Order of bond energy in furan, pyrolle and thiophene

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SUMMARY

The order of bond energy for heterolytic cleavage of the C-Br bond in furan, pyrrole, and thiophene is determined by the electronegativity of the heteroatoms involved. Contrary to initial assumptions, the bond energy is highest in thiophene, followed by pyrrole, and lowest in furan. This is due to the stabilizing effects of resonance and the varying electronegativities of sulfur, nitrogen, and oxygen. Specifically, the resonance stabilization in thiophene outweighs the electronegativity effects, leading to a lower bond energy requirement for cleavage.

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  • Understanding of heterolytic cleavage in organic chemistry
  • Knowledge of resonance structures and their impact on stability
  • Familiarity with electronegativity trends among elements
  • Basic concepts of carbocation stability
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  • Research the concept of resonance stabilization in heterocycles
  • Study the electronegativity differences between sulfur, nitrogen, and oxygen
  • Explore the mechanisms of heterolytic cleavage in organic reactions
  • Investigate the stability of carbocations in various organic compounds
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Krushnaraj Pandya
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Homework Statement


A bromo-methyl group is attached adjacent to the N,O and S atoms respectively in furan, pyrolle and thiophene, find correct order of bond energy required for heterolytic cleavage of CBr bond forming carbocation

2. The attempt at a solution
Lone pairs participate in resonance in all three, so I thought the only different thing is the elctronegativity of the atoms. Since Oxygen>Nitrogen>Sulphur in EN furan would be most unstable since it'd try to pull electrons from the already positive carbon so its bond energy should be highest, then pyrolle's then thiophene but this is incorrect. I'd appreciate some help, thank you
 
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