This needs a little background so I will be showing you a question from one of my Organic Chemistry problem books:-

Now, the book shows the answer as Option (c) which is Paracetamol. I tried to work out the mechanism and I was pondering over the fact that the products left in the reaction are Paracetamol and Ethanoic acid . Now Paracetamol contains an -OH(Hydroxy group) and O(Oxygen) atom can easily aquire positive charge by mesomeric stabilisation and attack Ethanoic acid to further form ester (as in Option (a)) . Can someone please help me out ?

  • $\begingroup$ Acetates of phenol are pretty as good acylating agents and don't survive aqueous base work up $\endgroup$ – Waylander Dec 27 '20 at 13:28
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    $\begingroup$ There is no stoichiometry in your reaction. If Ac2O is in excess, then A is the answer and Waylander's comment applies to form C. If the stoichiometry is 1:1, then C>>B. Heating this mixture, possibly neat, would convert B into C. Can you figure out why? $\endgroup$ – user55119 Dec 27 '20 at 15:20
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    $\begingroup$ There are other underlying issues with your description. Firstly, what do you mean by oxygen "acquiring a positive charge", and secondly, why should that be of any help with esterification? If your oxygen is acting as a nucleophile, you probably don't want it to be positively charged. $\endgroup$ – orthocresol Dec 27 '20 at 18:06

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