Aspirin (acetylsalicylic acid) is a well-known pain reliever and anti-inflammatory drug. However, it can cause stomach irritation in some individuals. Acetaminophen, another common pain reliever, is gentler on the stomach but lacks the anti-inflammatory properties of aspirin. Here's a challenge that combines organic chemistry concepts!The Task: Develop a two-step synthesis plan to convert aspirin (acetylsalicylic acid) into acetaminophen (N-acetyl-p-aminophenol).Clues and Considerations:Aspirin has an ester functional group (carbonyl bonded to an oxygen and then an alkyl group).Acetaminophen has an amide functional group (carbonyl bonded to a nitrogen and then a carbon).Both molecules share a similar aromatic ring structure with a hydroxyl group (-OH) attached.Possible Steps:Step 1: What kind of reaction could be used to break the ester bond in aspirin?Step 2: How can the resulting intermediate be transformed into an amide group to yield acetaminophen?Bonus Challenge:Identify the reagents required for each step of your proposed synthesis.
Question
Aspirin (acetylsalicylic acid) is a well-known pain reliever and anti-inflammatory drug. However, it can cause stomach irritation in some individuals. Acetaminophen, another common pain reliever, is gentler on the stomach but lacks the anti-inflammatory properties of aspirin. Here's a challenge that combines organic chemistry concepts!The Task: Develop a two-step synthesis plan to convert aspirin (acetylsalicylic acid) into acetaminophen (N-acetyl-p-aminophenol).Clues and Considerations:Aspirin has an ester functional group (carbonyl bonded to an oxygen and then an alkyl group).Acetaminophen has an amide functional group (carbonyl bonded to a nitrogen and then a carbon).Both molecules share a similar aromatic ring structure with a hydroxyl group (-OH) attached.Possible Steps:Step 1: What kind of reaction could be used to break the ester bond in aspirin?Step 2: How can the resulting intermediate be transformed into an amide group to yield acetaminophen?Bonus Challenge:Identify the reagents required for each step of your proposed synthesis.
Solution
The synthesis of acetaminophen from aspirin can be achieved in two steps:
Step 1: Hydrolysis of Aspirin (Acetylsalicylic Acid) The ester bond in aspirin can be broken down by a process called hydrolysis. This reaction involves the addition of water (H2O) to the ester bond, which breaks it apart. The reaction is catalyzed by an acid or a base. In this case, we can use a strong base like Sodium Hydroxide (NaOH) to catalyze the reaction. The products of this reaction are salicylic acid and acetic acid.
Step 2: Acetylation of p-Aminophenol The salicylic acid obtained from the previous step can be converted into p-aminophenol through a series of reactions involving nitration, reduction, and hydrolysis. The p-aminophenol can then be acetylated to form acetaminophen. This reaction is typically carried out using acetic anhydride (CH3CO)2O as the acetylating agent. The product of this reaction is acetaminophen and acetic acid.
Bonus Challenge: The reagents required for each step of the proposed synthesis are:
Step 1: Sodium Hydroxide (NaOH) and Water (H2O) Step 2: Nitric Acid (HNO3) and Sulfuric Acid (H2SO4) for nitration, Tin (Sn) and Hydrochloric Acid (HCl) for reduction, Water (H2O) and Sodium Hydroxide (NaOH) for hydrolysis, and Acetic Anhydride ((CH3CO)2O) for acetylation.
Similar Questions
Aspirin (acetylsalicylic acid) was synthesised in the following experiment:8.25 g of salicylic acid (Msalicylic acid = 138.13 g mol–1) was reacted with 10.0 g of ethanoic anhydride (Manhydride = 102.10 g mol–1) in the presence of a concentrated sulfuric acid catalyst. 8.55 g of a white solid was collected at the end of the reaction.salicylic acid + ethanoic anhydride → acetylsalicylic acid + ethanoic acidCalculate the percentage yield of aspirin. State your answer to three significant figures. Maspirin = 180.17 g mol–1.
Aspirin is known as :acetyl salicylic acidphenyl salicylateacetyl salicylatemethyl salicylic acid
Although acetylsalicylic acid (aspirin) is a well-known and widely used analgesic and anti-inflammatory agent, copper(II) acetylsalicylate, a copper complex formed from aspirin and copper, has also been found to exhibit some distinctive and potentially beneficial pharmacological properties. Formation of copper(II) acetylsalicylate is achieved by dissolving an aspirin salt in water (Reaction 1) and then introducing Cu2+ ions which bind to the conjugate base of aspirin, acetylsalicylate (C9H7O4−), as outlined in Reaction 2.NaC9H7O4(s) ⇄ Na+(aq) + C9H7O4−(aq)Reaction 14 NaC9H7O4(aq) + 2 CuSO4(aq) → Cu2(C9H7O4)4(s) + 2 Na2SO4(aq)Reaction 2Using Reaction 2, a researcher synthesized a sample of copper(II) acetylsalicylate for analysis. A small volume of 0.50 M aqueous copper(II) sulfate (molar mass = 159.6) was mixed into 100 mL of filtered, saturated aqueous sodium acetylsalicylate (molar mass = 202.2) at room temperature and slowly stirred. Formation of copper(II) acetylsalicylate (molar mass = 843.7) was immediately observed as a bright blue precipitate. The precipitate was then isolated by filtration and dried, affording the product complex in high yield.Adapted from: Seguel GV, Rivas BL, Contreras JG. Synthesis and characterization of copper complexes: interaction of metalliccarboxylates with 1,3-thiazole ligand. Journal of the Chilean Chemical Society. 1970; 58(4):1967. Question 29In Reaction 2, just prior to precipitation, what is the ratio of the concentration of copper(II) acetylsalicylate to the concentration of sodium sulfate?A.1/4B.1/2C.2/2D.2/1
Select ALL the functional groups found in aspirin:Group of answer choicesketonealdehydecarboxylic acidamideesteralcoholamine
Write the reaction mechanism to prepare aspirin using concentrated sulfuric acidas a catalyst.
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