Isopentyl Acetate Synthesis

Introduction The purpose of the experiment was to synthesize and purify isopentyl acetate or banana oil. In order to perform this reaction, the mixture containing excess acetic acid and isopentyl alcohol was heated under reflux. The methods of extraction, drying, and distillation were then used to help purify the isopentyl acetate. After the completion of all these processes, we were able to determine the yield and analyze our isopentyl acetate.

Experiment Scheme1

Equation 1. Esterification of acetic acid to form isopentyl acetate. The experiment to attain isopentyl acetate contained various steps and processes. First, we assembled the reflux apparatus by using a 25-mL round-bottom flask, water-cooled condenser, and heating mantel.

The reaction the occurred in the experiment was a reaction between acetic acid and isopentyl alcohol to form isopentyl acetate and water. The esterification of acetic acid with isopentyl alcohol occurs in four steps. The first step in the reaction mechanism is the protonation of acetic acid with a proton from the concentrated sulfuric acid that was added to the reaction mixture. In the second step, acetic acid reacts with the isopentyl alcohol to form a reaction intermediate which undergoes proton transfer or rearrangement protonation. Water acts as a leaving group in the third step and is removed from the reaction intermediate. In the fourth step, the molecule undergoes deprotonation with the help of the concentrated sulfuric acid to form isopentyl acetate. The reaction that was carried out in the experiment was a reversible reaction. In order to obtain as much isopentyl acetate as possible, Le Chatelier’s principle was used to ensure that we were able to collect a sufficient amount of isopentyl acetate. Le Chatelier’s principle says that if you disturb a system in equilibrium the equilibrium will shift in order to account for the disturbance. In our experiment, we used excess acetic acid. The presence of excess acetic acid caused the reaction to shift toward the opposite side of the reaction. This resulted in the production of isopentyl acetate being favored, which allowed

In our experiment, we were able to synthesize isopentyl acetate by heating a reaction mixture of isopentyl alcohol with excess acetic acid. We were then able to purify the isopentyl alcohol by using the methods of extraction, drying, and distillation. Our synthesis and purification of isopentyl acetate was fairly successful in allowing us to obtain and analyze banana oil.

Questions

1. In addition to using excess acetic acid to form the ester, the reaction can also be influenced by removing water from the reaction mixture. Based on Le Chatelier’s principle, removing a reagent from the right side of the equation will shift the reaction to the right. Disturbing the reaction equilibrium by removing water from the mixture will cause the reaction to shift to the right and establish a new equilibrium. The new equilibrium that is established after the removal of water favors the formation of the ester.

2. The limiting reagent in the procedure is isopentyl alcohol. The reagent that is used in excess is acetic acid due to the inexpensive nature of this chemical. The amount of the excess reagent that was used in the procedure was 2.6 time greater than the amount of the limiting reagent that was used in the