Phenacetin Synthesis

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The main objective of this experiment was the formation of phenacetin from the synthesis of acetaminophen. This was done through a chemical reaction known as the Williamson ether synthesis using techniques of refluxing, vacuum filtration and recrystallization incorporating a mixed solvent system. A further objective of this experiment was to study the formation of the product (phenacetin). Such validation was completed by using techniques for determining the melting point, calculating percent yield, and IR (infrared spectroscopy) of the resultant product.
Our reaction yielded 3.696% of phenacetin product. Hence, the formation of phenacetin via acetaminophen synthesis was not a success. In addition, the poor amount of product formed was not white colored crystals, instead the crystals were of black appearance. A main reason to suggest for the unsuccessful completion of phenacetin could be due to the usage of 2 mL 2.5M sodium hydroxide solution (NaOH)/H2O, instead of the recommended ethanolic sodium hydroxide solution, which was mainly recommended because of the stability and
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The results were an indicative for expected IR spectrum of pure phenacetin. The IR spectrum showed peaks at (3281.67 cm-1) which indicate the presence of the N=H stretch, (3131.40 cm-1 and 3073.97 cm-1) representing the Sp2 C-H stretches, (2982.26 cm-1, 2927.60 cm-1 and 2885.53 cm-1) expressing the Sp3 C-H stretches, also (1656.82 cm-1) indicating the C=O amide stretch, and finally a wavelength at (1603.51 cm-1) representing the aromatic C=C stretch of the phenacetin molecule, respectively. Such IR spectrum results from phenacetin in comparison with an acetaminophen IR spectrum clearly showed the elimination of the hydroxide (OH) bond present at the acetaminophen molecular structure, which resulted in the IR spectrum not indicating the presence of a strong and broad (alcohol-phenol) band at about 3500 cm-1

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