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esters

Experiment #3: The Fischer Esterification

Dates: February 1, 2001- Esterification

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 th


3. Snell, Foster Dee, ed. Snell-Ettre Encyclopedia of Industrial Chemical Analysis, v10. Interscience publishers, 1970.

g the extensive research that needs to be performed to truly understand the significance of this ester outside of the perfume and banana oil field.

. By running an infrared spectrometry (IR) important information about the particular functional groups of a compound is obtained. This allows for the naming of an unknown compound by analyzing the different functional groups that makes up the specific compound. The regions in which the functional groups appear fall between 4000-1300 cm-1 on the spectra. Since the compound synthesized was an ester, the first thing one should look for on the spectra is a strong peak between 1800-1700 cm-1. The spectra did indeed have a strong peak at 1742.7cm-1 that is the carbon-oxygen double bond known as the functional group in esters. The alkyl carbon-hydrogen, part of the compound is represented by a peak around 2900 cm-1 on the spectra. The spectra results of the isopentyl acetate produced in class proved to be very similar to those found in Sadtler.

Began by combing 16 ml of isopentyl alcohol and 22 ml of glacial acetic acid; These specific amounts were used because a limit (between 5g-10g) had been set on the amount of limiting reagent being used. In order for this reaction to take place, a catalyst was required so sulfuric acid was used. The process of esterification was started by assembling a reflux apparatus and beginning to heat this mixture at 60oC for an hour. While this mixture was heating, it changed from a foggy appearance dark yellow color almost immediately. Also, after about 8 minutes of boiling, an obvious odor of banana could be smelt. Upon removing this mixture after the hour of boiling was over, the sweet, fruity, banana smell was very strong and distinct and the solution was very dark yellow. After successful completion of forming this product, this mixture was put into a separatory funnel washed with 50 ml of distilled water and the lower aqueous layer was drained out, separating it from the upper org!

e major organic component of vinegar. If t

Some common words found in the essay are:
Discussion Initially, Background Organic, NMR NMR, IR GC, II Conclusion, Morrill Neckers, GC IR, acetic acid, isopentyl acetate, Chemical Analysis, York York, Encyclopedia Walter, isopentyl alcohol, glacial acetic acid, glacial acetic, cm-1 spectra, carboxylic acid, process esterification, form isopentyl acetate, form isopentyl, carboxylic acid alcohol, diethyl ether, combining carboxylic, combining carboxylic acid, excess acetic acid,
Approximate Word count = 1442
Approximate Pages = 6 (250 words per page double spaced)


  

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