Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: billsauce on May 01, 2013, 01:54:17 AM
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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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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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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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The one in which the oxygen is bearing the negative charge is more stable..!