Fischer Esterification - Fischer Esterification Raymond...

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Fischer Esterification Raymond Oldham, Michael Lester, Audrey Paulzak CH-238, QZ
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Introduction Esters are a common derivative of carboxylic acids, and they contribute the chemical structure for the flavor and smell of various fruits and flowers. Esters are produced in the industrial sector as solvents, plasticizers, and starting materials for polymers, and are commonly used in perfumes and foods to add flavor and aroma. This experiment demonstrates a common way to synthesize esters. It was discovered by Nobel laureate Emil Fischer in 1902. Basically, the ester is formed through condensation of a carboxylic acid and a primary alcohol. Fischer ester synthesis is quite famously an equilibrium reaction, and more product can easily be made by added concentrations of reactants or removing product. In this experiment, our alcohol is unknown, and will be determined by the analysis of an H-NMR and C-NMR spectrum. Mechanism
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C H 3 OH O + C H 3 C H 3 OH H + C H 3 OH O + H + C H 3 C H 3 OH O H O + O H CH 3 CH 3 C H 3 H O H O O H CH 3 CH 3 C H 3 H + O H 2 + O O H CH 3 CH 3 C H 3 O O + CH 3 CH 3 C H 3 H O O CH 3 CH 3 C H 3 Table of Reagents Molecular Weight (g/ mol) BP (ºC) Density (g/mL) Acetic Acid 60.05 118 1.05 Sulfuric Acid 98.08 290 1.84 Isoamyl alcohol 88.15 130 0.81 Isoamyl acetate 130.19 142 0.88 Sodium bicarbonate 84.007 (mp) 50 2.16 Sodium sulfate 142.04 884 2.68 Procedure An empty conical vial was weighed, then put 0.7mL of isoamyl alcohol in the vial, and it was weighed again. The weight of the isoamyl alcohol alone was
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found by subtracted the final weight minus the initial weight of the empty vial. 0.517 grams of isoamyl alcohol, total, was used in the experiment.1.387 mL of glacial acetic acid was added to the mixture using a pipette, and then 3 drops of concentrated sulfuric acid were added, alone with a boiling chip. The entire mixture was heated with a sand bath and allowed to reflux with
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Fischer Esterification - Fischer Esterification Raymond...

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