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PG - M.Sc. - Chemistry - 344 24 - Practical Organic Chemistry - MSC Chemistry

The document outlines the process of nitration of aromatic compounds, specifically benzene, using a nitrating mixture of concentrated nitric and sulfuric acids. It details the required chemicals, procedure, and the mechanism of the reaction, emphasizing the formation of nitronium ions and the resulting products, including nitrobenzene and dinitrobenzene. The document also notes the importance of temperature control during the reaction to influence the product outcome.

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8 views2 pages

PG - M.Sc. - Chemistry - 344 24 - Practical Organic Chemistry - MSC Chemistry

The document outlines the process of nitration of aromatic compounds, specifically benzene, using a nitrating mixture of concentrated nitric and sulfuric acids. It details the required chemicals, procedure, and the mechanism of the reaction, emphasizing the formation of nitronium ions and the resulting products, including nitrobenzene and dinitrobenzene. The document also notes the importance of temperature control during the reaction to influence the product outcome.

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pm102382
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Practical: Organic

ANALYSIS 14. PREPARATION OF ORGANIC Chemistry

COMPOUND ILLUSTRATING
NITRATION
NOTES
Aromatic compounds, such as Phenol, Benzene, etc., can be conveniently
‘Nitrated’ by the use of Nitrating Mixture, which is normally a mixture of
Concentrated Nitric Acid and Concentrated Sulphuric Acid. The nature
of product obtained by the process of Nitration depends on the reaction,
temperature, nature of the compound and nature of the Nitrating Agent.
Nitration happens when one (or more) of the Hydrogen atoms on the Benzene
Ring is replaced by a Nitro Group, NO2.
Following procedures are commonly used.
Chemicals Required
1. Concentrated Nitric Acid
2. Concentrated Sulphuric Acid
3. Sodium Nitrate
4. Dilute Sulphuric Acid
5. Tetranitromethane
6. BF3-Nitrate
Procedure
1. The Nitration of Aromatic Hydrocarbon is usually carried out with
Nitrating Agent at low temperature approximately at 40 to 50°C. High
temperature is avoided.
2. Benzene is treated with a mixture of Concentrated Nitric Acid and
Concentrated Sulphuric Acid at a temperature not exceeding 50°C.
3. The mixture is apprehended at this temperature for about half an hour.
Yellow oily Nitrobenzene is formed.

Alternatively, this reaction is also written as,

Self-Instructional
Material 61
Practical: Organic 4. The function of Sulphuric Acid is to convert Nitric Acid into a highly
Chemistry
reactive, electrophilic, Nitronium Ion . It is highly effectively
Nitrating Agent.
5. The concentrated Sulfuric Acid acts as a catalyst and so is not written
NOTES
into the reaction equations. At higher temperatures, the possibility
is to obtain more than one Nitro group substituted onto the Benzene
ring. A certain amount of 1, 3-Dinitrobenzene is formed at 50°C. Some
of the Nitrobenzene formed reacts with the Nitrating Mixture of the
concentrated acids used. Following is the reaction for the formation
of 1, 3-Dinitrobenzene.

6. The new Nitro group goes into the 3 position on the ring, the ‘Nitro’
groups direct the new groups into the 3 and 5 positions of the Benzene
ring. Basically, the Nitro groups make the ring much less reactive than
the original Benzene ring.
Mechanism
Step 1: Formation of Electrophilic by the help of Nitrating Agent. The
electrophile is the ‘Nitronium Ion’ or the ‘Nitryl Cation’, . This is
formed by reaction between the Nitric Acid and the Sulphuric Acid as follows.

Step 2: Formation of Intermediate Complex in which Electrophilic, such as


Nitronium Ion is attached with Benzene Aromatic Ring. It is slow
step or Rate determining step.

Step 3: Deprotonation in presence of Anion. Deprotonation is the removal


(transfer) of a Proton (a Hydrogen Cation, H+).

Self-Instructional
62 Material

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