What is the Major Product When Furan Reacts with Chloroform?

AI Thread Summary
The major product of the reaction between furan and chloroform is determined through the Riemer-Tiemann reaction mechanism, which involves carbene formation. In this context, the carbene targets the carbon atoms with higher electron density, specifically positions 3 or 4 of furan, leading to product formation. The discussion highlights the difference in reactivity between furan and pyrrole, noting that furan does not behave like pyrrole in this reaction due to its electronic structure. This raises questions about the nature of carbene reactivity and the formation of carbanions. Overall, the inquiry emphasizes the complexities of aromatic reactivity in different heterocycles.
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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