Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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provide all reagents and structure but not required more than four steps.

Transcribed Image Text:### Electrophilic Aromatic Substitution: The Acetylation of Salicylic Acid
**Objective:**
Investigate the electrophilic aromatic substitution reaction involving the acetylation of salicylic acid to yield an essential pharmaceutical compound. This activity demonstrates key principles of organic chemistry, particularly electrophilic aromatic substitution and functional group transformations.
**Background:**
Electrophilic aromatic substitution is a fundamental reaction in organic chemistry, where an electrophile replaces a hydrogen atom on an aromatic ring. Salicylic acid is often used in such reactions due to its medicinal properties and reactivity.
**General Strategy:**
To convert salicylic acid into a desirable final product, an acetylation reaction is performed. Acetylation adds an acetyl group (CH₃CO) to the molecule, enhancing its pharmacological effectiveness. The process involves:
1. **Formation of the Electrophile:**
- The electrophile in this case is the acetyl cation, generated from acetic anhydride (or acetyl chloride) in the presence of a catalyst like sulfuric acid.
2. **Mechanism:**
- The aromatic ring of salicylic acid acts as a nucleophile, attacking the acetyl cation, leading to the formation of an acetylated intermediate.
- The intermediate quickly rearomatizes, expelling the leaving group and restoring the aromaticity of the system.
3. **Final Product:**
- Through this process, salicylic acid transforms into acetylsalicylic acid, commonly known as aspirin, a widely used analgesic.
**Diagram Explanation:**
- **Starting Material:**
- The aromatic ring bonded to a carboxylic acid group (COOH) and a hydroxyl group (OH).
- **Final Product:**
- The aromatic ring now contains an ester functional group, resulting in a lactone ring structure with a dimethyl substituent (CH₃ groups).
This transformation underscores the practical applications of organic reactions in synthesizing vital medicinal compounds and demonstrates reaction mechanisms in real-world chemistry.
Expert Solution
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Organic reaction mechanisms:
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