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First mechanism is the one taught in lecture, and I wondered why the electrons from carbonyl Oxygen wouldn't react with thionyl chloride.
So I tried to draw a second mechanism as much as I could but it won't produce the same product.

So my question is:

Is nucleophilic attack from carbonyl Oxygen less likely. If so, why?
If not, where did I go wrong?

  • $\begingroup$ Well, $sp^2$ electrons are less nucleophilic because they are closer to the nucleus. But those oxygens are essentially equivalent because the two tautomers are the same. The first "mechanism" you show isn't really a mechanism, by the way. It's missing several steps. $\endgroup$ Apr 5, 2016 at 8:10
  • $\begingroup$ by the way, why is this question duplicate? it's true I asked about Acid chloride formation twice but these are not the same question as far as i'm concerned. $\endgroup$
    – NK Yu
    Apr 6, 2016 at 2:55
  • $\begingroup$ I'm inclined to agree that these are different questions. $\endgroup$ Apr 6, 2016 at 4:58


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