Exam (elaborations)

Organic Chemistry in The Real World (The History and Making of Aspirin).pdf

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Course
Chemistry

Institution
12th Grade

"Organic Chemistry in The Real World: The History and Making of Aspirin" is an engaging assignment that delves into the fascinating world of organic chemistry through the lens of a widely recognized medication. In this comprehensive document, students explore the historical evolution of aspirin, tr...

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Uploaded on May 17, 2024
Number of pages 9
Written in 2023/2024
Type Exam (elaborations)
Contains Questions & answers

Institution Secondary school
Education 12th Grade
Course Chemistry
School year 1

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Babatunde 1

First and last name
Teachers name
Class
Date
The History and Making of Aspirin
1) What was willow bark used for ? What was the active ingredient in Willow Bark found to
be? Give its structure and identify any functional groups.

Willow bark has been historically used for
medicinal purposes, and the active ingredient
found in it is salicylic acid. The chemical
structure of salicylic acid includes a benzene
ring with a phenol (HO) group and a carboxylic
acid (COOH) group (Figure 1). It can also be
written as C7H6O3 as its condensed form
(Toppr). Salicylic acid is known for its
anti-inflammatory and pain-relieving properties,
and it is the natural substance related to
synthetic aspirin. Interestingly, the use of willow
leaves containing salicylic acid dates back to
ancient times, with mentions in Assyrian clay
tablets around 4000 years ago and recommendations by Hippocrates for fever and pain
(International Aspirin Foundation). The first scientific study of willow bark benefits was
conducted by Reverend Edward Stone in 1763, and the synthesis of acetylsalicylic acid
(ASA), the stable form of aspirin, was achieved in 1897 by Dr. Felix Hoffman, marking
the birth of both aspirin and the pharmaceutical industry (Montinari, 2018). Aspirin has
since played a significant role in preventing cardiovascular diseases and is also being
explored for its potential in cancer prevention and management.

2) Modern Aspirin has the name acetylsalicylic acid. Give its structure.

The structure of aspirin, or acetylsalicylic acid, is depicted as a planar molecule. The
central feature of its structure is a benzene ring which forms the core of the molecule.
Two functional groups are attached to this ring in the ortho position, the functional

, Babatunde 2

groups are placed on the first and second carbon of the benzene ring (Helmenstine,
2019): the first is a carboxylic acid group (COOH), and the
second is an ester group (COOCH3), derived from acetic acid
(Figure 2). This arrangement gives aspirin its distinct
properties and medicinal effects.

3) Describe the chemical process that converts the active
ingredient of Willow Bark to acetylsalicylic acid. Give the full
chemical reaction and describe what is occuring in each step.

The chemical process converting the active ingredient of
Willow Bark, salicylic acid, to acetylsalicylic acid (aspirin) is an
acetylation reaction. In the presence of a catalyst, often sulfuric
acid, salicylic acid reacts with acetic anhydride. The hydroxyl
group (OH) in salicylic acid undergoes acetylation, resulting in the replacement of a
hydrogen atom with an acetyl group (COCH3) from acetic anhydride. This transforms
salicylic acid into acetylsalicylic acid, known as aspirin, and produces acetic acid as a
byproduct. Aspirin retains the therapeutic properties of salicylic acid but with improved
tolerability (Garcia, 2016). The reaction is crucial in the synthesis of aspirin, a widely
used medication with anti-inflammatory, analgesic, and antipyretic effects.

1. Salicylic acid serves as the initial compound. It contains a hydroxyl group (-OH) in its
structure.

2. Acetic anhydride is the acetyl group donor in the acetylation process. It provides the
acetyl group for the reaction.

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