Procedure

Into a 5 mL round-bottomed flask, isopentyl alcohol (1.2 mL), acetic acid (0.744 mL), 4 drops of concentrated sulfuric acid and 3 boiling chips were added. The solution was refluxed for 15 minute intervals for a total of 3 intervals or 45 minutes. After each interval, the organic phase was removed from the side arm of the flask and added to the solution. After refluxing, the contents of the round-bottomed flask were transferred to a centrifuge tube. The centrifuge tube was extracted with water (1 mL). This extraction process was repeated with sodium bicarbonate (1 mL) and sodium chloride (1 mL). 5 spheres of calcium chloride were added into a vial containing the organic phase. The mixture was transferred to a new vial and analyzed by infrared spectroscopy.