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In the reaction of phenol with acetyl chloride the oxygen of the phenol attacks the acetyl chloride. In Bakelite formation we know that pi electrons attack the carbonyl carbon of formaldehyde.My question is shouldn't the oxygen atom of phenol attack the formalaldehyde just as in the reaction of phenol with acetyl chloride?

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  • $\begingroup$ I'm having a little trouble understanding what you're trying to ask. Could you try separating this into two sentences? I'd do it, but I don't want to misinterpret. $\endgroup$ – ringo Feb 16 '16 at 6:14
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  1. C-acylation : acylating agent (acyl chloride or anhydride) and $\ce{AlCl3}$

  2. O-acylation : acylating agent (acyl chloride or anhydride).This is the one which you have talked about in the question.

Since the formation of bakelite is by Lederer Manasse reaction which proceeds through electrophilic aromatic substitution on phenol, its path is similar to that in C- acylation and not O-acylation. Hence, the polymerisation of phenol and formaldehyde takes place either from two places:

  • For para substitution end:

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  • For ortho substitution end:

enter image description here

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    $\begingroup$ Please cite the sources for your pictures, and preferably text. $\endgroup$ – M.A.R. Jun 12 '16 at 18:27
  • $\begingroup$ it.wikipedia.org/wiki/Reazione_di_Lederer-Manasse I have learnt about reactions that proceed through EAS (hence the above reactions: Lederer Manasse and Friedel Craft Acylation) hence the text is my original passed down by my professor. $\endgroup$ – Piyush Mishra Jun 13 '16 at 7:19

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