1

Aromaticity

Aims
By the end of this chapter, you should understand:
• The structure of benzene
• The concept of aromaticity and its application to various
organic systems
• The fundamentals of naming derivatives of benzene

1.1 Introduction
The classification of organic compounds is based on the structure of the
molecules. Aliphatic compounds have open-chain structures such as
hexane (1) and can contain single (C–C), double (C=C) and triple (C≡C) 1 2
bonds. In alicyclic molecules, the carbon atoms form a cyclic structure,
as in cyclohexane (2) and cyclohexene (3).
Aromatic compounds are unsaturated cyclic molecules that possess
3 4
additional stability as a result of the arrangement of π-electrons
associated with the unsaturation of the ring system. This book will
The term “aromatic”
concentrate on the chemistry of benzene (4) and its derivatives and acknowledges the fact that many
related polynuclear hydrocarbons. Aromatic compounds are also known fragrant compounds contain
as arenes; they can be carbocyclic, indicating that the ring skeleton con- benzene rings, whilst the term
“aliphatic” is derived from the
tains only carbon atoms, or heterocyclic, with at least one atom other Greek word for fat or oil.
than carbon in the ring. These heteroatoms are typically N, O or S. Benzene was isolated in 1825 by
Heterocyclic compounds, which can be aromatic or alicyclic, are covered Faraday from whale oil and in
in another book in this series. 1845 by Hofmann from coal tar.
Benzene is a colourless,
Initially, we will look at what distinguishes aromatic compounds from flammable liquid, with a boiling
other cyclic molecules and how chemists’ understanding of aromaticity point of 80 °C. It is carcinogenic.
has developed up to the present day.

1
2 Aromatic Chemistry

1.2 Structure of Benzene

Based on elemental composition and relative molecular mass determi-
nations, the formula of benzene was found to be C6H6. The saturated
hydrocarbon hexane has the molecular formula C6H14 and therefore it
was concluded that benzene was unsaturated. Kekulé in 1865 proposed
the cyclic structure 4 for benzene in which the carbon atoms were joined
by alternate single and double bonds. Certain reactions of benzene,
such as the catalytic hydrogenation to cyclohexane, which involves the
addition of six hydrogen atoms, confirmed that benzene was a ring
compound and that it contained three double bonds. However, since
benzene did not undergo addition reactions with HCl and HBr, it was
concluded that these double bonds were different from those in ethene
Note that these structures were
and other unsaturated aliphatic compounds.
proposed before the electron had In 1867, Dewar proposed several possible structures for benzene, one
been discovered and before the of which was 5. However, in 1874, Ladenburg proved experimentally
idea of the covalent bond had
that all the hydrogen atoms of benzene were equivalent and suggested
been developed.
the prismatic structure 6.
Kekulé’s proposed structure 4 looks more in keeping with our current
knowledge of benzene, although it does not explain how the double
bonds differ from the aliphatic type. Furthermore, although the two
5 6 structures 7 and 8 can be drawn for a 1,2-disubstituted benzene, only
R R one such compound exists. Kekulé proposed that the equivalent struc-
tures 7 and 8 oscillated between each other, averaging out the single and
R R
double bonds so that the compounds were indistinguishable.

7 8 1.3 Stability of the Benzene Ring

Kekulé’s proposals gained wide acceptance and were supported by the
experimental work of Baeyer in the late 19th century, but these ideas did
not explain the unusual stability of benzene. This is typified by its chem-
ical reactions, which are almost exclusively substitution rather than the
expected addition. Throughout this book there will be many examples
of this property. In addition, physical properties such as enthalpies
of hydrogenation and combustion are significantly lower than would be
expected for the cyclohexatriene structure of Kekulé. The enthalpy
of hydrogenation (∆H) of the double bond in cyclohexene is –120 kJ
mol–1 and that of cyclohexa-1,3-diene with two double bonds is almost
twice that at –232 kJ mol–1. Cyclohexatriene, if it existed, would be
expected to have an enthalpy of hydrogenation of three times the value
of cyclohexene, a ∆H of approximately –360 kJ mol–1. However, the value
for benzene is less exothermic than this comparison suggests, being only
–209 kJ mol–1. Thus benzene is 151 kJ mol–1 more stable than cyclo-
hexatriene (Figure 1.1). This is known as the resonance energy of ben-
 Aromaticity 3

+ 3H2

predicted aromatic
energy for stabilization
cyclohexatriene
151 kJ mol–1
+ 2H2
360 kJ mol–1
benzene + 3H2

+ H2

Energy 232 kJ mol–1

209 kJ mol–1

120 kJ mol–1

cyclohexane

zene or its aromatic stabilization. This stabilizing feature dominates the Figure 1.1 Hydrogenation of
chemistry of benzene and its derivatives. cyclohexene, cyclohexadiene and
benzene

1.3.1 Valence Bond Theory of Aromaticity

X-ray crystallographic analysis indicated that benzene is a planar, regular
hexagon in which all the carbon–carbon bond lengths are 139 pm, inter-
mediate between the single C–C bond in ethane (154 pm) and the C=C
bond in ethene (134 pm), and therefore all have some double bond
character. Thus the representation of benzene by one Kekulé structure A single bond has a bond order
is unsatisfactory. The picture of benzene according to valence bond the- of 1 and a double bond a bond
ory is a resonance hybrid of the two Kekulé or canonical forms 4 and order of 2.
9, conventionally shown as in Figure 1.2, and so each carbon–carbon
bond apparently has a bond order of 1.5. Figure 1.2

4 9 10 5 11 12
Kekulé structures Dewar structures
4 Aromatic Chemistry

A double-headed arrow, ↔, is
Although the canonical forms for benzene are imaginary and do not
used to connect resonance exist, the structure of benzene will be represented by one of the Kekulé
structures. structures throughout this book. This is common practice. A circle with-
in a hexagon as in 10, symbolic of the π-cloud, is sometimes used to rep-
It is emphasized that the circle
inside a ring represents resent benzene.
exclusively six π-electrons.

The three Dewar structures 5, 11 1.3.2 Molecular Orbital Theory of Benzene

and 12 (Dewar benzene) are also
considered to contribute to the The current understanding of the structure of benzene is based on molec-
resonance hybrid (according to ular orbital (MO) theory. The six carbon atoms of benzene are sp2
valence bond theory,
approximately 20% in total) and
hybridized. The three sp2 hybrid orbitals of each carbon atom, which are
to the extra stability. Dewar arranged at angles of 120°, overlap with those of two other carbon atoms
benzene has now been prepared. and with the s orbital of a hydrogen atom to form the planar σ-bonded
It is a bent, non-planar molecule
skeleton of the benzene ring. The p orbital associated with each carbon
and is not aromatic. It gradually
reverts to benzene at room contains one electron and is perpendicular to the plane of the ring.
temperature. The Ladenburg MO theory tells us that the six parallel p atomic orbitals are com-
structure, prismane (6), is an bined together to form six MOs, three of which are bonding orbitals and
explosive liquid. Dewar benzene
and prismane are valence three anti-bonding. Figure 1.3 shows the relative energy levels of these
isomers of benzene. MOs. The six π-electrons occupy the three bonding orbitals, all of lower
energy than the uncombined p orbitals; the higher energy anti-bonding
MOs are empty.
Figure 1.3
anti-bonding
ψ6
The double bond in but-1-ene,
CH3CH2CH=CH2, is fixed ψ4 ψ5
between C-1 and C-2; that is, it
is localized. However, the double
bonds in buta-1,3-diene, Energy
CH2=CH–CH=CH2 are not
localized, but are spread over the
whole molecule, and are said to
ψ2 ψ3
be delocalized:
ψ1
CH2 CH CH CH2 bonding
Atomic orbitals Molecular orbitals
The same applies to the double
bonds in benzene:

This arrangement accounts for the extra stability or aromaticity of

benzene. The six overlapping p orbitals can be pictured as forming a
delocalized π-electron cloud comprising of two rings (think of them
as doughnuts!), one above and one below the molecular plane as shown
in Figure 1.4. There are no localized C=C bonds as there are in alkenes.
The MOs of benzene are shown pictorially in Figure 1.5. The stability
of a MO is related to the number of nodes it possesses; that is to say,
the number of times the wave function changes phase (sign) around the
ring system. The most stable form has no nodes, when there is a bond-
Figure 1.4 ing interaction between all six adjacent carbon atoms.
 Aromaticity 5

anti-bonding A node is a point where the

+ – amplitude of a wave is zero:
•
ψ6 • •
– + 6 nodes (least stable) nodes

Amplitude
• •
+ • –
+ +
– + –
+
•
ψ4 ψ5 • •
• • – – 4 nodes Distance
• •
– • +
+
Energy
–
•
ψ2 • • ψ3 + – 2 nodes
+ + •

ψ1 0 nodes (most stable)

bonding
Figure 1.5

1.4 The Hückel Rule

It is important to examine aromaticity in its wider concept at this point.
There are many compounds and systems besides benzene that are
aromatic. They possess common features in addition to planarity
and aromatic stability. MO calculations carried out by Hückel in the
1930s showed that aromatic character is associated with planar cyclic
molecules that contained 2, 6, 10, 14 (and so on) π-electrons. This series
of numbers is represented by the term 4n + 2, where n is an integer, and
gave rise to Hückel’s 4n + 2 rule that refers to the number of π-electrons
in the p-orbital system. In the case of benzene, n = 1, and thus the system
contains six π-electrons that are distributed in MOs as shown above.

Box 1.1 Hückel’s Rule

A planar, cyclic system of unsaturated atoms containing (4n + 2)
π-electrons will be aromatic, where n is a positive integer or zero.
It will possess extra stabilization. Some slight deviation from pla-
narity is allowed. A similar system but containing 4n π-electrons
will be anti-aromatic. Not only will it lack aromatic stabilization,
but the closed loop of π-electrons will result in additional destabi-
lization with respect to that anticipated.
These ideas are predicted by calculation and are confirmed by
experiment.
6 Aromatic Chemistry

This rule is now an important criterion for aromaticity. Those systems

that contain 4n π-electrons are unstable and are referred to as anti-
aromatic compounds.
Degenerate orbitals have equal
The reason for the success of the Hückel rule in predicting aromatic-
energies. ity lies in the derivation of the π MOs. For cyclic conjugated molecules,
the energy levels of the bonding MOs are always arranged with one low-
The presence of electrons in anti-
est-lying MO followed by degenerate pairs of orbitals. The anti-bonding
bonding orbitals is destabilizing.
Orbitals that fall on the energy orbitals are arranged inversely, with sets of two degenerate levels and a
reference line are called single highest energy orbital. In the case of benzene, it requires two
nonbonding orbitals; the presence electrons to fill the first MO and then four electrons to fill each of the n
of electrons in these orbitals has
no influence on the total bonding. succeeding energy levels, as illustrated in Figure 1.3. A filled set of bond-
ing MOs results in a stable system. This idea is very like that which links
the stability of the noble gases to a filled set of atomic orbitals.

Worked Problem 1.1

Q Draw MO diagrams for the π-electron systems of cyclobutadi-
ene and cyclooctatetraene.

A There is a simple system for predicting energy levels of MOs in

cyclic systems. A polygon is inscribed within a circle with an apex
at the base and horizontal lines are drawn at the points where the
polygon touches the circle. The number of points of contact and
their position determines the nature of the orbital and the relative
energy. A non-bonding orbital results when the polygon touches
the circle at a horizontal diameter. Touching below this line indi-
cates bonding orbitals of lower energy; these are filled with elec-
trons first, in accord with Hund’s rule. Contact points above the
horizontal diametric line correspond to higher energy anti-bonding
orbitals. This is illustrated in Figure 1.6 for cyclobutadiene, ben-
zene and cyclooctatetraene, having four, six, and eight carbon
atoms, respectively. It can be seen that of these examples only
benzene obeys Hückel’s 4n + 2 rule; both cyclobutadiene and
cyclooctatetraene apparently have unpaired electrons. However,
cyclooctatetraene is not planar, existing in a tub shape, and it
behaves as a polyalkene with all the π-electrons paired up.

Four C atoms Six C atoms Eight C atoms

Figure 1.6

This method can also be used for other simple monocyclic

systems that can be inscribed in a circle.
 Aromaticity 7

Although adherence to the Hückel rule is a valuable test for aromaticity, The chemical shift of the
other properties are also used to assess whether a compound is aromatic resonance signal of a proton, δH,
is measured relative to a
or not. One such diagnostic tool is 1H NMR spectroscopy. When exposed standard, tetramethylsilane,
to a magnetic field, the π-electron cloud circulates to produce a ring (CH3)4Si, for which δH is 0.00
current that generates a local magnetic field (Figure 1.7). This new field ppm. It reflects the chemical
environment of the proton. A
boosts the applied magnetic field outside the ring. As a result, the similar situation applies to the
hydrogen atoms are deshielded and resonate at a lower applied field, resonance signal δC for a 13C
usually in the range δ 6.5–8.5 ppm. Alkenyl hydrogen atoms are also nucleus.
deshielded, but to a lesser extent and normally resonate in the region δ
Aromatic compounds also show
4.5–5.5 ppm. The local field inside the ring opposes the applied field characteristic infrared and
and this effect is apparent in the 1H NMR spectra of the annulenes (see ultraviolet absorption spectra. In
p. 11). the mass spectrum of aromatic
substances, peaks corresponding
to ions such as C6H5+ and C6H6+
are often seen. A commonly
1.4.1 2π-Electron Systems observed peak occurs at m/z 91,
corresponding to the stable ion
Aromatic systems that obey Hückel’s 4n + 2 rule where n = 0 and so C6H5CH2+. These features are all
possess two π-electrons do exist and are indeed stable. The smallest helpful in assigning aromatic
possible ring is three membered and the derived unsaturated structure is character.
cyclopropene. The theoretical loss of a hydride ion from this molecule
leads to the cyclopropenyl cation, which contains two π-electrons
distributed over the three carbon atoms of the planar cyclic system
Applied
(Figure 1.8). magnetic
field
B0
H H
H H
sp3 –H– +
+
Figure 1.7

A circle with a charge inside it

sp2 sp2 and inscribed within a ring
non-planar planar structure is used to denote a (4n
not aromatic “aromatic” + 2) π-electron system.
2π-electron system 2π-electron system
Figure 1.8

This cationic species and a number of its derivatives have been pre-
pared and they are quite stable, despite the strain associated with the
internal bond angles of only 60°. For example, the reaction of hydrogen
bromide with diphenylcyclopropenone, which is itself a stable compound
with aromatic character, gives the diphenylcyclopropenium salt (Scheme
1.1).

Ph Ph
HBr
O + OH Br–
Ph Ph Scheme 1.1
8 Aromatic Chemistry

Examination of the cyclobutadiene system indicates that it possesses

four π-electrons and is thus an unstable 4n system. Cyclobutadiene itself
only exists at very low temperatures, though some of its derivatives are
stable to some extent at room temperature. Cyclobutadiene is a rectan-
gular diene. Loss of two electrons through the departure of two chloride
ions from the 3,4-dichlorocyclobutene derivative creates a 2π-electron
aromatic system, the square, stable cyclobutenyl dication (Scheme 1.2).

Me
Me Me Me
Cl SbF5
2+ 2SbF5Cl–
Cl SO2
Me Me Me
Me
Scheme 1.2

1.4.2 6π-Electron Systems

We have seen that benzene fits into this category, but there are a num-
ber of other stable aromatic systems that contain six π-electrons.
Cyclopentadiene is surprisingly acidic (pKa ca. 16) for a hydrocarbon.
This property arises because the cyclopentadienyl anion, generated by
A curly (or curved) arrow, =, is
used to show the movement of abstraction of a proton by a base such as sodium ethoxide (Scheme 1.3),
an electron pair. has a delocalized aromatic set of six π-electrons.

–
..

..
–
..

–
..

–
..–
H H –
OEt
..

Scheme 1.3 The cyclopentadienyl anion 13 is an efficiently resonance-stabilized

anion in which all the carbon–carbon bond lengths are equal (Figure
1.9). It forms stable compounds, of which ferrocene (14) is an example,
which undergo aromatic substitution reactions such as sulfonation and
acetylation.
In contrast, it is the resonance-stabilized cation derived from cyclo-
heptatriene that possesses the aromatic sextet of π-electrons. Tropylium
bromide is formed by the addition of bromine to cycloheptatriene and

Fe
–
–
..–
13 14
Figure 1.9
 Aromaticity 9

then loss of hydrogen bromide by heating. It can also be generated direct- Unlike cyclopentadiene,
ly from cycloheptatriene by hydride ion abstraction using triphenylcar- cycloheptatriene is not an acidic
hydrocarbon; its pKa is about 36.
benium perchlorate (Scheme 1.4). In the tropylium ion 15, the bond If a proton could be abstracted
lengths are equal and all seven carbon atoms share the positive charge from cycloheptatriene, the
(Figure 1.10). resulting anion would have eight
π-electrons and would be an
unstable, anti-aromatic system.
H
H Ph3C+ ClO4–
+ ClO4– + Ph3CH
hydride ion
abstraction
15
Scheme 1.4

+ +

15
Figure 1.10

Worked Problem 1.2

Q Write an equation to show the formation of the cyclohepta-
trienyl cation by addition of bromine to the hydrocarbon. Use curly
arrows to illustrate the stabilization of the cation.

A Bromine adds to one double bond of cycloheptatriene in exact-

ly the same way as it does to ethene (although conjugate 1,4- and
1,6-addition may be the preferred mode of reaction).
Dehydrobromination occurs on heating. The driving force for the
loss of bromide ion is the extra stability of the resulting cation. The
positive charge is delocalized over the whole system (Scheme 1.5).

H H
H H
Br2 –HBr –Br–
Br +
Br
Br H H

+ +
etc.
+
Scheme 1.5
10 Aromatic Chemistry

A dipole moment is associated Azulene (16) is a stable, blue solid hydrocarbon that undergoes typical
with a permanent uneven sharing electrophilic aromatic substitution reactions. It may be regarded as a
of electron density in a molecule.
It is a vector quantity that combination of 13 and 15; in keeping with this it has a dipole moment
depends on the size of the partial of 0.8 D (Figure 1.11). The fusion bond linking the two rings is longer
charges in the molecule and the (150 pm) than the other bonds (139–140 pm), indicating that azulene is
distance between them, and is
measured in units of Debye (D).
a peripherally conjugated system.
For example, chlorobenzene has
a dipole moment of 1.75 D,
oriented towards the chlorine. In
1,4-dichlorobenzene, the
– +
individual moments directed
towards the chlorine atoms are
equal and opposed to each 16
other. Consequently, the dipole
moment of this molecule is zero.
Figure 1.11

Some heterocyclic compounds possess aromatic character. One such

important compound is pyridine (17), in which one of the CH units of
benzene has been replaced by a nitrogen atom (Figure 1.12). Although
the chemistry of pyridine shows several important differences from
N N
.. benzene, it also has some common characteristics. The five carbon atoms
17 and the nitrogen atom each provide one electron for the π-cloud, there-
by conferring aromaticity on pyridine according to Hückel’s rule. Notice
that the nitrogen retains a lone pair of electrons in an sp2 orbital directed
away from the ring; this accounts for the basic properties of pyridine.
.. Similarly, the five-membered heterocycle pyrrole (18) is aromatic,
N N
H although this molecule obeys Hückel’s rule only because the nitrogen
H
atom contributes two electrons to the π-cloud. In this respect, pyrrole is
18
analogous to the cyclopentadienyl anion. As a consequence, the nitro-
Figure 1.12 gen atom does not retain a lone pair of electrons and pyrrole is not basic.

Addition of two electrons to

cyclooctatetraene would lead to a 1.4.3 10π-, 14π- and 18π-Electron Systems
10π-electron system, the
cyclooctatetraenyl dianion. The most important 10π carbocyclic system is naphthalene (19) in which
Cyclooctatetraene, which is non- two benzene rings are fused together. The fused systems anthracene (20)
planar, reacts with potassium in and phenanthrene (21) obey Hückel’s rule, where n = 3, and have 14π-
tetrahydrofuran to give
dipotassium cyclooctatetraenide,
electrons. All three compounds are typically aromatic and their chem-
which is planar. The C–C bond istry is similar to that of benzene, as discussed in Chapter 12.
lengths are all the same (141
pm). At low temperatures, a
dication is formed when
cyclooctatetraene reacts with
SbF5. This also has some
aromatic characteristics in
keeping with a 6π-electron
system. 19 20 21
 Aromaticity 11

In 1962, Sondheimer prepared a series of conjugated monocyclic poly-

enes called annulenes, with the specific purpose of testing Hückel’s rule.
Amongst the annulenes prepared, compound 22 with 14 and compound
23 with 18 carbon atoms, that is n =3 and n = 4, respectively, have the
magnetic properties required for aromatic character, but behave chemi-
22
cally like conjugated alkenes. In [18]annulene (23), the hydrogen atoms
on the outside of the ring resonate in the aromatic region at δ 9.3 ppm.
However, the inner protons lie in the region where the induced field asso-
ciated with the ring current opposes the applied field. They are therefore
shielded and so resonate upfield at δ –3.0 ppm.

1.5 Nomenclature
23
The remainder of this book will be devoted to the synthesis and reactions
of a range of aromatic compounds. It is important that you understand
the naming of these compounds. The use of trivial names is widespread,
particularly in the chemical industry; although some of the older names
have disappeared from use, many persist and are allowed in the IUPAC
system. Some of these are presented in Figure 1.13.

O OH
Me NH2 OMe OH

Benzene Toluene Styrene Aniline Benzoic acid Anisole Phenol

Methylbenzene Phenylethene Phenylamine Benzenecarboxylic acid Methoxybenzene Hydroxybenzene

Monosubstituted compounds are commonly named as in aliphatic Figure 1.13

chemistry, with the substituents appearing as a prefix to the parent name
benzene; bromobenzene, chlorobenzene and nitrobenzene are examples
(Figure 1.14).

Br Cl NO2

Bromobenzene Chlorobenzene Nitrobenzene

Figure 1.14

There are two acceptable ways of naming the three positional isomers
that are possible for disubstituted benzene rings. The substituent
12 Aromatic Chemistry

X X positions 1,2-, 1,3- and 1,4- are sometimes replaced by the terms
ortho-, meta- and para- (abbreviated to o-, m- and p-, respectively) (see
2 ortho
24 and 25). You are advised to become familiar with both systems so
3 meta that you can use them interchangeably.
4 para In multiply substituted compounds, the groups are numbered so that
24 25
the lowest possible numbers are used. The substituents are then listed in
alphabetical order with their appropriate numbers. Examples are given
in Figure 1.15, which also introduces further trivial names.

Br Me
Br NH2

Me Cl
o-Dibromobenzene m-Xylene p-Chloroaniline
1,2-Dibromobenzene 1,3-Dimethylbenzene 4-Chlorophenylamine

Me Cl OMe
Br NO2 OH

NO2 Cl H
2-Bromo-4-nitrotoluene 1,4-Dichloro-2-nitrobenzene 4-Hydroxy-3-
Figure 1.15 methoxybenzaldehyde

There are occasions when the benzene ring is named as a substituent

and in these cases the name for C6H5- is phenyl, abbreviated to Ph. The
name for C6H5CH2- is benzyl or Bn, whilst the benzoyl substituent is
C6H5CO- or Bz. These substituents can also be named systematically as
shown in Figure 1.16.

H O

Br Cl

Phenylacetylene Benzyl bromide Benzoyl chloride

Ethynylbenzene (Bromomethyl)benzene Benzenecarbonyl chloride
Figure 1.16
 Aromaticity 13

Summary of Key Points

1. Benzene is an unusually stable molecule. This aromatic stabi-
lization is associated with its 6π-electron system.

2. Other molecules besides benzenoid compounds also show

increased stability.

3. Aromatic stability is found in planar, cyclic conjugated systems

that satisfy the Hückel rule in possessing (4n + 2) π-electrons.

4. (4n + 2) π-electrons corresponds to a completely filled set of

bonding molecular orbitals.

5. Ionic species that comply with all the requirements for aro-
maticity are best regarded as resonance-stabilized ions.

6. Protons in an aromatic environment usually resonate at δ

6.5–8.5 ppm.

7. Cyclic, planar molecules with 4n π-electrons are particularly

unstable and are said to be anti-aromatic.

8. Substitution reactions, which are the most important type shown

by aromatic compounds, conserve aromatic stability.

9. Addition reactions, which are less common, destroy the aromatic

system.

Problems
1.1. Draw the MO diagrams of the π-electron system for the fol-
lowing species: the cyclopropenyl radical, the cyclopropenyl cation,
the cyclobutadienyl cation, the cyclopentadienyl anion, the tropy-
lium cation, the cyclooctatetraenyl dication.

1.2. Cyclopropenones are described as having aromatic character.

How would you account for this, given that the ring contains three
π-electrons?

1.3. Which of the following compounds would you expect to be

aromatic:
14 Aromatic Chemistry

– Na+
S O
Me

1.4. Give the systematic names for the following compounds:

NH2 CO2H
Br

Cl HO3S H2N NO2

NO2
(a) (b) (c)

OH Cl
Cl CO2H

Cl
(d) (e)

1.5. Draw structures for the following compounds: (a) 4-chloro-

3-nitrobenzoic acid; (b) m-nitroethylbenzene; (c) 2,6-dibromo-4-
nitroaniline; (d) p-chlorobenzenesulfonic acid; (e) o-nitrobenzalde-
hyde