Cyclohexene radical isomers stability

Click For Summary
SUMMARY

The stability of cyclohexene radical isomers is determined by their enthalpies of formation: ORTHO at 444 kJ/mol, PARA at 401 kJ/mol, and META at 361 kJ/mol. The META isomer is the most stable due to the participation of the meta-carbon in multiple bonds, while the ORTHO isomer is the least stable due to lower hyperconjugation compared to the PARA isomer. The PARA isomer benefits from a greater degree of hyperconjugation, enhancing its stability over the ORTHO isomer.

PREREQUISITES
  • Understanding of radical chemistry
  • Knowledge of enthalpy and thermodynamic stability
  • Familiarity with hyperconjugation concepts
  • Basic grasp of isomerism in organic compounds
NEXT STEPS
  • Research the role of hyperconjugation in radical stability
  • Study the mechanisms of radical addition reactions
  • Explore the properties of cyclohexene and its derivatives
  • Investigate computational methods for calculating enthalpies of formation
USEFUL FOR

Chemists, organic chemistry students, and researchers focusing on radical mechanisms and isomer stability in organic compounds.

sludger13
Messages
83
Reaction score
0
The enthalpies of creating a cyclohexene radical isomers are:

ORTHO: 444 kJ/mol
attachment.php?attachmentid=67679&stc=1&d=1394915706.jpg


META: 361 kJ/mol
attachment.php?attachmentid=67678&stc=1&d=1394915706.jpg


PARA: 401 kJ/mol
attachment.php?attachmentid=67680&stc=1&d=1394915706.jpg


The meta-isomer is most stable (that is the reason for the formation of meta product in radical addition). Para/meta isomers energies seem obvious - both carbons are equivalent, only the meta-carbon participates in multiple bond, para-carbon doesn't.
I can't see why the ORTHO-isomer is the least stable one. The (.CR3) radical should rather be more stable than (.CHR2). What do you think?
 

Attachments

  • m.jpg
    m.jpg
    916 bytes · Views: 628
  • o.jpg
    o.jpg
    921 bytes · Views: 712
  • p.jpg
    p.jpg
    1 KB · Views: 782
Chemistry news on Phys.org
Figured out, the PARA isomer has greater degree of hyperconjugation than ORTHO isomer.
 

Similar threads

  • · Replies 2 ·
Replies
2
Views
8K
  • · Replies 11 ·
Replies
11
Views
11K