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Topic: Orgo-Predicting Product question  (Read 2169 times)

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Offline rk2938

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Orgo-Predicting Product question
« on: December 19, 2013, 07:42:23 PM »
hxxps://skydrive.live.com/redir?resid=5F146673C0A3A322%212660

I don't understand how there was a abstraction of hydrogen from a vinyl location. I do get how the first product is formed. Not the second one.

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« Last Edit: December 19, 2013, 09:56:00 PM by Arkcon »
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Offline orgopete

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Re: Orgo-Predicting Product question
« Reply #1 on: December 19, 2013, 10:37:31 PM »
Reading text and from my knowledge of chemistry, this is a bona fide error in the book.
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Offline AlphaScent

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Re: Orgo-Predicting Product question
« Reply #2 on: December 23, 2013, 10:22:42 AM »
It is an allylic abstraction not an allylic abstraction.  There is no vinyl abstraction taking place.

This almost certainly done at increased temperatures.  The homolytic cleavage of the allylic bond forms a resonance stablilized radical forming the mixture of products.
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Offline AlphaScent

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Re: Orgo-Predicting Product question
« Reply #3 on: December 23, 2013, 10:25:13 AM »
God, Im an idiot.

I see it now.  Yes that answer is wrong as drawn.  But the chemistry is sound.

They would be different with respect to the labeled C13, however.

I apologize. 
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