Acetylation- acetic acid or acetic anhydride

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SUMMARY

The discussion centers on the acetylation process in the synthesis of p-acetylaminotoluene from p-toluidine, specifically questioning whether acetic acid or acetic anhydride serves as the acetylating agent. The participant noted a higher yield in their experiment, leading to speculation that acetic acid may be the active acetylating species. It was also mentioned that acetic anhydride is typically used for acetylation but can yield lower results in certain reactions. The quantities used in the experiment were 4ml of acetic acid and 6ml of acetic anhydride.

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  • Understanding of acetylation reactions in organic chemistry
  • Familiarity with the structures and properties of acetic acid and acetic anhydride
  • Knowledge of reaction yields and factors affecting them
  • Basic principles of acid-base chemistry
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  • Research the mechanisms of acetylation involving acetic acid and acetic anhydride
  • Study the impact of reactant quantities on yield in organic synthesis
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  • Investigate the acid-base reaction dynamics between amines and carboxylic acids
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Chemistry students, organic chemists, and laboratory technicians involved in synthesis and reaction optimization will benefit from this discussion.

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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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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.
 
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?
 
acetic acid is an acid and toluidine is an amine base. What happens when you combine an acid with a base?
 

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