Post-Lab Questions: 1. One method for favoring the formation of an ester is to add excess acetic acid.

Suggest another method, involving the right hand side of the equation, that will favor the formation of the ester. Acetic Acid + Isopentyl Alcohol
H+

Isopentyl Acetate + Water

A reaction can be pushed to the reactants by removing some of the product. In this case, since we are trying to form the ester, we would remove water. This could be accomplished by adding a compound like silica, which is good at absorbing water. 2. Why is it easier to remove excess acetic acid from the products than excess isopentyl alcohol? Our product, isopentyl acetate has very low solubility in water but good solubility in a solvent like diethyl ether. Isopentyl alcohol is also very soluble in diethyl ether. It would be more difficult to separate the excess isopentyl alcohol because of the similar solubility characteristics. Acetic acid is soluble in water, but it is also soluble diethyl ether. Therefore, some, but not all, excess acetic acid could be extracted with a standard separation. However, we can easily convert acetic acid into its conjugate base by adding a base like sodium bicarbonate. Sodium acetate, the conjugate base, is soluble in water but not in diethyl ether. Then, when we remove the aqueous layer, the excess acetic acid (in its conjugate base form) will be removed.

4. Which starting material is the limiting reagent in this procedure? Which reagent is used in excess? How great is the molar excess (how many times greater)? Experiment 13A: ( ( )( )( )( ) )

Experiment 13B: ( ( )( )( )( ) )

Isopentyl alcohol is the limiting reagent. Acetic acid is used in excess. On average, there was 2.71 times molar excess of acetic acid.

10. Write a mechanism for the acid-catalyzed esterification of acetic acid with isopentyl alcohol. You may need to consult the chapter on carboxylic acids in your lecture textbook.

Conclusion: During this lab, I learned the procedure to synthesize an esther from an alcohol. During the lab, we did produce a yellowish-brown liquid with the appropriate fake banana magic marker smell. During the separation process, we kept the hot plate at 180oC, as listed in the lab manual. We began the distillation process, but did not have time to complete it. After waiting over 30 minutes, it we turned up the temperature of the hot plate, but ran out of time before any liquid was distilled. Other groups had the same issues so we were no longer required to report our percent yield. Our team members working on procedure 13B were in the process of determining the boiling point of their ester when time ran out. If I attempt this procedure again, I would like to have more time. Of course, that may not be possible. I would also turn up the temperature of the hot plate more quickly.

Isopentyl Acetate Lab Organic Chemistry Jeannette Bernay

Abstract: In this experiment, we synthesized the ester isopentyl acetate by combining an excess of acetic acid and isopentyl alcohol. This reaction was catalyzed with sulfuric acid. Sodium bicarbonate was added to create an acid-base reaction with the excess acetic acid. The aqueous layer was removed. The remaining ester was then distilled.

Introduction: Esters are used in the cosmetic, pharmaceutical and food industries. Research is being conducted to determine procedures to produce high yields of various esters. For example, at the Technical University of Denmark, scientists have studied the use of Novozym 435 as a catalyst in the esterification of alcohols of different chain length with lactic acid. With the exception of 1-octanal, all alcohols tested had ester yields from 70.8% to 81.7%. By using this catalyst esters can be synthesized with both short- and long- carbon chains. These esters can then be used to produce other substances, such as cosmetics and pharmaceuticals.

Works Cited: Roenne, Torben H., Xuebing Xu, and Tianwei Tan. "Lipase-Catalyzed Esterification of Lactic Acid with Straight-Chain Alcohols." JAOCS, Journal of the American Oil Chemists Society 82.12 (2005): 881-5. ProQuest Research Library. Web. 12 Jan. 2012.