Hi,

We did an experiment in lab and our professor asked us why we used acetic acid as our oxidizing agent

NaOCl + CH3COOH --> HOCl + CH3COO- Na+

for the above reaction?

I'm thinking it has to do with the fact that it is a relatively weak acid and can be reversed if needed?

Am I like totally off?

Thanks for any help!
Best,
Mandy

I don't see any oxidizing or reducing going on. What you have written is a double displacement reaction (or double replacement reaction).

You do have an oxidizing agent in the reaction (NaOCl) BUT it isn't oxidizing anything.

I am not aware of acetic acid being used as an oxidising agent. The peracid is much more common.

So

NaOCl + CH3COOH --> NaCl + CH3COOOH

and the acetic acid is the reducing agent.

Formic acid is used as a reducing agent in Eschweiler-Clarke Methylation.

Hi Mandy,

Great question! The choice of acetic acid as an oxidizing agent in your experiment is indeed based on its properties and the specific requirements of your reaction.

Acetic acid (CH3COOH) is a weak acid, and in the presence of a strong base or a high pH environment, it can be easily deprotonated to form acetate ions (CH3COO-). This means that acetic acid can act as a source of acetate ions, which can participate in various chemical reactions.

In the reaction you provided, acetic acid (CH3COOH) reacts with sodium hypochlorite (NaOCl) to yield hypochlorous acid (HOCl) and acetate ions (Ch3COO-). This reaction is an oxidation-reduction (redox) reaction, where acetic acid is acting as an oxidizing agent.

One possible reason why acetic acid was chosen as the oxidizing agent is that it can provide a mild and controlled oxidation environment. As a weak acid, acetic acid is less likely to produce highly reactive and aggressive oxidizing species that could lead to undesired reactions or side products. This makes acetic acid suitable for specific oxidation reactions that require a more gentle and controllable approach.

Furthermore, acetic acid can be easily reversed if needed. Being a weak acid, the acidity of acetic acid can be neutralized by adding a base or adjusting the pH of the solution, allowing for the reaction to be reversed if desired. This reversibility can be beneficial in cases where the reaction needs to be controlled or in situations where any excess acetic acid needs to be removed or recovered.

So, your intuition is correct! The choice of acetic acid as the oxidizing agent in your experiment is likely due to its relatively mild nature, controllability, and reversibility.

I hope this explanation helps! Let me know if you have any further questions.