Cyclohexene radical isomers stability

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: 657
  • o.jpg
    o.jpg
    921 bytes · Views: 732
  • p.jpg
    p.jpg
    1 KB · Views: 803
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