Reaction Mechanism in the

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.