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Why electrophilic substitution reaction occur at 2 and 5 position in furan?

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∙ 11y ago

Updated: 4/28/2022

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Q: Why electrophilic substitution reaction occur at 2 and 5 position in furan?

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Why the electrophilic substitution going to occur in furon thiophene and pyrole?

Electrophilic substitution occurs in furan, thiophene, and pyrrole because these compounds have a lone pair of electrons on the heteroatom (oxygen, sulfur, or nitrogen), making them nucleophilic and reactive towards electrophiles. The aromaticity of these compounds is also maintained during the substitution reaction, making them favorable candidates for electrophilic substitution.

Why furan do not show nucleophilic subtitution reaction?

Furan does not typically undergo nucleophilic substitution reactions because of its aromatic nature, which offers stability due to delocalization of the pi electrons in the ring. This makes furan less reactive towards nucleophilic attack compared to non-aromatic compounds.

Why do 5-membered ring aromatic heterocycles pyrrole and furan undergo electrophilic substitution more rapidly than benzene while 6-membered ring heterocycles like pyridine are less reactive than Benz?

5-membered ring heterocycles like pyrrole and furan have greater reactivity due to their higher electron density compared to benzene, making them more susceptible to attack by electrophiles. In contrast, the nitrogen atom in pyridine stabilizes the ring by delocalizing the lone pair of electrons, reducing its reactivity towards electrophilic substitution reactions.

What is the reaction of furan with maleic anhydride?

When furan reacts with maleic anhydride, it forms a Diels-Alder adduct called endo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. This reaction is a type of cycloaddition reaction that involves the formation of a new ring structure.

How is furan produced from pentose?

Furan can be produced from pentose through a dehydration reaction. When a pentose, such as ribose or xylose, undergoes dehydration in the presence of acid catalysis, it can form furfural, which can further react to produce furan. This process can be used in biomass conversion techniques to produce furan derivatives for various industrial applications.

Why furan is more reactive than pyrrole and thiophene?

Furan is more reactive than pyrrole and thiophene because the oxygen atom in furan is more electronegative than the nitrogen in pyrrole and sulfur in thiophene. This increases the electron density on the carbon atom in furan, making it more susceptible to nucleophilic attack. Additionally, furan has a larger π-system due to the presence of the oxygen atom, allowing for greater delocalization of electrons and stabilization of reaction intermediates.

Why Furan turns brown on exposure to air?

Furan is prone to oxidation reactions in the presence of air. This oxidation process causes the molecular structure of furan to change, leading to the formation of brown-colored compounds as byproducts. This is why furan turns brown when exposed to air.

Why is furan insoluble in ether?

Furan is insoluble in ether because furan is a polar compound and ether is a nonpolar solvent. Like dissolves like, so the polarity mismatch between furan and ether prevents them from forming a homogeneous solution.

Why pyrole is more basic then furan?

Pyrrol has a lone pair of electrons on the nitrogen atom, which is more available for donation compared to the lone pair on oxygen in furan. This makes pyrrole more basic than furan.

If the Diels-Alder reaction between dimethylmaleic anhydride and furan had worked would cantharidin have been formed?

Yes, if the Diels-Alder reaction between dimethylmaleic anhydride and furan had been successful, cantharidin could have been formed. Cantharidin is a natural product that can be synthesized through Diels-Alder reactions involving maleic anhydride derivatives and dienes like furan.

Is furan a polar compound?

Yes, furan is a polar compound due to the presence of polar covalent bonds in the molecule. The oxygen atom in furan is more electronegative than carbon, leading to an uneven distribution of electron density and creating a polar molecule.

What is basicity of furan?

furan though has a lone pair of electron which is not delocalised but due to high electronegetivity of oxygen it is not a available for donation hence has weak basic proerty

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