Learning Objectives
• Recognize aromatic
compounds from structural
formulas.
• Name aromatic compounds
given formulas.
• Write formulas for aromatic
compounds given their
names.
Introduction
• In early 19th century, the term aromatic was used
to describe some fragrant compounds
coal distillate cherries, peaches and almonds Tolu balsam
• Currently, the term aromatic is used to refer to the
class of compounds related structurally to benzene
steroidal hormone analgesic tranquilizer
Properties of Aromatic
Compounds
• Benzene are mostly nonpolar
and slightly miscible in
water but miscible in alcohol
and other organic solvent
• Clear, colorless having a
strong yet fair odor
• Their carbon to hydrogen
ratio is high therefore, they
are characterized by sooty
yellow flame.
• Its vapors are narcotic and toxic and
excessive inhilation may cause hepatitis
• Extremely flammable the vapor is
poisonous and harmful
• It is harmful when contact with skina
1. Sources of Aromatic Hydrocarbons
• There are two main sources of simple
aromatic hydrocarbons:
i. coal
ii. petroleum
i. High temperature distillation of coal tar
– Coal is a mixture of benzene-like rings joined together.
Under high temperature, it produces coal tar which,
upon fractional distillation, yields:
Hoffmann isolated benzene from
coal-tar.
Benzopyrene
It is estimated that more than 1,000 t of benzopyrene are emitted into
the air over the United States each year. Only a few milligrams of
benzopyrene per kilogram of body weight are required to induce cancer
in experimental animals.
https://www.youtube.com/watch?v=lvUCYtQNDX0
ii. Heating petroleum at high temperature under
high pressure over a catalyst
– Petroleum consists mainly of alkanes which, at high
temperature under pressure over a catalyst, convert
into aromatic compounds.
2. Naming Aromatic Compounds
• Aromatic compounds are named according to the
system devised by the International Union of Pure and
Applied Chemistry (IUPAC).
• Aromatic compounds have many common names
that have been accepted by IUPAC:
• Toluene = methylbenzene
• Phenol = hydroxybenzene
• Aniline = aminobenzene
A phenyl group consists of a benzene ring with one
of its hydrogens removed.
Monosubstituted benzenes
• Monosubstituted benzenes, like hydrocarbons, are
systematically named with –benzene as the parent
name
C6H5Br C6H5NO2 C6H5CH2CH2CH3
Arenes
• Arenes are alkyl-substituted benzenes
– If # Csubstituent < or = 6, then the arene is named as
an alkyl-substituted benzene
– If # Csubstituent > 6, then the arene is named as a
phenyl-substituted alkane
Aryl groups
• “Phenyl” refers to C6H5
– It is used when a benzene ring is a substituent
– “Ph” or “f” can also be in place of “C6H5 ”
• “Benzyl” refers to “C6H5CH2 ”
Disubstituted benzenes
• Relative positions on a disubstituted benzene ring:
– ortho- (o) on adjacent carbons (1,2 disubstituted)
– meta- (m) separated by one carbon (1,3 disubstituted)
– para- (p) separated by two carbons (1,4 disubstituted)
• The ortho- (o), meta- (m), and para- (p) nomenclature
is useful to describe reaction patterns
Example: “Reaction of toluene with Br2 occurs at the para
position”
Multisubstituted benzenes
• Multisubstituted benzenes (more than two substituents)
are named as follows:
– Choose the sequence when the substituents have the lowest
possible number
– List substituents alphabetically with hyphenated numbers
– Use common names, such as “toluene”, as parent name (as in
TNT)
– Use common names, such as “toluene”, as parent name
▪ The principal substituent is assumed to be on C1
▪ See Table 15.1
Practice Problem: Tell whether the following compounds are
ortho-, meta-, or para-disubstituted
(a) Meta (b) Para (c) Ortho
Practice Problem: Give IUPAC names for the following
compounds
(a) m-Bromochlorobenzene (b) (3-Methylbutyl)benzene
(c) p-Bromoaniline (d) 2,5-Dichlorotoluene
(e) 1-Ethyl-2,4-dinitrobenzene (f) 1,2,3,5-Tetramethylbenzene
Practice Problem: Draw structures corresponding to the
following IUPAC names:
a) p-Bromochlorobenzene
b) p-Bromotoluene
c) m-Chloroaniline
d) 1-Chloro-3,5-dimethylbenzene
Biologically Important
Compounds with Benzene
Rings
• Plants can synthesize the benzene ring from carbon
dioxide, water, and inorganic materials. Animals cannot
synthesize it, but they are dependent on certain aromatic
compounds for survival and therefore must obtain them
from food. Phenylalanine, tyrosine, and tryptophan
(essential amino acids) and vitamins K, B2 (riboflavin),
and B9 (folic acid) all contain the benzene ring. Many
important drugs, a few of which are shown in Table 13.8.2
, also feature a benzene ring
Chapter 15
