Isomers of Benzene
Journal:
Journal of Chemical Education
Year:
1994
Volume:
71
Pages:
222-224
URL for article at publisher's site:
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Organic Chemistry 2 on iTunesU
Description:
This is a set of lecture videos for organic chemistry 2. The videos are recorded tablet style and not in front of a class. They are available through iTunesU. To experience all of the content, run the iTunesU app on an iPad. The videos can be watched on any computer that runs iTunes.
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Why is 1,4-cyclohexadiene stable?
Abstract:
Why is 1,4-cyclohexadiene stabilized? Using qualitative perturbation theory to teach conjugation
Six-carbon polyenes display quite regular properties, when one compares their stabilities using hydrogenation enthalpies. Each double bond in a conjugated system is worth about 10 kJ/mol in resonance energy, and non-conjugated dienes show no resonance energy. Cyclohexadienes are puzzling: 1,3-cyclohexadiene is less stable, and 1,4-cyclohexadiene is more stable, than corresponding open-chain dienes. Qualitative molecular orbital perturbation theory can be used to explain these anomalies.
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