Aromatic compounds
PRESENTED BY ROLL NO 12, 08,18,20,28,29,01
Introduction
The term aromatic was drived from Greek word ‘aroma ‘meaning ‘fragrance ‘ •Low
hydrogen to carbon ratio •Almost all aromatic compounds has six carbon unit in their
molecule •e.g:benzene
Aromatic compounds:
The aromatic compounds include benzene and all those compounds that are structurally
related to benzene
Example:Toluene,phenol
Classification of aromatic Hydrocarbon :
1.Monocyclic aromatic hydrocarbon and their derivatives 2.Polycyclic aromatic
hydrocarbon •Monocyclic aromatic hydrocarbon and their derivatives: “Aromatic
compounds Containing one benzene ring in their molecule “ For example:benzene and it’s
derivatives
Polycyclic aromatic hydrocarbon: “Aromatic Hydrocarbon contains two or more benzene
ring in their molecules”
Divided into two classes:
1.Those in which benzene Rings are isolated
For example: Biphenyl
2.Those in which benzene ring are fused together at ortho position so that the adjacent ring
have a common carbon to carbon bond
For example: Naphthalene
Nomenclature
Earlier, most of the compounds with the same structural formula were known by different
names depending on the regions where they were synthesized. This naming system was
very trivial since it raised a lot of confusion. Finally, a common naming system enlisting
standard rules was set up by IUPAC for the naming of compounds.
Examples
IUPAC nomenclature of aromatic hydrocarbons is explained below:
1. According to IUPAC nomenclature of substituted aromatic compounds, the substituent
name is placed as a prefix to the name of aromatic compounds. For example, a benzene
ring attached to a one-nitro group is named as nitrobenzene.
2. When more than one similar substituent group is present in the ring, they are labelled
with the Greek numerical prefixes such as di, tri, tetra to denote the number of similar
substituent groups attached to the ring. If two bromo- groups are attached to the adjacent
carbon atoms of the benzene ring, it is named 1,2-dibromobenzene.
3. When different substituted groups are attached to the aromatic compounds, the
substituent of the base compound is assigned number one and then the direction of
numbering is chosen such that the next substituent gets the lowest number. Substituents
are named in alphabetical order. For example: when chloro and nitro groups are attached
to the benzene ring, we first locate the chloro group then nitro groups.
4. In the case of multiple substituted aromatic compounds, sometimes terms like ortho (o),
meta (m) and para (p) are also used as prefixes to indicate the relative positions 1,2-; 1,3-
and 1,4- respectively. For example, 1,2-Di-bromo-benzene can be named as o-di-bromo-
benzene.
5. When an alkane with a functional group is attached to an aromatic compound, the
aromatic compound is considered as a substituent, instead of a parent. For example: when
a benzene ring is attached to an alkane with a functional group, it is considered as a
substituent named phenyl, denoted by Ph-.
Physical properties of Aromatic compounds
Benzene is a colourless Compound, and the physical state of Benzene is liquid.
Benzene melts at 5.5 °C.
Benzene is not miscible in water and is soluble in organic solvents.
It has an Aromatic odour.
It’s vapors are highly toxic which on inhalation produce loss of consciousness.
The density of Benzene is 0.87 gm/cm3 and is lighter than water.
Benzene exhibits resonance.
It is inflammable, and its combustion produces sooty flames.
Benzene was discovered in 1825 by Michael Faraday.
Benzene has a boiling point of 80.1 °C.
Preparation of Benzene
From acetylene.
Acetylene on passing through a red –hot tube trimerises to give benzene.
Decarboxylaation Of Aromatic Acid.
When sodium benzoate in heated with sodalime, benzene vapours distil over.
Preparation Of Benzene From Phenol
When phenol vapours are passed over zinc dust, then it is reduced to benzene.
Wurtz – Fittig Reaction:
When a solution of bromo benzene and iodo methane in dry ether is treated with metallic
sodium, toluene is formed.
Friedel Craft’s Reaction:
When benzene is treated with methyl chloride in the presence of anhydrous aluminium
chloride, toluene is formed.
Chemical properties
Electrophilic substitution reaction :
Nitration of Benzene
Benzene reacts with concentrated nitric acid at 323-333k in the presence of
concentrated sulphuric acid to form nitrobenzene. This reaction is known as
nitration of benzene.
Sulfunation
Sulfunation of Benzene
Sulfonation of benzene is a process of heating benzene with fuming sulphuric acid
(H2SO4 +SO3) to produce benzenesulfonic acid. The reaction is reversible in nature.
Halogegation
Halogenation of Benzene :
Benzene reacts with halogens in the presence of Lewis acid like FeCl3, FeBr3 to form
aryl halides. This reaction is termed as halogenation of benzene.
Addition reaction
The reaction with chlorine :
The reaction between benzene and chlorine in the presence of either aluminum
chloride or iron gives chlorobenzene.
Addition of Hydrogen :
Hydrogenation is an addition reaction in which hydrogen atoms are added all the
way around the benzene ring. A cycloalkane is formed.
Oxidation reaction
Addition of Oxygen :
Vanadium catalyses the oxidation of benzene to maleic anhydride at 500°C
Uses of Benzene
Benzene is used as a solvent.
Used in the production of rubber.
In the manufacturing of paints and printing.
Used as a fuel.
Used in the production of chemicals and plastic.
Used in Auto Repairs.
Used of Phenol
Phenol is also used in the cosmetic industry in the manufacturing of sunscreens, skin
lightening creams and hair colouring solutions.
Phenol is also used in the study and extraction of bio-molecules.
Approximately two-thirds of the total phenol produced worldwide is used to prepare
reagents used in plastic manufacturing industries.
Uses of Toluene
Toluene is used in the manufacture of synthetic Drugs.
Toluene is used as a solvent for glues paints etc.
It can be used in internal combustion engines as gasoline fuel.
