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What is the proper procedure for the preparation of p-nitroaniline using aniline and nitric acid as the starting materials, and how can the purity of the final product be confirmed using various analytical techniques?

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The preparation of p-nitroaniline from aniline and nitric acid can be carried out through a nitration reaction. Here is a step-by-step procedure for this reaction:1. Safety precautions: Wear appropriate personal protective equipment  PPE  such as gloves, goggles, and a lab coat. Work in a well-ventilated area or fume hood, as the reaction involves corrosive and toxic chemicals.2. Prepare the nitrating mixture: Slowly add concentrated nitric acid  HNO3  to concentrated sulfuric acid  H2SO4  with constant stirring. The mixture should be cooled in an ice bath to maintain a low temperature  around 0-5C  to prevent the formation of undesired by-products.3. Dissolve aniline: Dissolve aniline  C6H5NH2  in a minimal amount of glacial acetic acid  CH3COOH  to form an acetanilide derivative. This step is crucial to prevent the formation of meta- and ortho-nitroaniline isomers.4. Nitration reaction: Slowly add the cold nitrating mixture to the aniline solution with constant stirring. Maintain the temperature below 10C to ensure selective para-nitration.5. Quench the reaction: After the addition is complete, slowly pour the reaction mixture into crushed ice and water to quench the reaction. The p-nitroaniline will precipitate as a solid.6. Isolation and purification: Filter the solid p-nitroaniline using vacuum filtration. Wash the solid with cold water to remove any remaining acid. Recrystallize the product from a suitable solvent  e.g., hot water or ethanol  to obtain pure p-nitroaniline crystals.7. Drying: Dry the purified p-nitroaniline crystals in a vacuum desiccator or an oven at a low temperature  40-50C .To confirm the purity of the final product, various analytical techniques can be employed:1. Melting point determination: Compare the melting point of the synthesized p-nitroaniline with the literature value  147-149C . A sharp melting point close to the literature value indicates high purity.2. Thin-layer chromatography  TLC : Perform TLC analysis to check for the presence of any impurities or unreacted starting materials. A single spot on the TLC plate indicates a pure product.3. Infrared  IR  spectroscopy: Analyze the IR spectrum of the synthesized p-nitroaniline and compare it with the reference spectrum. The presence of characteristic peaks  e.g., nitro group peak around 1530-1350 cm-1  and the absence of starting material peaks confirm the purity of the product.4. Nuclear magnetic resonance  NMR  spectroscopy: Obtain 1H-NMR and 13C-NMR spectra of the synthesized p-nitroaniline and compare them with reference spectra. The presence of characteristic signals and the absence of impurity signals confirm the purity of the product.5. Elemental analysis: Perform elemental analysis  CHN analysis  to determine the percentage of carbon, hydrogen, and nitrogen in the synthesized p-nitroaniline. Compare the obtained values with the theoretical values for p-nitroaniline to confirm the purity of the product.

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