Nitration of acetanilide

synthesis of p nitroaniline from aniline lab report

This nitronium ion was formed by the reaction of sulfuric and nitric acids. Big hi to all of you! Dhirendra Kumar Tarai. Wash it thoroughly with water. To avoid this, the addition of HNO3 acid should be done very slowly, dropwisely.

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Theory of preparation of p-nitroacetanilide from acetanilide

Step 2: Preparation of p—Nitroaniline from p-Nitroacetanilide. The melting point is determined to characterize the product. Discussion Through the use of electrophilic aromatic substitution, acetanilide is nitrated to nitroacetanilide. Add a cold mixture of concentrated nitric acid 11 ml and concentrated sulphuric acid 7 ml drop wise with constant stirring to a reaction mixture while maintaining the temperature below 5 oC. Therefore the mixture would get too hot exceeding the temperature range suitable for the nitration. Dhirendra Kumar Tarai. Also the addition of nitric acid is exothermic. Conclusion The initial compounds used were known. Trust me I know the feeling of surfing around the net for ages and getting nothing in return! Also there can be some experimental errors occurred during the experiment such as not controlling the exact temperatures mentioned for the reactions. Wash it thoroughly with water. Note: o-Nitroacetanilide remains in the filtrate due to its high solubility in water. The beaker was rinsed with 10mL of water containing few fragments of ice and the solution was added to the main bulk of the product.

As the colour of the product was white, it should be Para nitroacetanilide. Therefore Ortho and Para positions are more resonance stabilized than the Meta. Shah, Nirav Prakashan, Page no. Posted by.

nitration of acetanilide to p-nitroacetanilide mechanism

Step 2: Preparation of p—Nitroaniline from p-Nitroacetanilide. There are several key steps involved in the nitration.

Mechanism of acetanilide

This is due to the resonance delocalizing the benzene ring by nitrogen lone pair. Discussion Through the use of electrophilic aromatic substitution, acetanilide is nitrated to nitroacetanilide. Glacial acetic acid is used because it is a polar solvent capable of dissolving acetanilide and the acetate ion is a poor nucleophile, so no substitution is possible. Baldania and Dimal A. Mixture is useful to obtain the active nitronium ion. Some impurities might be Ortho and Meta directing substances. The first step of the reaction involved in the donation of an electron pair by the acetanilide to the eletrophile, the nitronium ion. Theoretical melting point of the Para nitroacetanilide is found to be C. Step 2: Preparation of p—Nitroaniline from p-Nitroacetanilide. Add dry acetanilide 25 g to glacial acetic acid 25 ml in a beaker and then introduce concentrated sulphuric acid 50 ml slowly with constant stirring to obtain clear solution. Trust me I know the feeling of surfing around the net for ages and getting nothing in return! Theory Acetanilide displays moderately reactivity in electrophilic aromatic substitution.

Principally, acetanilide gives Ortho and Para mono nitroacetanilides. The beaker was rinsed with 10mL of water containing few fragments of ice and the solution was added to the main bulk of the product.

Nitration of acetanilide

Filter it on suction, wash with cold water till free from acid and recrystallize the pale yellow product from ethanol to get colourless crystalline solid, m. There are several key steps involved in the nitration. In the nitration, nitronium ion acts as the electrophile that involves the attack of the electron-rich Benzene ring. Basically the whole mechanism undergoes as below; Benzene is shown here instead of acetanilide Image via en. H2SO4 was added to the mixture. Acetanilide undergoes ready nitration giving mainly the colourless P-nitroacetanilide, mixed with much smaller proportion of the yellow colour O-nitroacetanilide. Dhirendra Kumar Tarai. To avoid this, the addition of HNO3 acid should be done very slowly, dropwisely. Also the addition of nitric acid is exothermic. Hannaford, Peter W. Basically it can be carried out by a mixture of concentrated nitric acid and sulphuric acid.
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Nitration of Acetanilide