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chemistry

Experiment #3: The Fischer Esterification
Flavors and Fragrances
Devin Sweeney
Organic Chemistry Lab 272
Dates: February 1, 2001- Esterification
February 6, 2001- Ester Work Up
February 13, 2001- NMR, IR,
And Gas Chromatography

I. Introduction and Background
Organic compounds that are classified into the ester group are commonly
Associated with very pleasant smelling fragrances. These esters can be synthesized by combining a carboxylic acid with an alcohol while using a mineral catalyst. By causing a reaction between ethanoic acid, more commonly known as acetic acid, and 3-methyl-1-butanol or isopentyl alcohol, the ester isopentyl acetate (3-methyl-1-butyl ethanoate) is produced. Isopentyl acetate is easily recognizable by the strong, "banana," odor. This ester is used to give perfumes, foods, and beverages their fragrance and is a major component of banana oil. In order to synthesize isopentyl acetate, glacial acetic acid undergoes esterification with isopentyl alcohol.
Before the process of esterification can begin, the starting material acetic acid must be obtained. Acetic acid can either be found naturally or produced synthetically. In nature, this acid is found as a product of the oxidation of ethanol. Acetic acid is the major organic component of vinegar. If the sugars in apple cider or grape juice are allowed to ferment ethanol is formed initially, but prolonged fermentation leads to acetic acid. Acetic acid dissolves most simple organic compounds, and it has a convenient boiling point (118 C). In this experiment acetic acid is both the solvent and reactant. Using an excess of acetic acid also helps to drive the equilibrium toward the desired product (Mohrig, Hammond, Morrill, and Neckers). Once the method for producing acetic acid is known, we can add isopentyl alcohol in attempt to produce isopentyl acetate. By understanding the process involved in producing isopentyl acetate, a substantial amount of surplus c…

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