Synthesis of ASPIRIN Prepared by: Chariezza Lei J. Sanglad Erlindo Regala Melanie Ramos Objective:
1. To be able to show the reaction mechanism in the
synthesis of aspirin. Introduction Organic compounds are a certain type of compounds that contain carbon. The name “organic” is derived from the once-believed assumption that they could only be isolated from plants or made using substances taken from such organic sources. The organic molecule actually synthesized in this experiment is Acetylsalicylic Acid, commonly known as Aspirin. Acetylsalicylic Acid is derived from Salicylic acid, which then reacts with Acetyl Anhydride as per the following reaction in Figure 1.1: Figure 1.1: Reaction of Salicylic Acid and Acetic Anhydride to form Aspirin and Acetic Acid The rings shown in the Salicylic acid and Aspirin molecules are hexagonal rings of carbon compounds, with alternating single and double bonds as indicated by the double lines. There are Hydrogen atoms bonded to some of the carbon molecules as well, but these are not shown for the sake of simplicity. The mechanism of the reaction is more complicated than this, however. Many intermediary steps happen in between the first and last steps, however. These can be seen in Figure 2, which shows the mechanism of the reaction in the presence of H2SO4, a catalyst. Theory: Preparing esters from an alcohol and a carboxylic acid using an acid as catalyst is one of the most useful reactions in an organic chemists toolbox. In this experiment, aspirin was prepared from salicylic acid and acetic anhydride using sulfuric acid as a catalyst. In this reaction, the –OH on the salicylic acid acts as the alcohol and the acetic anhydride acts like a carboxylic acid. Substituting Lewis structures for molecular formulas in chemical reactions provides more information. It let's us know not just the composition of reactants and products but their structure as well. From that structure we can begin to understand why and how chemical reactions occur. Why one bond forms and another breaks. The mechanism of this reaction can be understood by examining the Lewis structures of each reagent. It is necessary to consider resonance forms of intermediate structures. These resonance forms will help us understand why a partial positive charge appears on the carbon atom in acetic anhydride and how this results in a new bond forming at that carbon. Figure 1.2. Reaction Mechanism of the Synthesis of Aspirin Mechanism
Sulfuric acid is added as a catalyst. The synthesis is
acid catalyzed. First there is a reversible reaction in which the oxygen of the carbonyl of the acetic anhydride is protonated. This increases the electrophilicity of the carbon of that carbonyl. The oxygen of the phenol in salicylic acid acts as a nucleophile and attacks the carbon of the carbonyl within acetic anhydride and simultaneously breaks the π-bond to oxygen. This forms a tetrahedral intermediate. A series of proton transfers occur. The electrons on the oxygen of the hydroxyl group on the tetrahedral intermediate, ultimately come down and reform a carbonyl group, this simultaneously induces an acetic acid to leave. After one additional proton transfer, the final aspirin is formed.