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chemistry

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


Initially, the only thing given concerning the synthesis of the product was the structure and it's respective common name. With this limited amount of information one has to come up with the reagents needed to form isopentyl acetate using the esterification process. Using basic knowledge about how esters are formed from combining a carboxylic acid and an alcohol, one can determine that isopentyl alcohol and glacial acetic acid are the reagents that would form isopentyl acetate via esterification.

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!

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anic layer. This just described was necessary in order to remove the excess acid from the product. Then sodium bicarbonate was used in the same way that the water was used to separate further all the impurities that my compound was likely to have picked up. These steps were repeated until the layer that was being drained out could turn litmus paper blue. After this "work-up" part of the procedure, anhydrous calcium chloride was added as a drying agent and let to sit for 10-15 minutes. Next decant the product from the calcium chloride. Now, the only thing left to do is to remove imp

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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