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While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wikiWikipedia). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But a normal lone pair like that on aniline or phenol attacks by itself without delocalisation (as in Schotten Bauman reaction - wikiWikipedia). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

PS: Please also justify your answer with explanation. Even a simple counterexample will help.

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wiki). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But a normal lone pair like that on aniline or phenol attacks by itself without delocalisation (as in Schotten Bauman reaction - wiki). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

PS: Please also justify your answer with explanation.

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - Wikipedia). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But a normal lone pair like that on aniline or phenol attacks by itself without delocalisation (as in Schotten Bauman reaction - Wikipedia). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

PS: Please also justify your answer with explanation. Even a simple counterexample will help.

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source | link

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wiki). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But sa normal lone pair like that on aniline or phenol attackdattacks by itself without delocalisation (as in Schotten Bauman reaction - wiki). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

Thanks!PS: Please also justify your answer with explanation.

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wiki). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But s normal lone pair like that on aniline or phenol attackd by itself without delocalisation (as in Schotten Bauman reaction - wiki). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

Thanks!

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wiki). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But a normal lone pair like that on aniline or phenol attacks by itself without delocalisation (as in Schotten Bauman reaction - wiki). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

PS: Please also justify your answer with explanation.

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Generalizations regarding functional groups on benzene ring

While studying several organic mechanisms (high school level), I came to an interesting generalization.

I claim that negative charge on phenoxide ion first ALWAYS delocalises onto the ring and then attacks through carbon atom (like in Reimer Tienman reaction - wiki). This happens because negatively charged carbon atom is less electronegative and hence a better nucleophile than a negatively charged oxygen atom.

But s normal lone pair like that on aniline or phenol attackd by itself without delocalisation (as in Schotten Bauman reaction - wiki). This is because delocalised resonance structures have a formal positive charge on the more electronegative oxygen/nitrogen and are thus less stable.

My questions are:

  1. Does this generalization always work with regards to phenols and anilines?
  2. Is my reasoning correct for claiming these generalizations?
  3. Can this logic be extended to other functional groups on a benzene ring?

Thanks!