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Topic: keto-enol stability  (Read 6606 times)

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Offline refid

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keto-enol stability
« on: May 11, 2007, 12:11:50 AM »



Im wondering which keto-enol would predominate..my first guess would be the first one since there isn't steric hindrance to deprotonate (like in the second one).. but looking at the cation, the second one would have a stable intermediate allowing the double to move.

So my final guess would be the Second ketone



Offline alphahydroxy

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Re: keto-enol stability
« Reply #1 on: May 11, 2007, 06:16:00 AM »
I really don't follow what you're asking here... Are you asking which process is going to occur faster? i.e. whether phenol or para-maethyl phenol is formed more quickly under these conditions?

Offline refid

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Re: keto-enol stability
« Reply #2 on: May 11, 2007, 11:57:59 AM »
2,5-cyclohexadienone vs. 4-methyl-2,5-cyclohexadienone
In two solutions, which one would have a higher enol content?


My guess its 4-methyl-2,5-cyclohexadienone since the methyl group stablizes the cation.


Offline moussa

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Re: keto-enol stability
« Reply #3 on: May 11, 2007, 04:09:10 PM »
both reactions gonna occur but the second is faster having a methyl group that is a charge intensifier ==> it would stabilize the cation and inhances the formation
earth is larger than a molecule

Offline refid

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Re: keto-enol stability
« Reply #4 on: May 11, 2007, 09:02:06 PM »
both reactions gonna occur but the second is faster having a methyl group that is a charge intensifier ==> it would stabilize the cation and inhances the formation

i guess my guess is right

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