Reagents used to convert Toluene to Benzoic acid?

In summary, the question is asking for the reagents needed to transform toluene into benzoic acid. The suggested reagent is KMnO4, which is commonly used in organic chemistry for oxidization reactions. Organic chemistry often involves using proven methods and reagents rather than trying to find new ones, unless necessary for a new synthesis or improvement on existing methods.
  • #1
stratz
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Homework Statement


Identify the reagents you would use to perform the following transformation:
Toluene -> Benzoic acid

Homework Equations


N/A

The Attempt at a Solution


I'm not exactly sure how I solve this type of thing. I was considering reacting this with an ordinary oxidizing agent, but apparently KMnO4 is used specifically. But why exactly is that? It seems that our textbook wants to take these things at face-value simply by telling us that this type of reagent is used, then proceeds to give problems containing reactants that are not covered in its explanation of the chapter. So I'm wondering if you could help me with learning how to figure these out.
 
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  • #2
Can't say I remember much from orgo, but I am under impression in large parts it is about using what has been proven to work (which, sadly, to a large extent translates into memorization). Don't get me wrong, I am not saying that orgo is just about memorization. It is just that we have an almost unlimited selection of oxidizing agents, and in theory every one of them can work, but at the same time we know that for a specific reaction some are much better than the others so we don't bother with selection, we just stick to what was tested and worked OK.

Knowledge about possible oxidizing agents will become important once you have to deal with some new synthesis, one that was not tried before, or if you will on a purpose be looking for something better (cheaper, faster, more selective) than the reagent typically used as of today.
 

1. What is the purpose of converting Toluene to Benzoic acid?

The conversion of Toluene to Benzoic acid is an important step in the production of various chemicals and materials, such as plastics, dyes, and pharmaceuticals. Benzoic acid is also used as a preservative in food and beverages.

2. What reagents are commonly used to convert Toluene to Benzoic acid?

The most commonly used reagents for this conversion are potassium permanganate (KMnO4) and concentrated sulfuric acid (H2SO4). Other options include chromic acid (H2CrO4) and nitric acid (HNO3).

3. How does the conversion from Toluene to Benzoic acid occur?

The reaction involves the oxidation of the methyl group (-CH3) in Toluene to a carboxylic acid group (-COOH), resulting in the formation of Benzoic acid. This process is often carried out in the presence of a catalyst, such as concentrated sulfuric acid, to increase the reaction rate.

4. Are there any safety considerations when using these reagents?

Yes, both potassium permanganate and concentrated sulfuric acid can be hazardous if not handled properly. It is important to wear protective equipment, such as gloves and goggles, and to follow proper handling and disposal procedures.

5. Can this conversion be carried out on a large scale?

Yes, this conversion can be scaled up for industrial production. However, it is important to carefully control the reaction conditions and to ensure proper safety measures are in place. Additionally, the purity of the reagents and the Toluene used can greatly affect the efficiency of the conversion.

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