ABSTRACT:
The objective of this lab is to synthesize acetaminophen from p-aminophenol. The techniques used to do so, consist of: reflux with heat to allow reaction to occur at a reasonable time period, extraction and filtration to isolate the desired product, and characterization of the product by analyzing IR spectras and melting points. Acetaminophen considered synthesized, primarily due to the IR spectrum exhibiting all the bond vibrations is the amide group. The percent yield of 124.6% imply that there was a mechanical error that occurred, thus, also tampering with the progression of the chemical reaction. The wide melting point range of 165 C-169 C denote the impurity of the acetaminophen product.
INTRODUCTION
Chemical synthesis is an imperative technique most relevant to organic chemists. Synthesis employs a succession of chemical reactions by using pre-existing structures to make new and functional ones. A combination of lab techniques could be developed in order to synthesize and attain the desired product. This particular experiment calls for the use for reflux, extraction, recrystallization, infrared spectroscopy, and melting point analysis. The overall objective of this lab is to utilize these steps to synthesize acetaminophen from p-aminophenol and characterize it .
To synthesize acetaminophen, calls for the following chemical reaction:
Equation 1
P-aminophenol is the reactant and acetic anhydride is added
The goal of this experiment was to find out active chemical components in Anacin and Tylenol, using Thin Layer Chromatography technique. This technique uses the difference in the intermolecular forcer and polarity to separate mixtures. Comparing Rf values were then used to determine the active chemical components in the two analgesics. The overall result was that Acetaminophen exists in Tylenol and Acetylsalicylic Acid exists in Anacin.
Therefore, the experimental yield is larger than theoretical yield. This indicates an error in how the result was produced, this could have been caused by a number of different factors. The first possible reason for this error could be a result of the drying process of the amino group. The product was left out for several minutes, however despite this the product was still wet after the drying process over should have been complete, thus increasing the mass of our product and therefor increasing the percent yield. Another possible factor in this over calculation is an excess of 4-aminophenol, which was 1.008g instead of 1 gram. Additionally, a number of errors could have been the result of time management, which in the future will need to improve. In the process of cooling reactants (4-aminophenol and acetic acid) in ice water, time could have been used more effectively in other parts of the experiment. This could have been a major factor in why 3 hours were used to complete the lab. Despite these potential errors we found that both acetaminophen and 4-aminophenol were alcohols as they produced a color change in the Cerium Test. This means that both these compounds have a hydroxyl group which coincides with the resulting chemical structure record on our green sheet. Using the Universal Indicator Test the pH of 4-aminophenol was found to be slightly basic whereas the acetaminophen was acidic. These
Acetic Anhydride and p-Aminophenol were heated in a vial attached to an air condenser to synthesize crude acetaminophen, resulting in 0.097 grams (47.48% yield). The crude acetaminophen was then recrystallized in a solvent of water and methanol over heat resulting in 0.082 grams (39.61% yield) of pure acetaminophen. Melting points of both crude and pure acetaminophen were taken, and found to be 165.9 - 170.9°C and 168.2 - 171.5°C, respectively. The literature melting point of acetaminophen is 169.5 – 171.0°C, indicating that our final product was pure.
This experiment involved three steps: synthesis of aspirin, isolation and purification, and the estimation of purity of the final product. The synthesis involved the reaction of salicylic acid and acetic anhydride in the presence of a catalyst, phosphoric acid, H3PO4. When the aspirin was prepared, it was isolated and filtered. The percentage yield of the synthesis was calculated to be 78.42%. The experimental melting point range of aspirin was determined to be 122 -132°C. Due to its wide range, and lower value than that of the theoretical melting point of 136°C, it was
The goal of this experiment was to synthesize aspirin. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and acetic anhydride. In the reaction the hydroxyl group on the benzene ring in salicylic acid reacted with acetic anhydride to form an ester functional group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in the solution as well as some sulfuric acid, aspirin, and acetic acid. Crystallization, which uses the principle of
The sodium hydroxide acts to pull the hydrogen off the oxygen in the 2-methylphenol so that the oxygen has a negative charge and can attack the sodium chloroacetate. Again, using a 1:1 molar ratio, 0.34 g (2.9 mmol) of sodium chloroacetate (the good leaving group) was added to 1 ml of water and dissolved. Following dissolving all of the 2-methylphenol (to avoid the sodium hydroxide reacting concurrently with the sodium chloroacetate and 2-methylphenol) in the sodium hydroxide, the aqueous solution of sodium chloroacetate was transferred to the reaction flask. This mixture was then heated to reflux, using a medicine dropper affixed to the top of the flask as an alternative method to boil without
9-anthraldehyde and (carbethoxymethylene)triphenylphosphorane were reacted together using the Wittig reaction to produce E-3-(9-Anthryl)-2-propenoic acid ethyl ester. .100 g of 9-anthraldehyde and .180 g of (carbethoxymethylene)triphenylphosphorane were used. 9-anthraldehyde was a green powder while (carbethoxymethylene)triphenylphosphorane was a white powder. Both were added together into a 3.00 mL conical vial with a magnetic spin valve. The vial was inserted into a 120 C sand bath to melt the reagents. Once the reagents melted, they were stirred for 15 minutes (2:30 pm-2:45 pm). After stirring, the vial was removed to cool to room temperature. 3.00 mL of hexanes were added to the vial and the suspension was stirred. The solvent was removed
The purpose of this lab is to investigate the composition of a compound suspected to be Panacetin, a type of pain-killer. Panacetin is typically made up of sucrose, aspirin, and acetaminophen, but the third component in this experiment is unknown. The unknown component is suspected to be a chemical relative of acetaminophen, either acetanilide or phenacetin. Using techniques such as extraction, evaporation, and filtration, the three components will be isolated based on their solubilities and acid-base properties. Then, the percent composition of Panacetin can be deduced based on the masses of the three dried components. The
Pre-Lab: Analgesic drugs are known for reducing pain, while antiseptic drugs reduce symptoms such as fevers and swelling. However, some of these drugs can reduce both illnesses. To obtain a pure compound in these drugs, the scientist needs to separate the desired compound by taking advantage of the different physical and chemical properties. Such as; different boiling points, melting points and their solubility properties. To do this a chemist can also asses the differences between acidic and basic substances when they are added to water soluble mixtures. Within this current experiment I will asses the
The purpose of this lab was to synthesize aspirin, determine the theoretical yield, compare the percent yield to the theoretical yield and test the purity of aspirin by adding Iron (III) chloride to the product.
This experiment was designed by conducting a substitution reaction to construct a complex compound (2-methylphenoxyacetic acid) from two simple parts; also known as synthesis - converting simple molecules into more complex molecules. A purification technique known as crystallization was used to purify the product. Suction filtration was used to filter out the product. The experiment was completed over a three-day experimental period.
Table 1: Properties of the reagents and possible products for the reaction. The boiling point of Phosphoric acid is not important because it is a reagent.
In this experiment, thin layer chromatography (TLC) was used to identify and compare polarity of two molecules, caffeine and acetaminophen. Chromatography is defined as the separation of a mixture of chemicals as they flow at different rates over a stationary phase based on their relative polarity. Caffeine, the more polar molecule had a greater affinity for the polar silica gel stationary phase causing it to consistently have a lower retention factor regardless of the mobile phase. This methodology can be effectively used to distinguish and analyze the polarity various of chemical mixtures such as within medicines, inks, etc.
The majority of acetaminophen, approximately 90%, will be metabolized by glucuronidation (Lancaster et al., 2015). Approximately 10% will be metabolized by cytochrome p450 (Lancaster et al., 2015). From there it will become the reactive metabolite N-acetyl-p-benzo-quinone imine (NAPQI) (Lancaster et al., 2015). Under normal circumstances, glutathione (GSH) will convert NAPQI to a nontoxic metabolite (Lancaster et al., 2015). In cases where GSH depletion is present due to acetaminophen overdose, malnutrition, or alcoholism, NAPQI cannot be converted, leading to increased NAPQI levels and subsequently liver damage (Lancaster et al.,
An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the