Acetylation- acetic acid or acetic anhydride

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In summary, the conversation is about an experiment with p-acetylaminotoluene and the question of which chemical was the acetylating species. The individual used both acetic acid and acetic anhydride but is unsure which one was responsible for the high yield. They are seeking advice and clarification on the role of each chemical in the reaction.
  • #1
Taryn
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I did an experiment in one of the labs and I have a question I need to figure out.
The experiment was the porduction of p-acetylaminotoluene, from p-toluidine.
My question is we used acetic acid and acetic anhydride, but which is the acetyalting species.
I thought of looking at the structures of them but that kinda just confused me more.
I know that acetic anhydride is used to acetylate secondary and primary alcohols sometimes, but it gives a lower yield.
I got quite a high yield so I thought that the acetic acid might have been the acetylating species.

If anyone could just point me in the right direction that would be gr8. I am goin to ask my demonstrator today but any help would still be much appreciated.
 
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  • #2
Have a look at the quantities of both chemicals you used, if that doesn't point you in the right direction post all the numbers here and I'll have a look at them for you.
 
  • #3
I used 4ml of acetic acid and 6ml of acetic anhydride.
I don't know how knowing how much I put in shows which is the acetylating species?
 
  • #4
acetic acid is an acid and toluidine is an amine base. What happens when you combine an acid with a base?
 

1. What is the purpose of acetylation using acetic acid or acetic anhydride?

Acetylation is a chemical process in which an acetyl group (CH3CO-) is added to a molecule. Acetic acid and acetic anhydride are commonly used as acetylating agents in this process. The purpose of acetylation is to modify the properties of a molecule, such as increasing its stability, solubility, or reactivity.

2. How does acetylation using acetic acid or acetic anhydride differ from other forms of acetylation?

Acetic acid and acetic anhydride are both strong acetylating agents, meaning they are effective at transferring an acetyl group to a molecule. This differs from other forms of acetylation, such as enzymatic acetylation, which requires specific enzymes to catalyze the reaction.

3. What types of molecules can be acetylated using acetic acid or acetic anhydride?

Acetic acid and acetic anhydride can be used to acetylate a wide range of molecules, including proteins, amino acids, sugars, and small organic molecules. However, the reactivity and selectivity of the acetylating agent may vary depending on the specific molecule being acetylated.

4. What are the potential risks associated with working with acetic acid or acetic anhydride?

Both acetic acid and acetic anhydride are corrosive and can cause skin and eye irritation, so proper safety precautions should be taken when handling these chemicals. In addition, acetic anhydride can react violently with water, making it important to handle it with care and in a well-ventilated area.

5. Can acetylation using acetic acid or acetic anhydride be reversed?

In most cases, acetylation is a permanent modification of a molecule and cannot be easily reversed. However, it is possible to remove the acetyl group using chemical or enzymatic methods. This process is known as deacetylation.

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