Fischer Esterification

Fischer Esterification - carboxylic acid was known to be...

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Introduction In this experiment, a Fischer esterification was performed. This can be done by refluxing a carboxylic acid (acetic acid in this case) and an alcohol (unknown) in the presence of an acid catalyst (H 2 SO 4 ). Once the organic layer was separated from the aqueous layer, a proton and carbon-13 NMR were performed on it. 1 H-NMR gives information about the hydrogen atoms in the molecule, and 13 C-NMR gives information about the carbon atoms in the molecule. These spectra can give information about the connectivity and arrangement of molecules. The NMR of the organic layer was taken to determine the ester product made and determine the identity of the unknown alcohol. Since the carboxylic acid was known to be acetic acid, the structure of the alcohol can be determined by observing what is attached to the ester oxygen. Mechanism Balanced Equation Upon viewing the 1 H-NMR, the basic structure of the ester can be determined. Since the
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Unformatted text preview: carboxylic acid was known to be acetic acid, it is known that there is only one carbon attached to the carbonyl carbon. This carbon is terminal, meaning it has 3 hydrogen atoms. It is represented by a single at about 2.0 ppm that integrates out to 3.00. The carbon atom attached to the oxygen atom of the ester is downfield, represented as a triplet that integrated out to 2.09. There is a quintet at about 1.7 ppm that integrates out to 1.33 and a quartet at about 1.5 ppm that integrates out to 2.19. These two peaks help determine what is hanging off of the ester. The structures of the ester and alcohol are shown below. The 13 C-NMR did not prove to be useful because the reaction was not run to completion, and remnants of the alcohol and carboxylic acid were present. Questions 1. 2. isoamyl alcohol: 3-methyl-1-butanol isoamyl acetate: 3-methyl-1-butylacetate 3. a. b....
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Fischer Esterification - carboxylic acid was known to be...

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