficial.
HCFC’s and HFC’s also have similar properties to CFC’s and so can be used in similar areas.

However they are more expensive, less efficient to use in many areas and are greenhouse gases.
(HFC-134A has a greenhouse potency 3400 times that of CO2).

The criteria for this evaluation is cost of implementation, environmental benefits and ability to be
used in similar areas as CFC’s due to similar properties.

The implementation of HCFC’s as temporary replacements and HFC’s as longer term replacements
has been overall effective due to their decreased ODP and similar properties to CFC’s. However they
are both greenhouse gases and so they impact on the enhanced greenhouse effect must be
considered. As a result research in the development of CFC replacements must continue,

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1. Describe the impact of CFC’s on the ozone layer using at least THREE equations (4 Marks)
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2. Evaluate the effectiveness of alternatives to CFC’s (6 Marks)
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3. Assess the effectiveness of steps taken to alleviate issues to do with the use of CFCs (6
Marks)
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4. Name the following haloalkanes
5. Describe at least THREE techniques to collect information regarding ozone concentrations
in the atmosphere (3 Marks)
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