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Ester Synthesis Lab Report

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The goal of this experiment was to synthesize the unknown ester through Fischer Esterification. This procedure involves treating a carboxylic acid with an alcohol and a strong acid catalyst. This procedure was also catalyzed with heat at 160oC-180oC, to keep the temperature from exceeding the boiling points of the compounds in use. The acid catalyst protonated the double bonded oxygen atom to force the atom to pull two electrons away from the double bond in order to stabilize the atom’s charge. As this electron shift occurred, the alcohol attacked the carbocation that lost its double bond. The acid catalyst then deprotonates the alcohol so it could retain its neutral charge and then the acid protonates the other hydroxide group, to produce H2O which separates from the main compound to stabilize its own charge and then carbocation rearrangement occurs to form a pi bond. …show more content…

The acid catalyst then deprotonates the final hydroxide group that donated two electrons during the rearrangement in order to stabilize the compound once again, hereby ending with the synthesis of the ester with an excess of

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Lab Report 5: Acetylsalicylic Acid (Aspirin) Synthesis Name: Divya Mehta Student #: 139006548 Date Conducted: November 19th 2014 Date Submitted: November 26th 2014 Partner’s Name: Kirsten Matthews Lab Section: Wednesday 2:30 L9 IAs Name: Brittany Doerr Procedure: For the procedure, see lab manual (CH110 Lab Manual, Fall 2014) pages 96-98. Wilfrid Laurier University Chemistry Department. Fall 2014. Acetylsalicylic Acid (Aspirin) Synthesis.

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Based on the position of the charge, two or three products can be produced. After the protonation of the alcohol group on 2-methylcyclohexanol, resulting in water (good leaving group), a double bond will form, producing 3-methylcoyclohexene.

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The objective of this experiment was the synthesis of Isopentyl Acetate using an esterification reaction between acetic acid and Isopentyl Alcohol, using a strong acid as a catalyst. The product was washed, and distilled. This approach is called Fisher esterification, whereby esters are produced by refluxing a carboxylic acid and an alcohol in the presence of a concentrated acid catalyst. The ester produced had a banana smell odor. The extraction of the crude product was conducted using sodium bicarbonate followed by distillation.

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The third ester which reacted was ethyl butanoate since it was a bit more sterically hinder than the ethyl acetate because the carbonyl group was connected to a secondary carbon. Both ethyl acetate and ethyl butanoate had electronic factors of being electron donating making the carbonyls less reactive so the order depended more on the steric factor. The slowest ester to react was the ethyl benzoate because of the greater steric hindrance since the carbonyl was connected to a benzene ring which making it hard for the nucleophile to attack. The carbonyl was directly connected to a tertiary carbon, but that was also in a ring. The benzene is an electron

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In this experiment, the fundamental objective was to synthesize an ester by utilizing the Fischer esterification technique. This method included by using acetic acid and an unknown alcohol #110 as the reactants. Afterward, the reaction was processed, and the product was isolated and purified respectively by isolation and distillation. Then, IR spectroscopy was characterized the product, which demonstrated prominent peaks at 1737.54 cm-1, 1381.

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The ester studied was “3,” the acid used was 9.5 mL of “B,” and the alcohol used was 18.1 mL of “C.” A few substances were added to augment the production of the ester. Sulfuric acid (H2SO4) was added using a dropper bottle to catalyze the reaction. The desiccant in this reaction was drierite and was used to absorb the water byproduct. This prevented the ester from breaking apart into its constituents. The cold finger condenser was used to trap evaporated gas from the heated mixture, and condense it back into

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The first step is a simple acid base reaction with the carbonyl oxygen and a proton. The proton shown as a “bare” proton, but in reality, the proton would be solvated with water. After the positive charge is formed on the oxygen atom it can then be delocalized throughout the conjugated system.” When the oxygen is protonated by adding hydrochloric acid, one of the double bonds in the carbonyl group will become a lone pair and this will increase the repulsion. Then the double bond between the two central carbons is delocalized and forms between the oxygen atom and the carbon atom.

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The acid-catalysed dehydration of a secondary and primary alcohol revealed that the E1 mechanism undergoes and favors rearrangement for a more stable carbocation; this reaction favors a Zaitsev product, which attacks the most substituted beta hydrogen. The base-induced dehydration of a secondary and primary bromide undergoes an E2 mechanism and favors a Hoffman product because of the presence of a sterically bulky base, which attacks the least substituted beta hydrogen. The percent compositions obtained through Gas Chromatography revealed that these favored types of products were present in the highest

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The conjugate acid and base were obtained by adding

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