Basic Concepts in Organic Chemistry Experiment: Preparation of Aspirin
Experiment Overview
In this experiment, we will synthesize aspirin (acetylsalicylic acid), a common over-the-counter pain reliever and anti-inflammatory drug, through the esterification reaction of salicylic acid and acetic anhydride. This experiment demonstrates the fundamental concepts of organic chemistry, including functional group reactivity, reaction mechanisms, and purification techniques.
Materials and Equipment
- Salicylic acid
- Acetic anhydride
- Concentrated sulfuric acid (Note: Handle with extreme caution)
- Ethanol
- Deionized water
- Round-bottom flask
- Reflux condenser
- Heating mantle
- Thermometer
- Separatory funnel
- Vacuum filtration apparatus
- Vacuum pump
- Büchner funnel
- Filter paper
- Anhydrous sodium sulfate (drying agent)
- (Optional) Rotary evaporator
Procedure
- Prepare the Reaction Mixture: In a round-bottom flask, add 5 grams of salicylic acid and 10 mL of acetic anhydride. Carefully add 1 mL of concentrated sulfuric acid to the mixture while swirling the flask to ensure thorough mixing. (Note: Add the acid slowly and cautiously to avoid splashing.)
- Reflux the Reaction: Attach a reflux condenser to the round-bottom flask and heat the mixture under reflux for 30 minutes using a heating mantle. Monitor the internal temperature using a thermometer, aiming to maintain it between 80°C and 90°C.
- Cool the Reaction Mixture: After 30 minutes, remove the reaction flask from the heating mantle and allow it to cool to room temperature.
- Extract the Product: Transfer the cooled reaction mixture to a separatory funnel. Add 20 mL of ice-cold water (to decompose excess acetic anhydride) followed by 20 mL of ethanol and shake gently (vent frequently). The aspirin will largely remain in the organic (ethanol) layer.
- Separate the Layers: Allow the mixture in the separatory funnel to settle until two distinct layers form. Carefully drain the lower aqueous layer into a waste container, ensuring that the organic layer remains in the funnel.
- Wash the Organic Layer: Wash the organic layer with 10 mL of deionized water to remove any remaining impurities. Drain the water layer into the waste container.
- Dry the Organic Layer: Transfer the organic layer to a clean, dry round-bottom flask and add a small amount of anhydrous sodium sulfate to remove any residual water. Swirl the flask gently and allow the solid sodium sulfate to settle to the bottom.
- Filter the Organic Layer: Filter the dried organic layer through a Büchner funnel fitted with filter paper to remove the solid sodium sulfate. Collect the filtrate in a clean, dry round-bottom flask.
- Crystallize the Aspirin: Evaporate the solvent (ethanol) from the filtrate using a rotary evaporator or by placing the flask in an ice bath. As the solution cools, aspirin crystals will form.
- Collect and Purify the Aspirin Crystals: Once crystallization is complete, collect the aspirin crystals by vacuum filtration. Rinse the crystals with a small amount of ice-cold water or ethanol to remove any impurities. Allow the crystals to air dry completely.
Significance
This experiment showcases several basic concepts in organic chemistry:
- Functional Group Reactivity: The reaction between salicylic acid and acetic anhydride demonstrates the reactivity of carboxylic acids and acid anhydrides in esterification reactions.
- Reaction Mechanisms: The experiment illustrates the mechanism of an esterification reaction, which involves the nucleophilic attack of the hydroxyl group of salicylic acid on the carbonyl carbon of acetic anhydride.
- Purification Techniques: The extraction, washing, drying, and crystallization steps demonstrate essential purification techniques commonly used in organic chemistry to isolate and purify the desired product.
- Synthesis of a Common Drug: Aspirin is a widely used drug, and its synthesis in the laboratory provides a practical application of organic chemistry principles.
This experiment is a valuable learning resource for students to gain hands-on experience with organic reactions, purification techniques, and the synthesis of a real-world product. Remember to always follow proper safety procedures when handling chemicals.