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 DEPTH OF BIOLOGY

REACTION OF BENZENE

•NITRATION
•SULPHONATION
•HALOGENATION
•FRIDEL CRAFT ALKYLATION & ACYLATION
 DEPTH OF BIOLOGY

NITRATION
• The introduction of NO2 (nitro group) on
benzene
• Substitution of 1 hydrogen atom by NO2
is known as nitration of benzene
• Nitrobenzene is formed with chemical
formula- C6H5NO2
 DEPTH OF BIOLOGY

NITRATION
• This reaction takes place in the presence
of following reagents-
1. Nitric acid -HNO3
2. Concentrated Sulphuric acid - H2SO4
(king of acid)
 DEPTH OF BIOLOGY

NITRATION MECHANISM
• OH- is released by HNO3
so only NO2 (nitronium ion)
remains which gets attached to
benzene to form nitrobenzene

• H+ is donated by conc. H2SO4 so HSO4- remains.

• H+ & OH- combines to give water
DEPTH OF BIOLOGY
 DEPTH OF BIOLOGY

NITRATION

HNO3

+ H2O
conc.
H2SO4
 DEPTH OF BIOLOGY

APPLICATION OF NITRATION
•Majorly, nitration process chemistry in industry is utilised for making explosives.
For instance, a Nitration reaction is used to form nitroguanidine from guanidine. The
changing reaction of toluene structure (C 7H8) to (TNT) / trinitrotoluene.

•Another significant use of nitration chemistry in the industry is the nitrated product
called Dinitrotoluene. DNT/ Dinitrotoluene is transformed into toluene diisocyanates
(toluene structure). The latter has its application in the production of elastomers,
fibres, polyurethane foams and varnishes.

•Furthermore, they have wife applications as precursors for a reaction and as

chemical intermediates in the reaction process and precursors.
 DEPTH OF BIOLOGY

REACTION OF BENZENE

•NITRATION
•SULPHONATION
•HALOGENATION
•FRIDEL CRAFT ALKYLATION & ACYLATION
 DEPTH OF BIOLOGY

SULPHONATION
• Sulphonation of benzene is a chemical process
where a sulphonic acid group SO3H is added to
benzene ring
• Sulphonation can be done in presence of conc.
H2SO4 or H2S2O7 (oleum)
• 2 molecules of concentrated sulphuric acid are
required
 DEPTH OF BIOLOGY

SULPHONATION MECHANISM
• 1 molecule of H2SO4 donates H+ ion while other releases OH-
• This together forms H2O
• Back bonding between hydrogen and sulphur is also possible

H+ OH-

H2O
 DEPTH OF BIOLOGY

SULPHONATION
• Now, SO3H is left which attacks the benzene ring and forms benzenesulphonic acid
 DEPTH OF BIOLOGY

SULPHONATION

Oleum
H2S2O7
 DEPTH OF BIOLOGY

SULPHONATION APPLICATION
•One common application is in the production of detergents and cleaning agents. The sulfonic
acid group added to benzene enhances its solubility in water, making it useful in formulating
surfactants for cleaning purposes.

•It is also used in the synthesis of dyes, pharmaceuticals, and certain types of polymers

•Benzene sulphonation has a variety of applications beyond detergents and cleaning agents.

•It is commonly used in the production of sulfonated aromatic compounds, which are used as
intermediates in the synthesis of various chemicals, including dyes, pigments, and
pharmaceuticals.

•Additionally, benzene sulphonation plays a role in the production of certain types of resins,
plasticizers, and even flavors and fragrances. It's a versatile process with many practical uses.
 DEPTH OF BIOLOGY

REACTION OF BENZENE

•NITRATION
•SULPHONATION
•HALOGENATION
•FRIDEL CRAFT ALKYLATION & ACYLATION
 DEPTH OF BIOLOGY

HALOGENATION
• Halogenation is a process in which one hydrogen is
substituted by halogen atom like Cl, Br, I
• Fluorine {F} is not used because it is highly
electronegative element
• Generally Cl is introduced – chlorination
• When Br is introduced – Bromination
• Iodine [I] is introduced- iodination
 DEPTH OF BIOLOGY

HALOGENATION
CL2 chlorobenzene

AlCl3

Br2
• // FeBr3
bromobenzene

I2

HNO3 Iodobenzene
 DEPTH OF BIOLOGY

MECHANISM
• Cl – Cl bond is easily breakable, so the bond breaks
giving partial negative and positive charges to
chlorine molecules
• In AlCl3 Al carries negative charge while Cl carries
positive charge so the Cl with partial negative
charge attacks and forms AlCl4
• While other chlorine molecule attaches to benzene
and forms nitrobenzene
DEPTH OF BIOLOGY
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MECHANISM
• Same mechanism is followed for bromine and
iodine
 DEPTH OF BIOLOGY

APPLICATION
• One common application is in the production of halogenated
solvents, which are used as cleaning agents, degreasers, and
as intermediates in chemical synthesis.
• Halogenated benzene compounds are also used in the
manufacturing of pharmaceuticals, dyes, and agrochemicals.
• Additionally, certain halogenated benzene derivatives have
applications in the field of organic electronics and materials
science
 DEPTH OF BIOLOGY

REACTION OF BENZENE

•NITRATION
•SULPHONATION
•HALOGENATION
•FRIDEL CRAFT ALKYLATION & ACYLATION
 DEPTH OF BIOLOGY

FRIEDEL CRAFT ALKYLATION

• It is a chemical reaction involving introduction of
alkyl group on benzene and creating alkylbenzene.
• A Lewis acid catalyst such as FeCl3 or AlCl3 is
employed in this reaction
• Alkyl halides are also involved
 DEPTH OF BIOLOGY

MECHANISM
• Alkyl halide reacts with Aluminum chloride to form
Tetrachloroaluminate as Cl carries negative charge
hence R group is released which attacks benzene
and form alkylbenzene

• R- Cl + Al Cl3 AlCl4
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MECHANISM
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MECHANISM
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Limitations
• Since the carbocations formed by aryl and vinyl halides are extremely
unstable, they cannot be used in this reaction.
• The presence of a deactivating group on the aromatic ring (such as an
NH2 group) can lead to the deactivation of the catalyst due to the formation
of complexes.
• An excess of the aromatic compound must be used in these reactions in
order to avoid polyalkylation (addition of more than one alkyl group to the
aromatic compound).
• Aromatic compounds that are less reactive than mono-halobenzenes do not
participate in the Friedel-Crafts alkylation reaction.
• It is important to note that this reaction is prone to carbocation
rearrangements, as is the case with any reaction involving carbocations.
 DEPTH OF BIOLOGY

Application
• One common application is in the production of alkylated
aromatic compounds, which are used in the manufacturing of
pharmaceuticals, fragrances, and dyes.
• It can also be used to synthesize polymers with specific
properties. Additionally, Friedel-Crafts alkylation plays a
crucial role in the synthesis of various organic intermediates
and fine chemicals.
• It's a versatile reaction that allows chemists to introduce alkyl
groups onto aromatic rings, expanding the range of
compounds that can be synthesized.
 DEPTH OF BIOLOGY

FRIEDEL CRAFT ACYLATION

• The Friedel-Crafts acylation reaction involves the
addition of an acyl group to an aromatic ring.
• Typically, this is done by employing an acid chloride
(R-(C=O)-Cl) and a Lewis acid catalyst such as AlCl3.
• In a Friedel-Crafts acylation reaction, the aromatic
ring is transformed into a ketone.
 DEPTH OF BIOLOGY

FRIEDEL CRAFT ACYLATION

 DEPTH OF BIOLOGY

MECHANISM
O δ+ δ-

R- C –Cl + AlCl3 AlCl4 +

• Al will donate electron to Cl and create a negative

charge on it hence AlCl4 formation will take place
• R-(C=O) will remain and get attached to benzene
 DEPTH OF BIOLOGY

MECHANISM
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LIMITATION
• Despite overcoming some limitations of the related alkylation reaction (such as
carbocation rearrangement and polyalkylation), the Friedel-Crafts acylation
reaction has a few shortcomings.
• The acylation reaction only yields ketones. This is because formyl chloride
(H(C=O)Cl) decomposes into CO and HCl when exposed to these conditions.
• The aromatic compound cannot participate in this reaction if it is less reactive than
a mono-halobenzene.
• Aryl amines cannot be used in this reaction because they form highly unreactive
complexes with the Lewis acid catalyst.
• The acylations can take place on the nitrogen or oxygen atoms when amine or
alcohols are used.
 DEPTH OF BIOLOGY

APPLICATION
• One specific application of Friedel-Crafts acylation is in
the synthesis of aspirin, also known as acetylsalicylic
acid. The acylation of salicylic acid with acetic
anhydride using a Lewis acid catalyst, such as sulfuric
acid, results in the formation of aspirin.
• Without Friedel-Crafts reactions we wouldn't be able to
extend aromatic compounds into larger molecules, with
more carbon atoms. So, we would be able to form the
individual rings for DNA but we wouldn't be able to
connect them together to fully form DNA.
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