Benzene and

its derivates
(Worked by: Evis Baba,Samanda Babaj,
Levisa Bushati, Dejan Kraja,Rajan Tafa)
Table of contents
What is benzene and Nomenclature of
01 02
its derivates? benzene

Chemical properties of
03 Synthesis of benzene 04
and its derivates benzene and its derivates

05 Three mechanisms of benzene

01
What is benzene and
its derivates?
(General properties)
 Benezene and its derivatives
● Benzene is a colorless, highly flammable, and aromatic organic
compound with the molecular formula C6H6.
● It is a cyclic hydrocarbon with a ring of six carbon atoms, each of
which is bonded to two hydrogen atoms.
● The carbon-carbon bonds in the ring are all of equal length and
strength, which makes benzene a highly stable molecule.
● Benzene and its derivatives are widely used in various industries,
including the production of plastics, synthetic fibers, rubber,
detergents, and pharmaceuticals.
● Some common benzene derivatives include toluene, phenol, aniline,
styrene, and benzoic acid.
Some common benzene derivatives
● Toluene is a colorless liquid with a sweet odor that is widely used as a
solvent in industry.
● It is also used in the production of plastics, synthetic fibers, and rubber.
● Phenol is a white crystalline solid with a distinctive odor that is used in
the production of plastics, dyes, and pharmaceuticals.
● It is also used as an antiseptic and disinfectant.
● Benzoic acid is a colorless crystalline solid with the chemical formula
C6H5COOH that is found naturally in many fruits and plants,
including berries, cinnamon, and cloves.
● Benzoic acid is also commonly used as a food preservative to inhibit the
growth of bacteria, yeast, and mold.
 Some general properties of benzene and its
derivatives
● Aromaticity: Benzene and its derivatives exhibit a unique type of chemical bonding
known as aromaticity, which gives them high stability and unique chemical properties.

● Solubility: Benzene and its derivatives are generally insoluble in water but are soluble
in organic solvents such as ethanol, ether, and chloroform.

● Toxicity: Some benzene derivatives can be toxic and even carcinogenic if ingested or
inhaled in large quantities.

● Reactivity: Benzene and its derivatives can undergo a variety of chemical reactions,
such as substitution, addition, and oxidation, which make them useful in many
industrial applications.

● Odor: Some benzene derivatives have characteristic odors, which can range from
sweet and pleasant (e.g., aniline) to pungent and irritating (e.g., phenol).
A structure of benzene
 02

Nomenclature of
benzene
Nomenclature of Mono-Substituted Derivatives of
Benzene
● Monosubstituted derivatives of benzene are named systematically using
benzene as the parent and listing the substituent as a prefix.
Common Names for Mono-Substituted Benzenes
● If the substituent is larger than the benzene ring (if the substituent has more than
six carbon atoms), then the benzene ring is treated as a substituent and is called a
phenyl group.

● The presence of phenyl groups is often indicated with the letters Ph or with the
Greek letter phi (ᵩ)
 Nomenclature of Disubstituted Derivatives of Benzene

● Dimethyl derivatives of benzene are called xylene, and there are three constitutionally
isomeric xylenes.

● These isomers differ from each other in the relative positions of the methyl groups and can
be named in two ways: (1) using the descriptors ortho- (o-): 1,2- (next to each other in a
benzene ring), meta- (m): 1,3- (separated by one carbon in a benzene ring), and para (p):
1,4- (across from each other in a benzene ring).
03
Synthesis of benzene and its
derivates
Methods for Synthesizing Benzene and its Derivatives

● There are many ways to synthesize

benzene and its derivatives,
depending on the starting materials
and desired products.

● Here are a few common methods:

 Catalytic Reforming
● This is the most common
method of producing benzene
from petroleum.
● The process involves heating a
mixture of hydrocarbons in the
presence of a catalyst such as
platinum or aluminum oxide,
which breaks down larger
molecules into smaller ones and
rearranges the atoms to form
benzene.
 Friedel-Crafts Acylation
RCOCl + C6H6 → RCO-C6H5 + HCl
● Friedel-Crafts acylation of
benzene is a chemical
reaction that involves the
substitution of a hydrogen
atom on a benzene ring with
an acyl group (RCO-),
typically using an acid
chloride (RCOCl) as the
acylating agent and a Lewis
acid catalyst, such as
aluminum chloride (AlCl3).
 Halogenation
● This method is used to introduce a
halogen group (-X, where X is a
halogen such as Cl or Br) onto a
benzene ring.
● The reaction is carried out with a
halogenating agent such as
chlorine or bromine in the
presence of a Lewis acid catalyst.

C6H6 + Cl2 → C6H5Cl + HCl

 Other Methods for Synthesizing Benzene and
its Derivatives
● Friedel-Crafts Alkylation:
o This method is used to add an alkyl group (-R) to a
benzene ring.
o The reaction is catalyzed by a strong Lewis acid such as
aluminum chloride and proceeds through the formation
of a carbocation intermediate.

● Nitration:
o Nitration happens when one (or more) of the hydrogen
atoms on the benzene ring is replaced by a nitro group,
NO2. Benzene is treated with a mixture of concentrated
nitric acid and concentrated sulfuric acid at a
temperature not exceeding 50°C.
 04

Chemical properties of benzene

and its derivates
 Combusion reaction
● Benzene and its derivatives undergo combustion reactions in
the presence of oxygen to produce carbon dioxide, water, and
heat. The general equation for the combustion of benzene is:
C6H6 + 15/2 O2 → 6 CO2 + 3 H2O + heat
● For example, the combustion of toluene can be represented
by the equation:
C7H8 + 9 O2 → 7 CO2 + 4 H2O + heat
 Halogenation of benzene and its
derivatives
● Benzene and its derivatives react with halogens (chlorine, bromine) in the
presence of a catalyst (such as iron or aluminum chloride) to form
halogenated products.
● The reaction is typically slower than halogenation of alkanes due to the
stability of the aromatic ring.
● The general equation for the halogenation of benzene is:
C6H6 + X2 → C6H5X + HX
● where X represents the halogen. For example, the chlorination of benzene
yields chlorobenzene:
C6H6 + Cl2 → C6H5Cl + HCl
● Similarly, toluene can be chlorinated to form chlorotoluene:
C7H8 + Cl2 → C7H7Cl + HCl
Alkylation of benzene and its derivative
● Benzene and its derivatives can undergo alkylation reactions, in
which an alkyl group is added to the aromatic ring.
● This reaction can be catalyzed by strong acids, such as sulfuric
acid or hydrofluoric acid.
● The general equation for the alkylation of benzene is:
C6H6 + R-X → C6H5-R + HX

● where R represents an alkyl group and X represents a halogen.

For example, toluene can be alkylated to form ethylbenzene:

C7H8 + C2H5-X → C6H5-C2H5 + HX

 Nitration of benzene and its derivatives
● Benzene and its derivatives can be nitrated to form
nitroaromatic compounds, which are important intermediates
in the production of dyes, explosives, and pharmaceuticals.
● The reaction is typically carried out using a mixture of nitric
and sulfuric acids.
● The general equation for the nitration of benzene is:
C6H6 + HNO3 → C6H5NO2 + H2O

● For example, toluene can be nitrated to form ortho-

nitrotoluene:
C7H8 + HNO3 → C7H7NO2 + H2O
Oxidation of benzene and its derivatives

● Benzene and its derivatives can undergo oxidation reactions,

in which the aromatic ring is partially or completely oxidized.
● For example, benzoic acid can be oxidized to form benzene-
1,2,3-tricarboxylic acid.
● However, this reaction is typically not used for industrial
production of benzene derivatives, as it is not practical or
cost-effective.
 05

Three mechanisms of benzene

 Halogenation of benzene
● The halogenation of benzene involves the substitution of one or more hydrogen atoms on
the benzene ring with a halogen atom, such as chlorine or bromine.
● The reaction is typically carried out in the presence of a halogen carrier catalyst, such as
iron(III) chloride, FeCl3.
● The mechanism for the halogenation of benzene involves a series of steps, including:

1. Generation of the electrophile: The halogen carrier catalyst reacts with the halogen to form a
halonium ion, which acts as an electrophile.

2. Formation of the arenium ion: The electrophile attacks the benzene ring, forming a complex known as
an arenium ion or sigma complex. This intermediate is stabilized by resonance.

3. Rearrangement and loss of the catalyst: The arenium ion undergoes a rearrangement to restore the
aromaticity of the benzene ring. The catalyst is also lost during this step.

4. Deprotonation: The final step involves the removal of a proton from the aromatic ring, resulting in the
substitution of a hydrogen atom with the halogen atom.
 Alkylation of benzene
● The alkylation of benzene involves the substitution of one or more hydrogen atoms
on the benzene ring with an alkyl group, such as methyl or ethyl.
● The reaction is typically carried out in the presence of an acid catalyst, such as
aluminum chloride, AlCl3.
● The mechanism for the alkylation of benzene involves a series of steps, including:

1. Formation of the carbocation: The acid catalyst reacts with the alkyl halide to generate a
carbocation, which acts as an electrophile.

2. Formation of the arenium ion: The carbocation attacks the benzene ring, forming an arenium ion
or sigma complex. This intermediate is stabilized by resonance.

3. Rearrangement and loss of the catalyst: The arenium ion undergoes a rearrangement to restore
the aromaticity of the benzene ring. The acid catalyst is also lost during this step.

4. Deprotonation: The final step involves the removal of a proton from the aromatic ring, resulting in
the substitution of a hydrogen atom with the alkyl group.
 Nitration of benzene
● The nitration of benzene involves the substitution of one hydrogen atom on the
benzene ring with a nitro group, NO2.
● The reaction is typically carried out in the presence of a mixture of nitric acid
and sulfuric acid.
● The mechanism for the nitration of benzene involves a series of steps, including:

1. Formation of the nitronium ion: The nitric acid reacts with the sulfuric acid to form a nitronium
ion, NO2+.

2. Formation of the arenium ion: The nitronium ion attacks the benzene ring, forming an arenium ion
or sigma complex. This intermediate is stabilized by resonance.

3. Rearrangement and loss of the catalyst: The arenium ion undergoes a rearrangement to restore
the aromaticity of the benzene ring. The sulfuric acid catalyst is also lost during this step.

4. Deprotonation: The final step involves the removal of a proton from the aromatic ring, resulting in
the substitution of a hydrogen atom with the nitro group.