Register to reply

Cyclohexene radical isomers stability

by sludger13
Tags: cyclohexene, isomers, radical, stability
Share this thread:
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?
Attached Images
Phys.Org News Partner Chemistry news on
Video: How did life on Earth begin?
Now you can turn your inkjet printer into a chemistry lab and use it to diagnose diabetes
Advanced molecular 'sieves' could be used for carbon capture
Mar17-14, 12:23 PM
P: 75
Figured out, the PARA isomer has greater degree of hyperconjugation than ORTHO isomer.

Register to reply

Related Discussions
Delocalized electron in cyclohexene? Chemistry 2
Relative stability of allyl radical Chemistry 2
Isomers: Geometric and Diastereometric Isomers Biology, Chemistry & Other Homework 2
Cyclohexene and toluene + sulfuric acid Chemistry 1