SCH 4U Name:

Ms. van Gaal Date:

PREPARATION OF ASPIRIN
Introduction
Aspirin, acetylsalicylic acid, was first synthesized in 1893 by Felix Hofmann, a
chemist for the German firm of Bayer. This compound had the medicinal properties of
salicylic acid, an extract of willow bark, without the unpleasant taste or the high degree
of irritation of the mucous membranes lining the mouth, gullet, and stomach.
Aspirin is both an organic ester and an organic acid. It is used extensively in
medicine as a pain killer (analgesic) and as a fever-reducing drug (antipyretic). When
ingested, acetylsalicylic acid remains intact in the acidic stomach, but in the basic
medium of the upper intestinal tract, it hydrolyzes forming the salicylate and acetate ions.
However, its additional physiological effects and biochemical reactions are still not
thoroughly understood.  

Figure 1: The balanced structural equation for the formation of acetylsalicylic acid

Aspirin (molar mass of 180.2 g/mol) is prepared by reacting salicylic acid (molar
mass of 138.1 g/mol) with acetic anhydride (molar mass of 102.1 g/mol). Aspirin is a
weak monoprotic acid.

Object:
To synthesize the common pain relievers: aspirin

Materials Needed

Salicylic acid Beakers, 2 600-mL, 25 or Clamp

Acetic anhydride 80-mL Ice
Sulfuric acid, concentrated Graduated cylinders, 10- Ice water
Pipettes mL 1% Ferric Chloride
Erlenmeyer flask, 250-mL Stirring rod 2 test tubes
Ring stand

Procedure

1. Prepare a hot water bath in a 600ml beaker using 300 ml of water.

2. Weigh out 4.0 g of salicylic acid. Place it in a 250-mL Erlenmeyer flask.

SCH 4U Name:
Ms. van Gaal Date:
3. In a fume hood, add 8 mL of acetic anhydride. Swirl the flask to wet the salicylic acid
crystals.

4. In a fume hood, add 4 drops of concentrated sulfuric acid, H2SO4, to the mixture.

5. At your lab bench, gently heat the flask in a boiling water bath for about 10-15
minutes.

6. Remove the flask from the hot water bath and add 20 mL of deionized ice water to
decompose any excess acetic anhydride.

7. Make an ice bath by placing some ice and 200ml of cold water in a 600ml beaker.
Chill the solution in an ice bath until crystals of aspirin no longer form, stirring
occasionally to decompose residual acetic anhydride. If an "oil" appears instead of a
solid, reheat the flask in the hot water bath until the oil disappears and again cool.

8. Determine the mass of a piece of filter paper to the nearest 0.1 g and setup a
filtration apparatus. Carefully filter the contents of the flask and wash out the flask
using l-2ml of ice water at a time. Do not exceed 20 ml of water. Be sure to gently mix
around your crystal to help remove excess water.

9. At the end of the period gently remove your filter paper and product and allow it to
dry on a clean watch glass over night.

10. Determine the mass of the dry filter paper and crystals.

FERRIC CHLORIDE TEST FOR SALICYLIC ACID

1. Take 5ml of distilled water and add 5mL of ferric chloride.

2. Dissolve a small amount the product you made in 2 ml of distilled water. Add 5 mL
of aqueous 1% ferric chloride solution to the test tube and note the colour.
3. Now perform this same test with salicylic acid.
4. Formation of an iron-phenol complex with Fe(III) gives a definite color ranging from
red to violet, depending upon the particular phenol present. A strong purple colour
suggests the strong presence of the salicylic acid.
4. Record your observations.

Results: Report your percentage yield. Create your own table for observations and data.

Discussion: Use secondary sources to discuss and support the success of you lab and
interrupt any test results. Sources of error should be discussed as well as possible
amendments to your lab.

Calculations: Show all calculations in this section.

SCH 4U Name:
Ms. van Gaal Date:

Lab Report Rubric

Beginning Developing Accomplished Exemplary
1 2 3 4
Introduction Very little Some introductory Introduction is nearly Introduction complete
background information, but still complete, missing and well-written;
information provided missing some major some minor points provides all necessary
or information is points background principles
incorrect for the experiment
Hypothesis/ The purpose of the The purpose of the lab The purpose of the The purpose of the lab
Purpose lab or the question to or the question to be lab or the question to or the question to be
be answered during answered during the lab be answered during answered during the
the lab is erroneous is partially identified, the lab is identified, lab is clearly identified
or irrelevant and is stated in a but is stated in a and stated.
somewhat unclear somewhat unclear
manner. manner.
Results: Figures, graphs, Most figures, graphs, All figures, graphs, All figures, graphs,
data, figures, tables contain errors tables OK, some still tables are correctly tables are correctly
graphs, tables, or are poorly missing some important drawn, but some have drawn, are numbered
etc. constructed. or required features minor problems or and contain
could still be titles/captions.
improved
Discussion The discussion does Some explanation of Good explanation of Excellent explanation
not explain any of the results using student’s results using of results using
results with sufficient own thoughts and student’s own student’s own thoughts
detail. background sources. thoughts and and background
background sources. sources.
Discussion: There is no Experimental errors and Experimental errors Experimental errors,
Error discussion of errors revisions to procedure and their possible their possible effects,
Analysis/ or other possible are mentioned. effects are discussed. and ways to reduce
future scientific tests. Future experimental errors are discussed.
experiments adjustments are Future experimental
discussed. adjustments are
discussed and
supported with
background sources.
Scientific Report illustrates Report illustrates a Report illustrates an Report illustrates an
Concepts inaccurate limited understanding accurate accurate and thorough
-questions understanding of of scientific concepts understanding of understanding of
answered scientific concepts underlying the lab. most scientific scientific concepts
-calculations underlying the lab. concepts underlying underlying the lab.
the lab.
Components Several required One required element is All required elements All required elements
of the Report elements are missing. missing, but additional are present. are present and
elements that add to the additional elements
report (e.g., thoughtful that add to the report
comments, graphics) (e.g., thoughtful
have been added. comments, graphics)
have been added.
Background Material is directly A few background A few reputable Several reputable
Sources copied rather than put sources are used and background sources background sources
into student's own cited correctly, but are used and cited were used and cited
words and/or some are not reputable correctly. Material is correctly. Material is
background sources sources. Material is translated into translated into student's
are cited incorrectly. translated into student's student's own words. own words.
own words.
Very frequent
Grammar & Only one or two All grammar and
grammar and/or More than two errors.
Spelling errors. spelling are correct.
spelling errors.
Comments: Overall Level: _____