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Topic: Styrene Radicals Stability  (Read 5107 times)

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Offline mizna.z

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Styrene Radicals Stability
« on: July 29, 2009, 12:48:20 PM »
Two different radicals can be produced when an initiator radical adds to styrene- a primary radical and a secondary radical.
Would the secondary radical be more stable due to something called hyperconjugation?
If so, then why do they http://www.meta-synthesis.com/webbook/14_radical/radical.html show it as a primary one?
(scroll to the near bottom of the link above).-see attached pic

Offline orgopete

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Re: Styrene Radicals Stability
« Reply #1 on: August 02, 2009, 02:46:50 AM »
You are correct about the secondary (and benzylic) radical being more stable. I believe the Chemogenesis reference is in error.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline ufalynn88

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Re: Styrene Radicals Stability
« Reply #2 on: August 10, 2009, 12:21:14 AM »
a secondary radical would definitely be more stable than a primary...and tertiary (then allylic, and then benzylic even more stable than that...)...a carbon with a radical present is highly unstable and electrophilic...the presence of neighboring carbons push some electron density onto the radical...thus, the more carbons donating this density in, the more stable =)

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