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SYNTHESIS OF

ASPIRIN

Lopez, Patricia | 2PSY1

Aspirin or Acetylsalicylic Acid

Synthesis Reaction

* Functional Groups present:


1. Ester
2. Carboxylic Acid

ESTERIFICATION
The process of making Aspirin.
Reaction between a carboxylic acid and an alcohol to form an ester.
* In this experiment, a strong acid catalyst (Sulfuric acid) was used to
speed up the reaction.
* Acetic Anhydride is much more reactive in contrast to acetic acid.

Salicylic Acid Aspirin Mechanism

Limiting Reagent & Percent Yield


1. Determine the molar ratio of the reactants actually used relative to the
stoichiometric molar ratio as defined in the balanced equation of the reaction

1.04!!

Salicylic Acid:

! = 0.007541!!"#!
138.121
!"#

Acetic Anhydride:

1.08!!
2!!"!
! = 0.0212!!"#
102.09
!"#

Limiting Reagent

Excess Reagent

Aspirin (Theoretical Yield):


2. The % yield of the experiment is
then determined from the ratio of the
amount of product actually obtained
to this theoretical amount (mass or
moles can be used for the
calculation.)

1.04!!!

1
! ! 1 !!180.157 = 1.35!
138.121
!"#
Percent Yield:

0.741!!!
!100 = !". !"
1.35

Laboratory Techniques
1.Vacuum filtration
- commonly used procedure to separate a solid
from a liquid.
- consists of a Buckner funnel, paper filter,
single-hole rubber stopper, ring stand and clamp,
filter flask and vacuum tubing connecting the flask
to an aspirator.

2. Recrystallization
- changes in the solubility of a compound as
temperature changes

Assume

Recrystallization
Solvents used in the recrystallization process must be
matched to the compound being purified. The attributes of
a suitable solvent include:
> The solute particles are generally insoluble in cold
solvent, but soluble in hot solvent.
> The solvent should have a steep solubility vs
temperature curve for the solute.
> The boiling point of the solvent must be less than the
melting point of the solute.
> The solvent should not react with the solute.

Recrystallization
The solubility of an organic compound is a
function of the polarities of both the solvent and
the solute. Thus, the term Like Dissolves Like
indicates that:
- Polar solvents dissolve polar solutes.
- Nonpolar solvents dissolve nonpolar solutes.

FeCl3 Test