BENZENE and

It’s Derivatives
Presented By:IRSHAD KHAN
Final year B.Pharmacy

Royal college of pharmaceutical education and

research,Malegaon
 TABLE OF CONTENTS
01 02
INTRODUCTION AROMATICITY
OF BENZENE
03 04
REACTION OF EFFECTS OF
BENZENE SUBSTITUENT
05 USES

06 REFERENCES
 01
INTRODUCTION
OF BENZENE
 1.1BENZENE
Benzene is one of the most commonly known
aromatic compounds with chemical formula
C6H6. (also c.a.Cyclohexatriene)
History of Benzene:
• Discovered in the year 1825 by Michael Faraday in
illuminating gas.
• 1934 Eilhardt Mitscherlich
1.2 Nomenclature Derivative of
Benzene
For monosubstituted:
For Disubstituted:
For Polysubstituted:
 1.3.Structure of Benzene
The chemical formula for benzene is C6H6, i.e it has 6 hydrogen- H atoms and six-
carbon atoms and has an average mass of about 78.112. The structure has a six-carbon
ring which is represented by a hexagon and it includes 3-double bonds. The carbon
atoms are represented by a corner that is bonded to other atoms.
 Observation supporting unsaturation of
Benzene:
• Benzene can take three molecules of H in presence of catalyst.
• Benzene resist oxidation.
• Benzene forms Triozonide on Reaction with ozone.
• Benzene shows substitution rather than addition reactions.

Three theories of Benzene structure:

• Kekule’s structure of Benzene
• Molicular orbital theory(MOT)
• Resonance structure of Benzene
 Kekule’s structure(1865):
Objection of Kekule’s structure:
• Not explain stability of Benzene.
• Only one monosubstituted product is
known.
• Single and double bond oscillate.
• Benzene is regular hexagon.
 Resonance theory of Benzene:
To explain all the limitation of Kekule’s it has been proposed that benzene is
resonance hybrid of all the three structures-
Molecular orbital theory(MOT):
 02 Aromaticity
2.1.Huckel’s rule:
In 1931, German chemist and physicist Erich Hückel proposed a theory to help determine if a
planar ring molecule would have aromatic properties. His rule states that if a cyclic, planar
molecule has 4n+2 π electrons, it is considered aromatic. This rule would come to be known
as Hückel's Rule.
• Rules:
• The molecule is cyclic (a ring of atoms)
• The molecule is planar (all atoms in the molecule lie in the same plane)
• The molecule is fully conjugated (p orbitals at every atom in the ring)
• The molecule has 4n+2 π electrons (n=0 or any positive integer)
Huckel Rule applied :
3.REACTION OF BENZENE:

3.1.Method of preparation 3.2.Reactivity of benzene

3.1.Method of Preparation:
Reactivity of Benzene:
 04 Effect of Substituents:

4.1 On 4.3.Anomalo
orientation us behaviour
of Halogen
4.2.On
Reactivity
 4.1.On orientation:
a)Ortho-para directing groups: These groups direct the incoming groups to ortho and
para positions. for example, alkyl (R), phenyl (-ROH), halogens (-CI, -Br etc.), hydroxyl
(-), Alkoxy (OR), amino (-NH), Anilide (-NHCOR) etc.

b)Meta directing groups:These groups direct the incoming groups to meta position. for
example, trialkyl ammonium ion (N+R3), nitro (NO), cyano (-CN), aldehyde (- CHO),
ketonic (-COR), carboxylic (-COOH), sulphonic acid (SO3H).
e.g.Ortho-para,meta directing group
 4.2.On Reactivity:
a).Ortho para directing groups having electron
releasing inductive effect(+I effect).
b).Ortho para directing groups having electron
withdrawing inductive effect(-I effect).
c).Meta directing groups.
4.3.Anomalous behaviour of Halogen:

05 Uses:
• Dichloro diphenyl Trichloro Ethane.
• Benzene Hexachloride.
• Saccharin.
 06 References
1. B.S Bahl,Arun Bahl,”Text book of organic Chemistry”Eleventh edition.1967,published
by.S.Chand and company,page.No.659.
2. Morrison And Boyd, "Organic chemistry ”sixth edition,published by.Prentice-Hall of
India,page.No.493-513.
3. Varun Arora,Pragi Arora, Pharmaceutical organic chemistry-II”Edition.2019,published
by.S.Vikas and company,page.No.1-23.
Does anyone have any questions?

THANKS!
HAPPY TEACHERS
DAY