Organic Chemistry

622

16

Reactions of

Substituted Benzenes

Chlorobenzene meta-Bromobenzoic acid

ortho-Chloronitrobenzene

para-Iodobenzenesulfonic acid

CHCHNHCCHCl 2

CH 2 OH

O 2 N

chloramphenicol

an antibiotic that is particularly

effective against typhoid fever

OH O

PEYOTE CULTS

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

southwestern United States, primarily among Native Americans. The followers of this religion

believe that the cactus is divinely endowed to shape each person’s life. Currently, the only people

in the United States who are legally permitted to use peyote are members of the Native Ameri-

can Church—and then only in their religious rites.

CH 2 CH 2 NH 2

CH 3 O OCH 3

OCH 3

mescaline

active agent of

the peyote cactus

M

any substituted

benzenes are found

in nature. A few that

have physiological activity are adrenaline, melanin, ephedrine, chloramphenicol, and

mescaline.

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

CHCH 2 NHCH 3

OH

HO

adrenaline

epinephrine

OH

CHCHNHCH 3

CH 3

ephedrine

a bronchodilator

OH