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Fischer Esterification

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Fischer Esterification

By Bohlin

Abstract:

In this experiment, an unknown alcohol underwent a Fischer Esterification reaction by reacting it with acetic acid as well as sulfuric acid catalyst. The unknown product material was purified through distillation and characterized by analyzing an IR spectrum and determining the density of the product. In addition, the boiling point test was performed to test for an ester. Lastly, the starting material, an unknown alcohol, was determined after finding out the product and examining the IR spectrum for the reactant.

Procedure:

An acetate was synthesized by reacting an alcohol with acetic acid. Since the acetic acid, a carboxylic acid, is less reactive than the acetate, an ester, the sulfuric acid catalyst was used to make the reaction more favorable. Sulfuric acid easily donates a hydrogen ion to protonate the carbonyl oxygen in acetic acid, forming a stable intermediate with contributing resonance structures. The nucleophilic alcohol compound then simply attacks the electrophilic carbon in the intermediate. After, the intermediate undergoes tautomerism where a proton is shifted from the newly formed oxonium ion to the hydroxyl group, forming an activated complex. Overall, the reaction results in the removal of water and deprotonation of the complex forming an acetate.

Date Table:

|Glacial Acetic Acid |17M |0.050 moles |
|Unknown Alcohol |Isobutyl Alcohol |3.5 ml |
|Sulfuric Acid |11M |0.5 ml |
| | |

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