Exp 1 Synthesis of Aspirin

There are many different ways that the field of chemistry can be divided into sub-fields. One way to
do this is by grouping what is studied, or how it is studied. For example chemistry is often divided into the
topics of Organic chemistry, Analytical chemistry, Inorganic Chemistry, Biological Chemistry, and
Physical chemistry. Organic Chemistry is the study of molecules that contain carbon: how they are made
and what their properties are. Analytical chemistry is the study of how much of a chemical is present.
Inorganic chemistry is the study of molecules containing elements other than just carbon, nitrogen, oxygen
and hydrogen. Physical Chemistry involves the measurement of physical properties of chemical
compounds. There are of course other ways that the broad field of chemistry can be divided. For instance
some chemists are primarily interested in making new molecules. These chemists might be inorganic
chemists or organic chemists, but they can also be considered synthetic chemists. In this lab you are going
to perform an organic synthesis by making aspirin.

Organic chemistry covers a large class of molecules, all of which contain carbon and hydrogen.
Other elements can also be found in molecules that are considered to be organic, such as nitrogen, oxygen,
sulfur, and phosphorous. When the molecules contain only carbon and hydrogen they are called
hydrocarbons. There are a large number of molecules that are hydrocarbons- from something as simple
as methane ( CH4) to the polymer polyethylene ( [CH2]x) where x can be hundreds or even thousands.
Because organic chemistry deals with so many compounds, a way to organize them based on their
similarities is used. The hydrocarbons would be one such classification. Others are based on the types of
atoms present in the molecule and how they are arranged- called the functional groups of the molecules.
Aspirin contains oxygen atoms as well as carbon and hydrogen. The oxygen atoms are present in two
different types of functional groups. One of these functional groups is a carboxylic acid, while the other is
called an ester. Figure 1 contains a general diagram of both of these groups, as well as a diagram of the
structure of aspirin. The letter R in the figure is generally understood to be an unspecified hydrocarbon.

Figure 1

Carboxylic acid
O-H
O
R

O
O-H
O
Ester
O CH3
O-R2

R1 C
Aspirin
O
Experiment #1

To Synthesize aspirin in this experiment we will be creating the ester functional group. Esters can
be prepared by the reaction of a carboxylic acid with an alcohol ( R-O-H). To accomplish this we will start
with the chemical salicylic acid.

Salicylic acid occurs naturally in the bark of willow trees. Prior to the 1800’s, willow bark was
often brewed into a tea, or chewed to relieve pain. While the salicylic acid is effective at reducing pain it was
found to irritate the lining of the stomach. In 1899 a German chemical company began converting salicylic
acid into the ester acetylsalicylic acid. This is the chemical known commonly as aspirin. Esterifying the
salicylic acid to give aspirin reduces the irritation of the stomach lining. The German chemical company is
still in existence today and still produces Bayer Aspirin.

Figure 2 shows the reaction of salicylic acid with acetic acid to form aspirin ( acetylsalicylic acid)
and water. Notice that the reaction is written with a double arrow to indicate that an equilibrium is formed
between the two reactants and the two products. An equilibrium is formed when the products can also react
with each other to reform the reactants. This effects the yield of the desired product.

Figure 2

O O
O
O-H H+ O-H
+ O + H2O
O-H CH3 O-H O CH3

To avid forming an equilibrium mixture we will not use acetic acid in this experiment. Instead we
will use acetic anhydride. this reaction is shown in Figure 3. This reaction produces acetic acid as a second
product instead of water. Because no water is formed in the reaction the aspirin can’t hydrolyze ( react with
water) to reform salicylic acid.

Figure 3

O O
O
O-H O O O-H
O +
+ CH3
CH3 O-H
O-H O CH3 O CH3

Page 2 Synthesis of Aspirin

Caution: Acetic anhydride can cause severe chemical burns. In case of contact with the
skin have your lab partner inform the instructor and immediately begin rinsing with
water for 15 minutes.

1. Weigh out about 2 grams of salicylic acid and record the exact weight to the nearest
0.001 g in your notebook. Place the salicylic acid in a 125 mL erlenmeyer flask.

2. Weigh out approximately 0.4g of sodium acetate into a plastic weigh boat. Again
record the exact weight (to 0.001g) in your notebook. Do Not add this to the flask
until step 4.

3. Take the flask to the fume hood along with a 10 mL graduated cylinder. Measure
out 2-3 mL of acetic anhydride. Record the exact amount you use in you lab
notebook, then add the acetic anhydride to the erlenmeyer flask containing the
salicylic acid.

4. Add the sodium acetate to the erlenmeyer flask.

5. Carefully swirl the flask to mix the reactants and place the flask in the preheated
water bath in the hood.

6. Heat the mixture for 15-25 minutes. Record the time that you begin heating the
mixture and the time that you remove the mixture from the water bath in your
notebook.

7. Using a clean graduated cylinder measure 2.0 mL of deionized water.

8. While still using the fume hood, remove the flask from the water bath and add the 2
mL of deionized water and swirl the flask. The water will react with excess acetic
anhydride to form acetic acid. The hot acetic acid vapors can be very irritating so
leave the flask in the hood for 5 minutes before returning it to our lab bench.

9. At your bench have an ice bath prepared. Add 30 mL of deionized water to the flask
and swirl. Cool the flask in your ice bath- crystal of aspirin should form. Allow the
solution to cool for 25-30 minutes. Also cool 15-20 mL of additional deionized
water in a separate beaker.

10. Set up a filter flask with a buchner funnel. Remove the erlenmeyer from the ice bath
and filter the crystals using the vacuum filter. Wash the crystals 3 times with small
portions of ice cold deionized water.

11. Allow the crystals to sit on the filter for a few minutes to remove as much water as
possible.

12. Weigh your product and record the weight to the nearest 0.001g in your lab
notebook.

13. When you have recorded your weight of aspirin, see your lab instructor for
additional directions

Synthesis of Aspirin Page 3

Page 4 Synthesis of Aspirin

1. Give the complete chemical formula for each of the following compounds

a. Salicylic acid

b. acetic anhydride

c. acetylsalicylic acid (aspirin)

2. Calculate the molar mass of aspirin. [show your work!]

3. If 0.150 moles of salicylic acid and excess acetic anhydride are used during a synthesis of aspirin, how
many grams of aspirin will be obtained if the reaction gives a 38% yield? [show your work]

Synthesis of Aspirin Page 5