UNIVERSITI SAINS MALAYSIA

SCHOOL OF CHEMICAL ENGINEERING

EKC 107/3 – ORGANIC CHEMISTRY

LABORATORY COURSE

Name of student : Chin Jin Wei

Matrix Num : 108223

Name of partner : Nor Hasni Binti Abdul Saat

Matrix Num : 108250

Group : B2

Instructor : Prof. Madya Dr. Mashitah Mat Don

EXPERIMENT: SYNTHESIS OF ASPIRIN

Experiment 2: Purification Test

Test Tube Observation/Explanation

Water + salicylic acid + ferric chloride Dark purple colouration formed. Ferric chloride
reacts with the phenol group on the salicylic
acid to form a purple complex.

Water + product of experiment + ferric The solution turn light purple. There is no
chloride phenol group presents in the product of the
experiment. The aspirin synthesized does not
contain a phenol group. However, since aspirin
is added to 0.5ml of water, it will undergo
hydrolysis, forming salicylic acid and acetic
acid (vinegar).therefore, light purple complex
formed since salicylic acid from the hydrolysis
of aspirin is of lower concentration.
Water + ferric chloride The solution remains colourless due to the
absence of salicylic acid. This is act as a control
sample.

QUESTION:

1. The important material for preparation of aspirin is salicylic. Preparation

process of salicylic acid using phenol is known as Kolbe-Schmitt Reaction.
Discuss this reaction process in details.

The Kolbe-Schmitt Reaction is a carboxylation chemical reaction that proceeds

by heating sodium phenolate with carbon dioxide under pressure 100 atm at
125°C. The product is then treated with sulfuric acid. The final product obtained
is an aromatic hydroxy acid which is also known as salicylic acid, the precursor
to aspirin.
 Mechanism:

This reaction undergoes the aromatic electrophilic substitution reaction between

carbon dioxide and sodium phenoxide. Then it will form three transition states
and three intermediates. In the first step of the reaction, a polarized O-Na bond
of sodium phenoxide is attacked by the carbon dioxide molecule and the
intermediate NaPh-CO2 is formed. Then, the electrophilic carbon atom attacks
the ring primarily at the ortho position, it forms two new intermediates. Sodium
salicylate is then formed by a 1, 3-proton shift from C to O atom. Salicylic acid
can then be obtained through acidification.

2. Salicylic acid is one of the phenol groups while acetylsalicylic acid is not a
phenol group. Explain this statement.

Salicylic acid is one of the phenol groups

because it contains a benzene ring which has hydroxyl group (-OH). The presence of the
phenol group can be tested by using ferric chloride. When salicylic acid react with ferric
chloride, purple colouration will be formed, then it has been proven that salicylic acid is
one of the phenol groups.
Aspirin is not a phenol because it does not contain any hydroxyl group that is attached
directly to the benzene ring. It is a kind of ester. Hence, aspirin react with ferric chloride,
there is no purple solution form. Then we can say that aspirin is not a phenol. This is
because aspirin will not reacted with ferric chloride. However, once aspirin has been
hydrolysed, salicylic acid and acetic acid (vinegar) will be formed. Thus, reaction with ferric
chloride will form light purple complex.

References:
• http://en.wikipedia.org/wiki/Kolbe–Schmitt_reaction
• Hermann Kolbe (1860). "Ueber Synthese der Salicylsäure". Annalen der Chemie und
Pharmacie 113 (1): 125–127
• http://www.organic-chemistry.org/namedreactions/kolbe-schmitt-reaction.shtm

• http://www.chymist.com/DRUG%20TESTING.pdf