Which lactone is more stable in the Kiliani-Fischer synthesis of aldopentose?

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SUMMARY

In the Kiliani-Fischer synthesis of aldopentose, the formation of a γ lactone is favored over a δ lactone despite the latter being a six-membered ring, which typically suggests greater stability. The discussion highlights that the stability of lactones is influenced by factors beyond mere thermodynamics, including kinetic aspects. Reference to specific figures, such as Figure 7, Series 4 from the provided link, illustrates the underlying mechanisms affecting lactone formation.

PREREQUISITES
  • Understanding of the Kiliani-Fischer synthesis process
  • Knowledge of lactone structures and stability
  • Familiarity with thermodynamic and kinetic principles in organic chemistry
  • Ability to interpret chemical reaction mechanisms and diagrams
NEXT STEPS
  • Research the kinetic factors influencing lactone formation in organic reactions
  • Study the structural stability of different lactone types, focusing on γ and δ lactones
  • Examine the role of ring strain in lactone stability
  • Explore additional examples of lactone formation in other organic synthesis methods
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in carbohydrate chemistry and reaction mechanisms will benefit from this discussion.

utkarshakash
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Homework Statement


In the Kiliani-Fischer synthesis of aldopentose, why a γ lactone is formed when there is a possibility of δ lactone?

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The Attempt at a Solution


I think δ lactone should be more stable as it is a six-membered ring.
 
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