Group Members:

Phua Wan Jien D20091035127

Muhamad Fadlilah Bin Mukhlas D20091035126
Lecturer : Dr. Saripah Salbiah Syed Abdul Azziz
PHUA
PHUAWAN
WANJIEN
JIEN MOHD
MOHDFAD
FAD
D20091035127
D20091035127 D20091035128
D20091035128
 CONTENTS

Inducti Empow
on Set ering
Synthesis of
Benzene

Enhanci Closure
ng
Understanding of
Benzene
 Understanding of
benzene

• In earlier time, compounds are called aromatic because of their

pleasant odours.
• Today, we use the word aromatic to refer to benzene and its
structural relatives.
• Benzene is an organic chemical compound with the molecular
formula C6H6.
• Aromatic compound is a cyclic conjugated molecule or ion
that is stabilized by ∏ electron delocalization.
• It is characterized by substitution reactions.

 
 KEKULÉ STRUCTURE
 Kekule was the first to formulate a reasonable
representation of benzene.

H C H
C C
or
C C
H C H

The Kekule structure suggests alternating double and single carbon-

carbon bonds.
 RESONANCE STRUCTURE

Benzene is actually a resonance hybrid of the two Kekulé structure.

equivalent to

resonance hybrid

• All C-C bond length equal = 139 pm

• Shorter than typical C-C (148 pm)
• Longer than typical C=C (134 pm)
The six p electron completely delocalized around the ring.
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o u n
benzene f

Cigarettes release bet Cigarettes

ween 50 and 150 mic
cigarette, and represe rograms of benzene
nt a significant sourc per
About half of the exp e of benzene exposure
osure to benzene in th .
smoking or being exp e United State comes
osed to cigarette smo from
chemicals present in ci ke . While there are other
garettes that are carcin
benzene is responsib ogens in their own rig
le for one-tenth to o ht,
deaths from leukemia ne -h al f of smoking-related
.
 Synthesis
Of Benzene
 From Sodium Benzoate

From Phenol

From toluene

From acetylene

From chlorobenzene

From benzene sulphonic acid

From benzene diazonium chloride

From Laboratory Method:

•By the decarboxylation of sodium benzoate

•This method is used in the laboratory to obtain benzene.
•Sodium benzoate is heated with soda-lime and when it gets
decarboxylated (removal of carbon dioxide) benzene is
obtained.

                                                             CaO
C6H5COONa                +   NaOH       -------------->     C6H6   +  Na2CO3
Sodium Benzoate
From benzene derivatives:

a) From phenol

•This is reduction of Phenol

•Benzene can be obtained by distilled of
phenol with zinc dust.

                                               distillation
C6H5OH                +   Zn   ---------------------------->     C6H6            +     ZnO
  Phenol
 Ni-Al alloy
C6H5Cl + 2H ---------> C6H6 + HCl
Chlorobenzene NaOH Benzene

b) From toluene:
•Benzene is prepared by hydrodealkylation of toluene. Toluene
mixed with hydrogen is passed over different catalyst such as
chromium, molybdenum etc. at 500 – 600 ‘C. This process gives
benzene and methane.
c) From chlorobenzene:

Chlorobenzene

Ni-Al alloy
C6H5Cl + 2H ------------> C6H6 + HCl
Chlorobenzene NaOH Benzene
e) From benzene sulphonic acid

•Benzene is formed by the hydrolysis with

superheated steam of benzene sulphonic acid.

C6H5SO3H                                +       HOH              ----->  C6H6          +    H2SO4

Benzene sulphonic acid            Steam                    Benzene
f) From benzene diazonium chloride

•This is done by the reduction of benzene diazonium chloride.

•Benzene is formed on the reduction of benzene diazonium
chloride with sodium stannite or hypophosphorus acid.

SnCl2
C6H5N2Cl + 2H ---------> C6H6 + N2 + HCl
NaOH
g) From acetylene

•This is done by polymerisation of acetylene

•When acetylene gas is passed through red hot iron or copper
tubes it polymerises and gives benzene.

                              5000C
3C2H2              ---------------------->   C6H6
Acetylene                                   Benzene
 Testing your understanding

Pick a icon and

answer the
question.
Good luck!
                                   distillation
A     +   Zn   ---------------------------->     C6H6            +     ZnO
  

1) What is the name of substance A?

a) Chlorobenzene
b) Benzene sulphonic acid
c) Phenol

Ans: C
 Ni-Al alloy
X + 2H ------------> C6H6 + Y
NaOH Benzene

2) Name the X and Y?

X Y
a) Phenol water
b) Chlorobenzene Hydrogen chloride
c) benzene diazonium Hydrogen chloride
chloride

Ans: B
4) From the process above, what is the process to get benzene?

a)Polymerisation of acetylene
b) Hydrolysis of superheated steam of acetylene
c)Hydrodealkylation of acetylene

Ans: A
 Well
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 This
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Plea ’t give g.
se tr up.
y ag
ain.
Closure
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