CH3 CH2-CH2-CH3 KMNO4. н', heat CH3 -CH2-CH3 CH CH2-CH3 (а) (b) CH3 COOH HOOC, .COOH CH .COOH (с) (d) (е) o=3

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Chapter22: Organic And Biological Molecules
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Problem 50E: There are three isomers of dichlorobenzene, one of which has now replaced naphthalene as the main...
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What is the major product of the following reaction?
### 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
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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