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Cyclohexene radical isomers stability

by sludger13
Tags: cyclohexene, isomers, radical, stability
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sludger13
#1
Mar15-14, 04:07 PM
P: 75
The enthalpies of creating a cyclohexene radical isomers are:

ORTHO: 444 kJ/mol


META: 361 kJ/mol


PARA: 401 kJ/mol


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?
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sludger13
#2
Mar17-14, 12:23 PM
P: 75
Figured out, the PARA isomer has greater degree of hyperconjugation than ORTHO isomer.


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