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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What is the major product of the following reaction?
Transcribed Image Text:### Benzene Side Chain Oxidation with Potassium Permanganate (KMnO₄)
#### Description
The diagram illustrates the oxidation reaction of an alkyne-substituted benzene compound using potassium permanganate (KMnO₄) under acidic conditions with heat. The starting material and several potential products are presented as follows:
1. **Starting Material:**
- **Structure:** Methyl-(n-propyl)benzene (C₆H₅C₃H₇CH₃)
2. **Reagent:**
- **Potassium Permanganate (KMnO₄)** in acidic (H⁺) conditions and heat.
3. **Potential Products:**
- **(a)** An aliphatic ketone-substituted benzene compound (C₆H₅C(=O)(CH₂)₂CH₃)
- **(b)** An aliphatic ketone-substituted benzene compound (C₆H₅C(=O)CH₂CH₃)
- **(c)** 4-Methylbenzoic acid (C₆H₄(CH₃)COOH)
- **(d)** Benzenetricarboxylic acid (C₆H₃(COOH)₂)
- **(e)** Terephthalic acid (C₆H₄(COOH)₂)
#### Explanation of Reaction
Benzene side chain oxidation with potassium permanganate primarily results in carboxylic acids, especially when the side chain is a primary or secondary alkyl group. The general outcome of this reaction is the conversion of side chains into carboxylic acid groups (-COOH).
The most probable product from the given reagents and conditions is compound **(e)**, terephthalic acid. This is because KMnO₄ is a strong oxidizing agent that cleaves C-C bonds adjacent to the benzene ring, converting alkyl groups completely into -COOH groups.
#### Diagram Explanation
The diagram starts with a benzene ring substituted with a propyl group (CH₂-CH₂-CH₃) and a methyl group (CH₃), being subjected to oxidation by KMnO₄. The resulting possible compounds demonstrate various stages of oxidation:
- Compounds **(a)** and **(b
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