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Natures Nightmare: A study of the chemistry

of DDT and its effects on the environment.


Scott Zeglin
Synthesis of DDT DDT Biomagnification
Abstract
Dichlorodiphenyltrichloroethane, Cl OH The main reason DDT accumulates as
commonly known as DDT, is a powerful Cl
Cl O
H Cl
+ it moves up the food chain is because it is
OH Cl H
insecticide that combats the vectors of human Cl
OH Cl
- Chlorobenzene
hardly metabolized or excreted. This is
disease and crop pests. DDT was first used in H + O S O + H + O S O
because DDT is a lipophile, meaning that
OH Cl -HSO4-

World War II to combat infectious disease in


O Cl O
DDT binds to lipids, such as fat in animals.
humans, but its main use was as a pesticide Cl
This solubility in fat, coupled with the stability
until the EPA banned it in 1973. Problems Cl
provided by the anchoring of chlorobenzene
with DDT arose when it was discovered that groups at each end of the compound give a
the compound is stable and fat soluble, which highly stable compound almost incapable of
H
means that it accumulates in animal fat tissue Cl O
+ H
Cl O
H
Cl O
H being metabolized in the animal body.
Cl
and becomes more and more concentrated in Cl + H Cl H Cl H Cl H
the offspring of infected species. It is useful to Cl Cl Cl Cl
H

Conclusion
H+
+
understand why DDT is such a powerful
-H2O
insecticide, but also why its half-life in animals DDT poses a great risk to animals at
is so long (8 years). By analyzing the Cl Cl Cl Cl the top of the food chain. However, by
chemical make-up of this compound, understanding the chemistry behind why
improvements might be possible to make the DDT is such an effective insecticide allowed
compound non-soluble in fat or accumulating chemists to develop alternatives such as
Cl Cl
in animals, while still maintaining its lethal dieldrin and methoxychlor. These
effects towards pests. alternatives are typically more expensive
+ than DDT and are not typically as effective.
Introduction Cl
Cl
H
H Cl
Cl
H However, some of the better alternatives
are more environmentally friendly,
+
-H
Cl Cl
After World War II, DDT was the most
eliminating this nightmare from nature.
commonly used pesticide in the world, since it
seemed to eradicate all unwanted insects, and
Acknowledgements
Cl Cl
left all other organisms alone. DDT is an
organochlorine that undergoes biomagnification
as it accumulates through the food chain, which Kimball, John. (2003). [online], available HTTP:
means that higher concentrations of the chemical Mechanism http://users.rcn.com/jkimball.ma.ultranet/Biol
ogyP ages/I/Insecticides.html
will be found in animals at the top of the food
chain, but there is no evidence that DDT harms DDT can be synthesized from two starting products, Wikipedia, The Free Online Dictionary. (2000 or
humans in any way. The mechanism and Trichloroacetaldehyde and chlorobenzene. The reaction between later). [online], available HTTP:

synthesis of DDT was studied to understand why these two starting materials occurs primarily in the para position http://en.wikipedia.org/wiki/DDT

it is such a good insecticide, but what properties of chlorobenzene, yielding an intermediate alcohol, which in the Williamson, K.L. Macroscale and Microscale
allow it to be so harmful to non-target organisms. presence of acid, readily forms a second carbocation with another Organic Experiments, 2nd edition. 1994:
chlorobenzene. Houghton Mifflin, Boston.