CHEM 1015

GENERAL CHEMISTRY 1 (LAB)

FALL 2022

Experiment 1
Preparation of Aspirin
 Objectives of the experiment

• Preparing aspirin.
• Using recrystallization to purify the
product.
• Using the melting point and ferric
chloride test to check the purity of the
product.
 Acetyl salicylic acid (Aspirin)
Reduces fever, pain, swelling, soreness, and redness, as
well its anti-clotting properties

Leaves of Willow tree

Hydrolysis of Aspirin at T>60 °C
 Procedure
• Preparation of Crude Aspirin
1

• Filtration and Drying

2

• Purification by Recrystallization
3

• Purity Testing (Ferric chloride

4 and Melting point tests)
• The acetic anhydride is destroyed by water. All glassware
must be dry.
• The reaction of acetic anhydride with water can be violent.
• Acetic anhydride and conc. sulfuric acid should be
handled inside the fumehood.
• The amounts of material are small. It would be easy to
loose ALL of your aspirin.
 1
• Preparation of Crude Aspirin

Conical flask (1) Glass rod (1) Test tubes (3)

Wash and Dry (see General Practice Section)

1. Introduce the following reagents in the given order

into the clean dry conical flask:
• 1 gram of salicylic acid (use the balance and weighing
paper)
• 2 mL of acetic anhydride (use 10 mLmeasuring cylinders)
• 0.5 mL (5 drops) of conc. sulfuric acid
 1
• Preparation of Crude Aspirin

2. Vigorously stir the reaction mixture

with the dry glass rod until a heavy
white precipitate. This is crude
aspirin. (you can feel some
exothermicity during the reaction)
3. Place the conical flask in an ice bath
to cool down.
4. Add 25 mL of distilled water to the
crude aspirin to dissolve acetic acid,
sulfuric acid and unreacted acetic
anhydride.
 • Filtration and Drying
2
• Put a filter paper (that covers the holes) in the funnel
and wet it with distilled water.
• Tightly fit the funnel in the rubber ring, and place it
over the mouth of the filter flask.
• Connect the flask to the vacuum line and open the tap
to create a suction force and strongly press the funnel
onto the rubber ring to eliminate any air leakage
• Pour the suspension into the funnel for filtration.
• Rinse the conical flask with some distilled water and Vacuum filtration using
pour this into the funnel. the Buchner funnel
(why?)
• When filtration is complete, close off the vacuum line and transfer the filtered
crude aspirin onto a filter paper and press with another filter paper to dry.
• Save a small amount of the crude aspirin in a dry test tube for ferric chloride test
(Label as crude Aspirin)
 • Purification by Recrystallization
3
This purification process purifies the crude aspirin from
unreacted chemicals and byproducts.
Crystallization Procedure
1. Warm 5 mL of ethanol and 15 mL of distilled water in two separate beakers to 50 °C
on an electric hot plate.
2. Add the crude aspirin to the warm ethanol (why?), stir, and then pour the mixture over
the warm distilled water (why?). Stir well to dissolve the aspirin. Warm ethanol
dissolves aspirin. Warm water dissolves impurities.
3. Watch out that the temperature never exceeds 60 °C, otherwise hydrolysis of aspirin
will occur.
4. Cool the mixture in an ice bath without stirring (why?). Within about 10 minutes,
needle-like crystals appear. (Cooling will help aspirin crystallization as its solubility
decreases with cooling)
5. Filter these crystals using vacuum filtration and then dry on a filter paper.
6. Save a small amount of the purified aspirin in a dry test tube for ferric chloride test
(Label Purified Aspirin).
 • Purification by Recrystallization
3

Wrap the remaining sample of purified

aspirin in filter paper, label it with
your name and hand it over to the
instructor who will leave it to dry in a
drawer till the following lab session.
This will then be used for melting
point determination.
 • Purity Testing (Ferric chloride tests)
4
Phenol
• In addition to the two labeled test tubes with samples of your
crude aspirin and purified aspirin, in a third clean, dry and
labeled test tube, introduce a few crystals of salicylic acid
(why?). Ferric chloride
• Add about 1 mL of ethanol into each test tube and shake to
dissolve the samples.
• Add 1 to 2 drops of ferric chloride to each test tube.
• Record your observations.
• Ferric chloride test is positive (color change) with compounds
containing a phenolic group.
 • Purity Testing (Ferric chloride tests)
4
• The test with crude aspirin is a rough
indication of the completion of the
synthesis reaction.
• For the purified aspirin, the test is an
indication of the purity of the product,
also indicating if any hydrolysis has
taken place during recrystallization.
 • Purity Testing (melting point tests)
4
• Make sure the thermometer in the equipment
for melting point determination does not
record a temperature higher than 60 °C before
putting your sample, otherwise wait until the
machine cools down.
• Spread a very small amount of your purified
aspirin between two glass slides, place in the
equipment, then turn it on.
• Record the temperature (T1) when the sample starts to melt.
• Record the temperature (T2) when the sample has melted completely.
• Calculate the average melting point from T1 and T2 ((T1+T2)/2).
• The difference between the melting point of the purified aspirin and the
theoretical value reflects the purity of the prepared aspirin.