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Topic: which pair of enolate ions is more stable?  (Read 1972 times)

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Offline billsauce

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which pair of enolate ions is more stable?
« on: May 01, 2013, 01:54:17 AM »
which pair of enolate ions is more stable? I think it is the one with the c=o bond and the lone pair on the CH group, because the c=o bond is more stable than having an O- group. But I am not fully sold on this because I also know a c=c bond is stable. Which one is more stable?
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Offline billsauce

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Re: which pair of enolate ions is more stable?
« Reply #1 on: May 01, 2013, 01:59:26 AM »
also keto tautomers are more stable than enol, so this would make sense to me that the one with the c=o bond is more stable?
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Offline Dan

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Re: which pair of enolate ions is more stable?
« Reply #2 on: May 01, 2013, 02:42:11 AM »
Negative charge is generally more stable on a more electronegative atom; the enolate form is generally considered the major resonance contributor compared to the carbanion.

In this case I would also consider ring strain. The most stable enolate from that ketone is probably not the one you have drawn.
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Offline betterbesafehero

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Re: which pair of enolate ions is more stable?
« Reply #3 on: May 01, 2013, 01:12:38 PM »
The one in which the oxygen is bearing the negative charge is more stable..!
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