BRUI16-622_668r3 27-03-2003 3:54 PM Page 622

Reactions of
16 Substituted Benzenes

Chlorobenzene meta-Bromobenzoic acid

ortho-Chloronitrobenzene

M
any substituted
benzenes are found para-Iodobenzenesulfonic acid
in nature. A few that
have physiological activity are adrenaline, melanin, ephedrine, chloramphenicol, and
mescaline.
OH O OH OH
CHCHNHCCHCl2 CHCH2NHCH3 CHCHNHCH3
CH2OH CH3
O2N HO
OH
chloramphenicol adrenaline ephedrine
an antibiotic that is particularly epinephrine a bronchodilator
effective against typhoid fever

Many physiologically active substituted benzenes are not found in nature, but exist
because chemists have synthesized them. The now-banned diet drug fen-phen is
a mixture of two synthetic substituted benzenes: fenfluramine and phentermine. Agent
Orange, a defoliant widely used in the 1960s during the Vietnam War, is also a mix-
ture of two synthetic substituted benzenes: 2,4-D and 2,4,5-T. The compound TCDD

PEYOTE CULTS CH2CH2NH2

For several centuries, a peyote cult existed among the Aztecs in Mexico, which
later spread to many Native North American tribes. By 1880, a religion that com-
bined Christian beliefs with the Native American use of the peyote cactus had developed in CH3O OCH3
southwestern United States, primarily among Native Americans. The followers of this religion OCH3
believe that the cactus is divinely endowed to shape each persons life. Currently, the only people mescaline
in the United States who are legally permitted to use peyote are members of the Native Ameri- active agent of
can Churchand then only in their religious rites. the peyote cactus

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