Manisha posted an Question
December 23, 2020 • 06:27 am 30 points
  • IIT JAM
  • Chemistry (CY)

Correct order of aromaticity of pyridine, pyrrole, thiophene, furan

correct order of aromaticity of Pyridine, Pyrrole, Thiophene, Furan

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  • Manisha

    but answer is option c Pyridine>thiophene>Pyrrole>Furan..... please justify this?

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    no it should be thiophene> pyridine >pyrrole>furan

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    okay got it sir😊🤝😁

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    Priyanshu kumar Best Answer

    Aromaticity order Thiophene>pyridine > pyrrole>furan Explanation:- All of the heteroatoms will give unshared electrons to the ring to complete the aromaticity(furan,pyrrole and thiophene),and the heteroatom that will give the unshared electrons easily will be more aromatic and this depends on the electronegativity therefore thiophene is more aromatic than pyrrole and furan as the sulphur has the least electronegativity. Pyridine contains 6π electrons required for aromaticity and also it's planar and conjugated. Pyrrole and furan has 4π electrons and the lonepair of electrons on the nitrogen and oxygen participate in resonance with the ring to attain aromaticity. Therefore Pyridine is more aromatic than pyrrole and furan.

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    check this pdf for more detailed explanation

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    please ask if any doubt

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    Saurabh 1

    The aromaticity order in heterocycles(mainly pyrrole, thiophene, furan) depends on the electronegativity of the heteroatom : 0 > N > S and, therefore, the aromaticity follows the order as : Thiophene > Pyrrole > Furan. And the extra stabilization of thiophene is attributed to the expansion of valence shell of sulfur by using d-orbitals in hybridization.Well one of the factor also responsible is the resonance energy (relates to the stability of aromatic compounds), more is the resonance energy more is the aromaticity..... See the attached figure below...... Correct order is Thiophene>Pyridine>Pyrrole>Furan.....

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