Chm237

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Arizona State University *

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237

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Chemistry

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Feb 20, 2024

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1 Acetaminophen Synthesis from P-Aminophenol Tempe PSH 334 Abstract The primary goal of this experiment was to synthesize acetaminophen by reacting p-aminophenol and acetic anhydride in a laboratory setting using several synthesis methods. The primary steps of the experiment included combining the reactants, heating via reflux, crystallizing and recrystallizing the purified result. A recrystallized acetaminophen sample

2 showed a shorter melting point range, indicating higher purity and a percentage yield indicating the procedure was successful. These findings demonstrate the power of organic synthesis methods, highlight the value of purification procedures, and offer valuable insights into organic chemistry. Introduction An over-the-counter pain medication, our primary goal in this project is to create acetaminophen. This synthesis produces acetaminophen via a chemical interaction between p-aminophenol and acetic anhydride (Shen et al., 2023). In addition to this general objective, we seek to acquire practical knowledge of organic synthesis methods and insight into the underlying principles driving chemical reactions within organic chemistry. In organic chemistry, complex molecules are built from simpler starting elements, accomplished by chemical synthesis (Romeo et al., 2023). Breaking and forming covalent bonds in a series of reactions is a common step in the process, which leads to the synthesis of new and more complex structures (Das & Park, 2023). However, it is essential to note that complex syntheses can include many steps and require a great deal of time and effort, as shown by synthesizing molecules like vitamin B12. A theoretical understanding of chemical reactions and the importance of heat in their progression is crucial to the success of our synthesis. Reflux, a type of controlled heating, will be crucial to the success of this experiment by expediting the reaction. Activation energy is needed because of the delicate balancing act of breaking and establishing reactant bonds. In the following sections of this report, we will go into the essential part of the experiment, explaining in detail how various methods were used to collect data (including recrystallization, melting

3 point analysis, and infrared spectroscopy). This experiment makes predictions of the results of these observations and applying theoretical knowledge in the real world is possible. Experimental Approximately 150 mg of p-aminophenol, but the exact value was 0.156 g was indicated to pour into a 5 ml reaction vial. 0.5 ml of distilled water and 0.3 ml of acetic anhydride was added to the vital as well. A magnetic spin vane was placed in the vial and a condenser was attached to the vial. After conducting the steps, the reaction was heated in an aluminum block until reflux and stirred using a magnetic stirrer. Once dissolved a timer was set for twenty minutes. To isolate the product the vial was removed from the heat and it was cooled by room temperature. Once it was cool, the air condenser was removed. After removing the air condenser forceps were used to remove the spin vane and it was rinsed with three drops of distilled water into the reaction vital. While rinsing the spin vane crystals started to form and the vial was placed in an ice bath for immediate crystals form. . Approximately, after 1-2 minutes the vial was removed and quickly filtered to isolate the product. 0.5 ml of distilled water was used to rinse and wash the crystals on the funnel. For fifteen minutes the crystals were dried with air drawn through a filter paper. After fifteen minutes the crystals were weighed and crushed for the recrystallization process. A small portion was put into a melting point capillary. To continue, the crude product was placed into a test tube and the test tube was placed in a beaker with water in the hotplate. Two ml of methanol and two ml of water were used as the 50:50 equation indicated and was added to the test tube. After being boiled and cooled at room temperature crystals started to form. Test tube was placed into an ice bath for completion of

4 crystals. A previous step conducted above was completed again, crystals were removed and quickly filtered using a filter paper to purify the product on the funnel. After performing the reaction, isolating the product and purifying the product the last step was to characterize. To characterize the product a melting point range was used. Using three melting point capillary tubes: p-aminophenol, the crude, and the recrystallized product. A small portion of the pure product was used to create the final acetaminophen IR Spectrum. Results In the first equation, the moles of P-aminophenol were determined by dividing the experiment amount conducted in the lab (0.156 g) by the molecular weight ( 109.13 g/mol). In the second equation, the moles of acetic anhydride were determined by the experimental volume (0.3 ml) multiplied by the density value (1.08 g/mol) and then divided by the molecular weight ( 102.09 g/mol). P-aminophenol was identified as the limiting reagent. Moles of para-aminophenol = Weight of para-aminophenol (g) = 0.156 g = 0.00142949 mol Molecular Weight (g/mol) 109.13 (g/mol) Moles of acetic anhydride = Weight of acetic anhydride (g) = (1.08 g/mol x 0.3 ml) = Molecular Weight (g/mol) 102.09 (g/mol) 0.00317367 mol Acetic anhydride density = 1.08 g/ml Limiting Reagent for the Reaction: 0.00142949 mol Once crystallization was conducted, the moles of crude product were calculated by the weight of the experimental value (0.046 g) divided by acetaminophen weight (109.13 g.mol).

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