Orgo 2 Post Lab 5

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Feb 20, 2024

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Running head: SYNTHESIS OF ACETYLSALICYCLIC ACID 1 Synthesis of Acetylsalicylic Acid Anjenelle Fernandez, Steve Smith University of South Florida CHM 2211L: Organic Chemistry II Lab Isaiah Nelson
SYNTHESIS OF ACETYLSALICYLIC ACID 2 Synthesis of Acetylsalicylic Acid Aspirin, also referred to as Acetylsalicylic Acid, is a common medication used to relieve pain, fever, and inflammation (Wildegirma, 2023). It consists of a carboxylic acid functional group and an acetyl group attached to an aromatic ring (Wildegirma, 2023). It is prepared through esterification with acetic anhydride and salicylic acid. Esters are prepared through reacting to an alcohol with a carboxylic acid catalyst and within this experiment it is an acid anhydride with salicylic acid. Within this experiment Fischer esterification is used which is with a carboxylic acid with an alcohol using a strong acid catalyst, such as sulfuric acid (Wildegrima, 2023). Esterification reactions require the acid catalyst, an acid with a carboxyl group, elevated temperature, and removal of water (Clark, 2023). The process of esterification is used in forming aspirin, but also in soap making and flavoring food and beverages (Wildegirma, 2023). IR and NMR Spectra can be utilized to identify if the aspirin has been synthesized through the IR spectra showing a broad peak near or above 3300 to represent the alcohol and a peak representing the carbonyl stretch around 1650-1800 representing the carbonyl stretch within the carboxylic acid. Figure 1: Detailed mechanism for Synthesis of Acetylsalicylic acid
SYNTHESIS OF ACETYLSALICYLIC ACID 3 Figure 2: Possible side reaction Figure 3: Possible side reaction Figure 4: Possible side reaction
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SYNTHESIS OF ACETYLSALICYLIC ACID 4 Experiment Procedures Pre-Reaction: Conical Vial + 138 mg salicylic acid + boiling chip + 1 drop H 3 PO 4 + 0.3 mL acetic anhydride + mix gently + spot initial TLC + heat water in beaker to 90°C +suspend vial in bath + heat for 5 minutes +run TLC, determine R f Analysis Reaction in hot water Reaction Workup + cautiously add 0.2 mL + add slowly to avoid side reaction + add another 0.3 mL water + remove from heat, cool to room temp +see crystallization Crystallization + if no crystal, cool to 0°C for recrystallization of use seed crystallization + remove solvent using pipet + use vacuum filtration if too small +place crystals into filter paper and dry
SYNTHESIS OF ACETYLSALICYLIC ACID 5 Chemicals Salicylic Acid Formula: C 7 H 6 O 3 Molar mass: 138.12 g/mol Melting point: 159°C Boiling point: 211°C IUPAC: 2-hydroxybenzoic acid Hazards: Causes serious eye irritation Harmful if swallowed Acetic Anhydride Formula: C 4 H 6 O 3 Molar mass: 102.09 g/mol Melting point: -73.1°C Boiling point: 139.5 °C IUPAC: Acetic anhydride Hazards: Flammable Corrosive Harmful if swallowed or inhaled + obtain mass + calculate % yield + obtain melting point + obtain IR spectrum
SYNTHESIS OF ACETYLSALICYLIC ACID 6 Results No product was obtained, no crystals were formed R f of Salicylic Acid: 2.5/4.0 cm = 0.625 R f of Acetylsalicylic Acid: 1.8/4.0 cm = 0.450 Percent Yield: actual yield/ theoretical yield x 100 (0.0g)/(0. 0.180 g) x 100 = 0 Rate of reaction: fast Acetylsalicyclic Acid Formula: C 9 H 8 O 4 Molar mass: 180.16 g/mol Melting point: 128-137 °C Boiling point: 140°C IUPAC: 2-acetyloxybenzoic acid Hazards: Causes serious eye irritation Harmful if swallowed Causes damage to organs
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SYNTHESIS OF ACETYLSALICYLIC ACID 7 Figure 5: 1 H NMR Graph Discussion There was no melting obtained due to the product not being formed. The 1H NMR does not indicate that the product has been synthesized. The TLC within the experiment indicates that some reactants formed a product. Issues with yield may be due to the chemicals being added in an incorrect order or amounts. There was no IR spectrum obtained due to the lack of crystal formation. The proper IR could be useful for identifying if any unwanted side reaction occurred through showing the improper functional groups forming. Conclusion In conclusion, the data of this does not connect to theory as the product was not synthesized. The aim of the experiment, synthesizing aspirin from salicylic acid and acetic anhydride, was not met. However, the technique of Fischer esterification can be utilized in other
SYNTHESIS OF ACETYLSALICYLIC ACID 8 experiments to produce a variety of different esters. In addition to this IR spectroscopy can be used to identify the functional groups of an unknown molecule and 1H NMR can be utilized to infer the connectivity of a molecule and identify its structure.
SYNTHESIS OF ACETYLSALICYLIC ACID 9 References Clark, J. (2023, January 23). Making esters from alcohols . Chemistry LibreTexts. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Or ganic_Chemistry)/Esters/Synthesis_of_Esters/Making_Esters_From_Alcohols Farmer, S. (2023, January 23). Fischer esterification . Chemistry LibreTexts. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Or ganic_Chemistry)/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/ Fischer_Esterification National Center for Biotechnology Information (2023). PubChem Compound Summary for CID 7918, Acetic Anhydride. Retrieved July 20, 2023 from https://pubchem.ncbi.nlm.nih.gov/compound/Acetic-Anhydride. National Center for Biotechnology Information (2023). PubChem Compound Summary for CID 2244, Aspirin. Retrieved July 20, 2023 from https://pubchem.ncbi.nlm.nih.gov/compound/Aspirin. National Center for Biotechnology Information (2023). PubChem Compound Summary for CID 338, Salicylic Acid. Retrieved July 20, 2023 from https://pubchem.ncbi.nlm.nih.gov/compound/Salicylic-Acid. Weldegirma,S. (2023).  Experimental organic chemistry laboratory manual: CHM 22110L and CHM2211L . University of South Florida.
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