Nitration of Acetanilide | Organic Chemistry Experiment | DU MSc Chemistry Lab

The nitration of acetanilide experiment performed in the Department of Chemistry at Delhi University typically involves introducing a nitro group (-NO₂) to the aromatic ring of acetanilide via electrophilic substitution. The process utilizes a mixture of concentrated nitric acid (HNO₃) and concentrated sulfuric acid (H₂SO₄) to generate the nitronium ion (NO₂⁺), which acts as the electrophile.
Procedure Overview:
Acetanilide is first dissolved in glacial acetic acid or concentrated sulfuric acid to activate the aromatic ring.
A nitrating mixture of sulfuric acid and nitric acid is prepared, and it is added dropwise to the acetanilide solution with stirring to ensure controlled reaction conditions.
The mixture is kept at a low temperature, typically around 0-5°C, to prevent over-nitration.
After complete addition, the reaction mixture is allowed to warm to room temperature and stirred for a specified time.
The reaction is quenched by pouring the mixture into ice-cold water to precipitate the product.
The crude product, p-nitroacetanilide (predominantly), is collected by filtration, washed, and recrystallized from ethanol or water-ethanol mixture to obtain pure crystals.
The final product is characterized using melting point determination and possibly thin-layer chromatography (TLC) or infrared spectroscopy (IR).
The primary product is usually p-nitroacetanilide, with some formation of the ortho isomer depending on reaction conditions. This experiment is a classic example of aromatic nitration and demonstrates key concepts such as electrophilic aromatic substitution, regioselectivity, and recrystallization for purification.
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