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Acetylation- acetic acid or acetic anhydride

  1. Jun 7, 2007 #1
    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.
  2. jcsd
  3. Jun 8, 2007 #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.
  4. Jun 12, 2007 #3
    I used 4ml of acetic acid and 6ml of acetic anhydride.
    I dont know how knowing how much I put in shows which is the acetylating species?
  5. Jun 12, 2007 #4


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    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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