What is the Major Product When Furan Reacts with Chloroform?

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SUMMARY

The major product of the reaction between furan and chloroform (CHCl3) is determined through the Riemer-Tiemann reaction mechanism. In this process, carbene is generated, which preferentially attacks the carbon atoms at positions 3 or 4 of furan due to their higher electron density. Unlike pyrrole, furan's reactivity differs because carbene does not behave as a typical electrophile, leading to distinct product outcomes. Understanding this mechanism is crucial for predicting the behavior of heterocycles in organic reactions.

PREREQUISITES
  • Riemer-Tiemann reaction mechanism
  • Carbene formation and reactivity
  • Electrophilic aromatic substitution principles
  • Differences in reactivity between furan and pyrrole
NEXT STEPS
  • Study the detailed mechanism of the Riemer-Tiemann reaction
  • Explore carbene chemistry and its applications in organic synthesis
  • Investigate the reactivity of heterocycles in electrophilic reactions
  • Analyze the differences in reactivity between furan and pyrrole in various reactions
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in reaction mechanisms involving heterocycles and carbene chemistry.

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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