10.

8 Polyhalogen Carbon compounds containing more than one halogen atom are usually
referred to as polyhalogen compounds. Many of these compounds are
Compounds useful in industry and agriculture. Some polyhalogen compounds are
described in this section.
10.8.1 Dichloro- Dichloromethane is widely used as a solvent as a paint remover, as a
methane propellant in aerosols, and as a process solvent in the manufacture of
(Methylene drugs. It is also used as a metal cleaning and finishing solvent. Methylene
chloride) chloride harms the human central nervous system. Exposure to lower
levels of methylene chloride in air can lead to slightly impaired hearing
and vision. Higher levels of methylene chloride in air cause dizziness,
nausea, tingling and numbness in the fingers and toes. In humans, direct
skin contact with methylene chloride causes intense burning and mild
redness of the skin. Direct contact with the eyes can burn the cornea.
10.8.2 Trichloro- Chemically, chloroform is employed as a solvent for fats, alkaloids,
methane iodine and other substances. The major use of chloroform today is in
(Chloroform) the production of the freon refrigerant R-22. It was once used as a
general anaesthetic in surgery but has been replaced by less toxic,
safer anaesthetics, such as ether. As might be expected from its use as
an anaesthetic, inhaling chloroform vapours depresses the central
nervous system. Breathing about 900 parts of chloroform per million
parts of air (900 parts per million) for a short time can cause dizziness,
fatigue, and headache. Chronic chloroform exposure may cause damage
to the liver (where chloroform is metabolised to phosgene) and to the
kidneys, and some people develop sores when the skin is immersed in
chloroform. Chloroform is slowly oxidised by air in the presence of
light to an extremely poisonous gas, carbonyl chloride, also known as
phosgene. It is therefore stored in closed dark coloured bottles
completely filled so that air is kept out.

10.8.3 Triiodo- It was used earlier as an antiseptic but the antiseptic properties are
methane due to the liberation of free iodine and not due to iodoform itself. Due
(Iodoform) to its objectionable smell, it has been replaced by other formulations
containing iodine.

10.8.4 Tetrachlo- It is produced in large quantities for use in the manufacture of

romethane refrigerants and propellants for aerosol cans. It is also used as
(Carbon feedstock in the synthesis of chlorofluorocarbons and other chemicals,
tetrachloride) pharmaceutical manufacturing, and general solvent use. Until the mid
1960s, it was also widely used as a cleaning fluid, both in industry,
as a degreasing agent, and in the home, as a spot remover and as fire
extinguisher. There is some evidence that exposure to carbon
tetrachloride causes liver cancer in humans. The most common effects
are dizziness, light headedness, nausea and vomiting, which can cause
permanent damage to nerve cells. In severe cases, these effects can lead
rapidly to stupor, coma, unconsciousness or death. Exposure to CCl4
can make the heart beat irregularly or stop. The chemical may irritate
the eyes on contact. When carbon tetrachloride is released into the air,
it rises to the atmosphere and depletes the ozone layer. Depletion of the
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 ozone layer is believed to increase human exposure to ultraviolet rays,
leading to increased skin cancer, eye diseases and disorders, and
possible disruption of the immune system.
10.8.5 Freons The chlorofluorocarbon compounds of methane and ethane are collectively
known as freons. They are extremely stable, unreactive, non-toxic, non-
corrosive and easily liquefiable gases. Freon 12 (CCl2F2) is one of the
most common freons in industrial use. It is manufactured from
tetrachloromethane by Swarts reaction. These are usually produced
for aerosol propellants, refrigeration and air conditioning purposes. By
1974, total freon production in the world was about 2 billion pounds
annually. Most freon, even that used in refrigeration, eventually makes
its way into the atmosphere where it diffuses unchanged into the
stratosphere. In stratosphere, freon is able to initiate radical chain
reactions that can upset the natural ozone balance (Unit 14, Class XI).
10.8.6 p,p’-Dichlo- DDT, the first chlorinated organic insecticides, was originally prepared
rodiphenyl- in 1873, but it was not until 1939 that Paul Muller of Geigy
trichloro- Pharmaceuticals in Switzerland discovered the effectiveness of DDT as
ethane(DDT) an insecticide. Paul Muller was awarded the Nobel Prize in Medicine
and Physiology in 1948 for this discovery. The use of DDT increased
enormously on a worldwide basis after World War II, primarily because
of its effectiveness against the mosquito that spreads malaria and lice
that carry typhus. However, problems related to extensive use of DDT
began to appear in the late 1940s. Many species of insects developed
resistance to DDT, and it was also discovered to have a high toxicity
towards fish. The chemical stability of DDT and its fat solubility
compounded the problem. DDT is not metabolised very rapidly by
animals; instead, it is deposited and stored in the fatty tissues. If
ingestion continues at a steady rate, DDT builds up within the animal
over time. The use of DDT was banned in the United States in 1973,
although it is still in use in some other parts of the world.

Summary
Alkyl/ Aryl halides may be classified as mono, di, or polyhalogen (tri-, tetra-, etc.)
compounds depending on whether they contain one, two or more halogen atoms in
their structures. Since halogen atoms are more electronegative than carbon, the carbon-
halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive
charge, and the halogen atom bears a partial negative charge.
Alkyl halides are prepared by the free radical halogenation of alkanes, addition
of halogen acids to alkenes, replacement of –OH group of alcohols with halogens using

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