Aromatic 11th

1. Side Chain Reactions

2. Name Reactions
3. Preparation of benzene
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Addition reactions of Benzene Derivatives

When benzene is treated with an excess of chlorine under heat and pressure (or with
irradiation by light), six chlorine atoms add to form 1,2,3,4,5,6-hexachlorocyclohexane.
This product is often called benzene hexachloride (BHC)
Addition reactions of Benzene Derivatives

Catalytic hydrogenation of benzene to cyclohexane takes place at elevated temperatures

and pressures, often catalyzed by ruthenium or rhodium-based catalysts.
Birch Reduction

Partial reduction of aromatic compounds

The reduction of aromatic compounds by alkali metals in liquid ammonia in the presence
of an alcohol is called the Birch reduction, and yields selectively the 1,4-hydrogenated
product.
A carbon bearing an electron-withdrawing carbonyl group is reduced

A carbon bearing an electron-releasing alkoxy group is not reduced

 Birch Reduction

Mechanism
Side Chain Halogenation
Oxidation of Side Chain with KMnO4

An aromatic ring imparts extra stability to the nearest carbon atom of its side chains.
The aromatic ring and one carbon atom of a side chain can survive a vigorous
permanganate oxidation.
Oxidation of Side Chain with KMnO4

Side-chain oxidation is not restricted to alkyl groups. Alkenyl, alkynyl, and acyl
groups are also oxidized by hot alkaline potassium permanganate.
Oxidation of Side Chain with KMnO4

tert-Butylbenzene is resistant to side-chain oxidation. Why?

Addition to double bond of side chain
Preparation of Arenes
Preparation of Arenes
Use of Protecting and Blocking Groups

Very powerful activating groups such as amino groups and hydroxyl groups cause
the benzene ring to be so reactive that undesirable reactions may take place.
Use of Protecting and Blocking Groups
Example The major product obtained in the following reaction:
Example
Example
Reaction in Naphthalene

Naphthalene is an organic compound with formula C10H8. It is the simplest polycyclic

aromatic hydrocarbon.
Reaction in Naphthalene

Polycyclic aromatic hydrocarbons are generally more reactive than benzene in

electrophilic substitution reactions

Electrophilic attack at naphthalene occurs preferentially at C1 to form an intermediate

naphthalenium ion which is more stable than the one formed by attack at C2
Reaction in Naphthalene

● Naphthalenium ion formed by electrophilic addition to C1:

Reaction in Naphthalene

● Naphthalenium ion formed by electrophilic addition to C2:

Example

Which statement is correct?

(a) i form in large quantity

(b) ii form in large quantity
(c) i, ii form in equal quantity
(d) naphthalene does not show nitration
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