Reaction of furan with chloroform

In summary, the conversation discusses the formation of the major product in a reaction involving CHCl3 and the Riemer-Tiemann reaction. It is explained that the reaction involves the formation of a carbene and that the carbene will attack the carbon with higher electron density, resulting in product (B). However, in the case of pyrrole, the major products are different due to the difference in reactivity between pyrrole and furan towards carbene. The reason for this difference is not known.
  • #1
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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  • #2
Titan97 said:
But since carbene does not react like an electrophile,
Why not?
 
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  • #3
I meant reimer tiemann reaction is not like electrophilic aromatic substitution but involves carbanion formation.
 
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  • #4
One doesn't exclude the other.
 
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  • #5
Why doesn't Furan react like pyrrole towards carbene?
 
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  • #6
Is there any problem with my question?
 
  • #7
No, just that I don't know the answer.
 
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Related to Reaction of furan with chloroform

1. What is the reaction between furan and chloroform?

The reaction between furan and chloroform is an acid-catalyzed reaction that results in the formation of 1,1,1-trichlorofuran. This reaction is known as the Darzens reaction and is commonly used in organic chemistry for the synthesis of halogenated furans.

2. What are the conditions required for the reaction of furan with chloroform?

The reaction of furan with chloroform typically requires an acid catalyst, such as hydrochloric acid or sulfuric acid, and a solvent such as dichloromethane. The reaction is usually carried out at room temperature or slightly elevated temperatures.

3. What is the mechanism of the reaction between furan and chloroform?

The reaction between furan and chloroform follows a two-step mechanism. In the first step, the acid catalyst protonates the carbonyl group of furan, making it more electrophilic. In the second step, the chloroform attacks the electrophilic carbon, leading to the formation of 1,1,1-trichlorofuran.

4. What are the applications of the reaction of furan with chloroform?

The reaction of furan with chloroform has several applications in organic synthesis. It is commonly used for the preparation of various halogenated furans, which can be used as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

5. Are there any safety concerns associated with the reaction of furan with chloroform?

Yes, there are some safety concerns associated with the reaction of furan with chloroform. Chloroform is a toxic and potentially carcinogenic chemical, so proper precautions should be taken when handling it. Additionally, the reaction may produce hydrogen chloride gas, which is corrosive and can cause respiratory irritation. Therefore, it is important to conduct the reaction in a well-ventilated area and wear appropriate personal protective equipment.

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