Synthesis of Isopentyl Acetate (Banana Oil)

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Amanda Luna Lab Partner: Irina Lev Experiment #9: Synthesis of Isopentyl Acetate (Banana Oil) Date Experiment Performed: March 28, 2012 Date Experiment Completed: April 11, 2012 Abstract: In this experiment was to synthesize isopentyl acetate (banana oil) by combining isopentyl alcohol and acetic acid and distilling it with a reflux apparatus. We also add sulfuric acid to catalyze the reaction. This allows esterification and ultimately the synthesis of isopentyl acetate. As usual we used a separatory funnel to separate the aqueous solution from organic solution in the workup section. We obtained 0.70g or product, which corresponded to a percent yield of 32.0%. TLC Plate analysis also confirmed identity. Purpose: The purpose of this experiment was to synthesize isopentyl acetate (banana oil) from isopentyl alcohol and acetic acid and confirm its identity via TLC. Overall Reaction: Reaction Mechanism: Chemicals used and their Physical Characteristics: Compounds MW (g/mol) Melting Point (˚C) Boiling Point (˚C) Density (g/mL) Glacial Acetic Acid 60.05 16-17 117.9 1.049 Isopentyl Alcohol 88.15 -117.2 130.0 0.809 Sulfuric Acid 98.08 10 337 1.84 Isopentyl Acetate 130.19 -78 130.19 0.87 Procedure: 1) Pour 16ml of isopentyl alcohol and 22ml of glacial acetic acid into 100 ml BRF 2) Swirling, add 1.0 ml of concentrated sulfuric acid to contents of the flask. 3) Add boiling stones 4) Assemble a reflux apparatus and heat the reaction mixture at reflux for 1 . 5) Remove the heat source and let it come to RT. 6) Pour the cooled mixture into a separatory funnel and carefully add 50ml of cold distilled water. Rinse the reaction flask with 5-10ml of cold water and also add this rinse to the separatory funnel. Stopper the

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