Aromatic

Compound
Reaction
 Learning
Objective
To know the reaction
mechanism on aromatic
rings and some common
examples
Arene - Review
Arene is one type of functional
group in Organic Chemistry which
includes hydrocarbons with some
general properties. The properties
are:
1. Planar
2. Cyclic
3. Having conjugated double bond
4. sp2 hybridized
Aromatic Compound
Reaction
Because of the conjugated double bond,
aromatic compounds seems like a smoked
beef inside bun; a thin planar compound
surrounded by electron clouds below and
above the compound. The molecule is now
surrounded with negative charge, so in order
to react it with anything, we have to make
them positively charged.
Reactions of Arene
Reactions in arene are also known as
electrophilic substitution. Some of the most
common reactions are:
1. Halogen substitution
2. Alkyl/Acyl substitution
3. Sulfonation
4. Nitration
1. Halogen
Substitution
Regular halogen substitution
can only work on alkane, but
not on arene. To react on
aromatic ring, we have to
make the thing positive first.
It can be done using catalyst.
Examples
1. What is the product of reaction between Naphthalene
(C10H8) and Cl2 gas by the help of heat and UV light?

2. Draw the possible products of the reaction between two

moles of Br2 and Benzene by the help of FeBr3.

3. What is the product of substitution reaction between

Toluene (C7H8) with I2 using:
a. Heat + UV light
b. FeI3
2. Alkyl/Acyl
Substitution
Just like halogen
substitution, alkyl/acyl can
be put in aromatic ring with
the help of catalyst. The
alkyl/acyl group should be
made positive first before it
can react with the ring. The
reaction is also known as
Friedel-Crafts Reaction.
Examples
1. Benzaldehyde can be made by Friedel-Crafts
substitution. Write down the chemical reaction
for benzaldehyde synthesis.

2. Draw the products of reaction between phenol

and ethanoyl chloride with the help of AlCl3.

3. What shall we react with methyl chloride to

produce nitrotoluene?
3. Sulfonation
Sulfonation reaction happens when
we react arenes with concentrated
sulfuric acid (H2SO4). The reaction
happens because the acid are strong
enough to give H+ to SO3, making it
positive, which can be attacked by
aromatic ring.
4. Nitration
The steps in nitration is similar with sulfonation, but
we add Nitric acid to the mixture. After nitric acid
receives proton, it releases water molecule, leaving
NO2+. This ion can be attacked by aromatic ring.
Examples
1. What is the main product of reaction of nitration of
phenol?

2. Draw the product of reaction between toluene and excess

amount of nitric and sulfuric acid.

3. ABS (Alkyl benzene sulfonate) is a common ingredient in

detergent. Suggest reagents needed to produce
Decylbenzene sulfonate.
5. Hydrogenation
The empty p orbitals in
aromatic compound can be
used to make new bond, but
it needs an extra effort. To
make aromatic compound
saturated, we need to use
metal catalyst with
extremely high pressure.
6. Oxidation
Normal alkane can’t be oxidized, but methyl group attached
to aromatic ring can undergo oxidation using strong
oxidizing agent. For example, Toluene can undergo
oxidation forming benzyl alcohol, benzaldehyde, even
benzoic acid.
Examples
1. Aniline, also known as phenylamine, can be synthesized
by two-steps reaction. Suggest how we can synthesize
aniline.

2. What is the product of reaction when Toluene is oxidized

with KMnO4, then reacted with excess H2 gas with
appropriate condition?
Conclusion 1. The reaction condition for arenes are different from
alkene.
2. In order to react, the attacking substance should be
positively charged.
3. Arene can also undergo hydrogenation and
oxidation reaction