What is the Major Product When Furan Reacts with Chloroform?

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Discussion Overview

The discussion centers on the reaction of furan with chloroform, specifically seeking to identify the major product of this reaction. The context involves the Reimer-Tiemann reaction and its comparison to the behavior of pyrrole in similar conditions.

Discussion Character

  • Homework-related, Technical explanation, Debate/contested

Main Points Raised

  • One participant suggests that the reaction resembles the Reimer-Tiemann reaction, noting that the first step involves the formation of carbene.
  • Another participant questions the assertion that carbene does not react like an electrophile.
  • A different participant clarifies that the Reimer-Tiemann reaction involves carbanion formation rather than behaving like electrophilic aromatic substitution.
  • One participant argues that the two mechanisms (carbene reactivity and electrophilic aromatic substitution) do not necessarily exclude each other.
  • Another participant inquires why furan does not react like pyrrole in the presence of carbene.
  • A participant expresses uncertainty about whether their question is problematic.
  • Another participant admits to not knowing the answer to the original question posed.

Areas of Agreement / Disagreement

Participants express differing views on the nature of carbene reactivity and its implications for the reaction of furan. There is no consensus on the major product or the underlying mechanisms at play.

Contextual Notes

Participants highlight potential differences in reactivity between furan and pyrrole, but the discussion does not resolve the implications of these differences or the specific products formed.

Titan97
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Homework Statement


What is the major product of the following reaction?
EVxC8.png

(Its CHCl3)

Homework Equations


Reimer Tieman reaction

The Attempt at a Solution


This reaction looks like the Riemer-Tiemann reaction. The only difference is the reactant. First step is the formation of carbene.
Then either of the reactions are possible:
IXMtR.png


But since carbene does not react like an electrophile, It seeks the carbon with higher electron density. That is, it attacks position 3 or 4 to form product (B).
But in case of Pyrole, the major products are:
ua4oh.jpg


Why is there a difference in the type of products?
 
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Titan97 said:
But since carbene does not react like an electrophile,
Why not?
 
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I meant reimer tiemann reaction is not like electrophilic aromatic substitution but involves carbanion formation.
 
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One doesn't exclude the other.
 
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Why doesn't Furan react like pyrrole towards carbene?
 
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Is there any problem with my question?
 
No, just that I don't know the answer.
 
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