Christine Chua, Danielle Sy 9C

September 11, 2013 Sharlene Joy D. Nikita

Synthesis of Isoamyl Acetate for Air Freshener Application Objective The objective of this experiment was to synthesize Isoamyl Acetate through an acidcatalyzed esterification of isoamyl alcohol with acetic acid, and then use it as an air freshener. This experiment is significant because it highlighted the pleasant odor that esters have by formulating an air freshener with the synthesized Isoamyl Acetate. Introduction Elements that chemically bond together are called compounds. There are a wide variety of organic compounds that are present in environment. These organic compounds may be classified depending on their structure, composition and present functional group. (1) Ester is one of the many classes of compounds that can be found in nature. Most of the compounds under this class have a pleasant smell. In fact, Esters are responsible for the scent that some flowers and fruits emit. Some esters may also not be present in fruits and plants, but may have the same scent as a fruit or plant. (2) An example of that ester is Isoamyl acetate, which has the scent of the banana, but isnt naturally present in bananas. In fact, pure Isoamyl acetate is referred to as Banana oil and is used in various products like perfume, chewing gum, and nail polish remover. (3) It may also be used in air fresheners. In this experiment, Isoamyl acetate was be synthesized and used to formulate a banana-scented air freshener. The reaction mechanism is illustrated below.

(4)

Results and Discussion When the mixture of 15 mL of isoamyl alcohol, 12 mL of glacial acetic acid, and 4 mL of concentrated sulfuric acid was refluxed, 13.1 mL or 10.61 g of isoamyl acetate was produced. That means that the percent yield is 59.14%. H2SO4 Chemical equation: C5H12O + C2H4O2 Limiting reactant: Isoamyl alcohol (C5H12O) Theoretical yield: C7H14O2 + H2O

The density of the product was determined by getting the mass of 1 mL. The density of the synthesized isoamyl acetate is 0.81 g/mL. That is 0.066 g/mL less than the density of pure isoamyl acetate. The percent error is [(0.066/0.876)x100] = 7.5%. The density was also used to get the mass of the product by multiply it with the volume of the product, which is 13.1 mL. The mass of the synthesized isoamyl acetate is 10.61 g. The synthesized isoamyl acetate was also tested with through the hydroxamic acid test to confirm its identity as an ester. It yielded a positive result in the hydroxamic acid test since there was a red-violet octahedral complex that formed when drops of 2% Ferric Chloride were added to the solution. In the final part of the experiment, gelatin was prepared then around 5 mL of isoamyl acetate was added to make a banana-scented air freshener.

Answer to the Pre-lab questions 1. Reaction mechanism with sulphated zirconia (5)

Reaction mechanism with another acid catalyst:

2.

The reaction of benzyl alcohol with acetic, with sulphated zirconia as a catalyst, is an SN1 reaction. A carbocation was formed when the sulphated zirconia bonded with acetic acid because the double bond of Oxygen with Carbon was broken. After that, benzyl alcohol attacked the carbocation. The hydrogen from the hydroxyl group of benzyl alcohol

would leave and protonate the hydroxyl group of the acetic acid, making it a good leaving group. The end product is benzyl acetate. The reaction of benzyl alcohol and acetic acid, with an acid catalyst like concentrated sulfuric acid, is an SN2 reaction with backside attack. The benzyl alcohol, as the nucleophile, attacks the acetic acid opposite the leaving group, which is H2O. Also, no carbocation was formed and the attack of the nucleophile happened simultaneously with the departure of the leaving group. 3. The hydroxamic acid test was used to confirm the identity of the product because esters yield a positive test in the hydroxamic acid test. The formation of a red-violet octahedral complex constitutes a positive test. The reaction of the hydroxamic acid reagent with an ester is illustrated below. 4. The chromic acid test can be performed to check if theres unreacted alcohol left in the product because benzyl alcohol is a primary alcohol. Therefore, benzyl alcohol would be oxidized into an aldehyde when subjected to this test. In this test, if there is still benzyl alcohol in the product, the test would yield a positive result. The formation of a green precipitate constitutes the positive test.

References [1] Grossmont College [Internet]. [cited 14 September 2013]. Available from: http://www.grossmont.edu/martinlarter/Chemistry%20231/Reference/ClassesCmpds %5B1%5D.pdf [2] Boch R; Shearer DA, Stone BC (September 8, 1962). "Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee.". Nature (England: Nature Publishing Group) 195: 101820. [3] Blog Critics [Internet]. [cited http://blogcritics.org/what-is-banana-oil/ 14 September 2013]. Available from:

[4] Helsinki.fi [Internet]. [cited 14 September 2013]. Available from: http://www.helsinki.fi/kemia/opettaja/aineistot/hyonteistenkemiaa/english/isopentyl%20aceta te_webpage.htm [5] Niscair Online Periodical Repository [Internet]. [cited 15 September 2013]. Available from: http://nopr.niscair.res.in/bitstream/123456789/7097/1/IJCT%2013(6)%20605-613.pdf