Introductions:
The purpose of this experiment is to synthesize acetaminophen and esters in order to apply the process of retrosynthetic analysis to determine the unknown alcohols used to produce the esters. Acetaminophen, a popular active ingredient in many over-the-counter drugs, is used as a pain reliever and a fever reducer. It is synthesized from the reaction between a carboxylic acid and an amine; thus, acetaminophen contains hydroxyl and amide functional groups.1
C6H7NO + C4H6O3 C8H9NO2 + C2H4O2
This reaction is commonly known as a condensation reaction. A condensation reaction is a chemical reaction where two reactants form a larger molecule while simultaneously creating a smaller molecule, usually water. This reaction is used as a …show more content…
Similar to the unique emission spectrum of different chemical elements, different esters release distinct fragrances. They are responsible for many odors such as those found in apples, bananas, strawberries, jasmine, and roses. The saturation of the ester along with its molecular weight determine the strength of the odor emitted. 3
Procedure:
First, 1.005 g of 4-aminophenol was placed in a test tube, followed by 3.1 mL of water and 1.25 mL of acetic anhydride. The mixture in the test tube was stirred for five minutes and allowed to cool to room temperature. Then, the test tube was placed into an ice bath for fifteen minutes. The precipitate formed was then filtered using vacuum filtration. Once the filtration process was completed, we measured the powdery solid using constant weighing to obtain the dry yield of the product formed. The acetaminophen synthesized was used to perform cerium and universal indicator tests. These tests were carried out by using a blank (distilled water), an aqueous solution of 4-aminophenol, and an aqueous solution of acetaminophen. 0.5 mL of cerium was added to each of the test tubes containing the blank and the solutions. To perform the universal indicator test, 3-5 drops of the universal indicator was added to test tubes containing the blank and other solutions without cerium …show more content…
The first being that sulfuric acid acts as a catalyst that helps speed up esterification at room temperature. The second reason being that sulfuric acid is a dehydrating agent. Since water is a product in esterification, sulfuric acid will force the equilibrium to the right, resulting in a higher yield of the ester. To determine the unknown alcohols used in producing the esters, retrosynthetic analysis was performed by working backwards and visualizing the bonds that were formed in order to create that ester.
There were several possibilities for error that accounted for our low percent yield (70.7%) of acetaminophen. When transferring the reactants in the test tube to the Büchner filtration apparatus, some of the precipitate remained in the test tube and on the stirring rod. Also, when we took the filtered product out of the vacuum funnel, more precipitate was lost. During filtration, we did not sufficiently rinse the precipitate with distilled water to wash off the excess acetic acid. This affected our universal indicator test, showing the acetaminophen as acidic instead of
The purpose of this experiment is to synthesize acetaminophen and esters in order to apply the process of retrosynthetic analysis to determine the unknown alcohols used to produce the esters. Acetaminophen, a popular active ingredient in many over-the-counter drugs, is used as a pain reliever and a fever reducer. It is synthesized from the reaction between a carboxylic acid and an amine; thus, acetaminophen contains hydroxyl and amide functional groups.1
C6H7NO + C4H6O3 C8H9NO2 + C2H4O2
This reaction is commonly known as a condensation reaction. A condensation reaction is a chemical reaction where two reactants form a larger molecule while simultaneously creating a smaller molecule, usually water. This reaction is used as a …show more content…
Similar to the unique emission spectrum of different chemical elements, different esters release distinct fragrances. They are responsible for many odors such as those found in apples, bananas, strawberries, jasmine, and roses. The saturation of the ester along with its molecular weight determine the strength of the odor emitted. 3
Procedure:
First, 1.005 g of 4-aminophenol was placed in a test tube, followed by 3.1 mL of water and 1.25 mL of acetic anhydride. The mixture in the test tube was stirred for five minutes and allowed to cool to room temperature. Then, the test tube was placed into an ice bath for fifteen minutes. The precipitate formed was then filtered using vacuum filtration. Once the filtration process was completed, we measured the powdery solid using constant weighing to obtain the dry yield of the product formed. The acetaminophen synthesized was used to perform cerium and universal indicator tests. These tests were carried out by using a blank (distilled water), an aqueous solution of 4-aminophenol, and an aqueous solution of acetaminophen. 0.5 mL of cerium was added to each of the test tubes containing the blank and the solutions. To perform the universal indicator test, 3-5 drops of the universal indicator was added to test tubes containing the blank and other solutions without cerium …show more content…
The first being that sulfuric acid acts as a catalyst that helps speed up esterification at room temperature. The second reason being that sulfuric acid is a dehydrating agent. Since water is a product in esterification, sulfuric acid will force the equilibrium to the right, resulting in a higher yield of the ester. To determine the unknown alcohols used in producing the esters, retrosynthetic analysis was performed by working backwards and visualizing the bonds that were formed in order to create that ester.
There were several possibilities for error that accounted for our low percent yield (70.7%) of acetaminophen. When transferring the reactants in the test tube to the Büchner filtration apparatus, some of the precipitate remained in the test tube and on the stirring rod. Also, when we took the filtered product out of the vacuum funnel, more precipitate was lost. During filtration, we did not sufficiently rinse the precipitate with distilled water to wash off the excess acetic acid. This affected our universal indicator test, showing the acetaminophen as acidic instead of