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Topic: Methyl acetoacetate Proton enolised  (Read 2336 times)

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Offline magnilite

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Methyl acetoacetate Proton enolised
« on: February 20, 2013, 02:00:07 PM »
Which proton in methyl acetoacetate is most likly to be enolised and what is the most stable enolic form?


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« Last Edit: February 20, 2013, 04:22:44 PM by Dan »
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Offline Dan

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Re: Methyl acetoacetate Proton enolised
« Reply #1 on: February 20, 2013, 04:24:10 PM »
You must show you have attempted the question, this is a Forum Rule.
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Offline magnilite

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Re: Methyl acetoacetate Proton enolised
« Reply #2 on: February 20, 2013, 04:48:16 PM »
 my initial thoughts one of the CH2 protons would be the first because it would form c=c bond in the middle of the molecule and be more stable
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Offline discodermolide

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Re: Methyl acetoacetate Proton enolised
« Reply #3 on: February 20, 2013, 07:07:44 PM »
Yes, it forms a C=C but you are asked for the enolate structure, can you draw the most stable enolate?
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Offline magnilite

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Re: Methyl acetoacetate Proton enolised
« Reply #4 on: February 21, 2013, 03:01:02 PM »
See attached diagram
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Offline discodermolide

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Re: Methyl acetoacetate Proton enolised
« Reply #5 on: February 21, 2013, 07:37:44 PM »
Ok, but you are missing part of the ester and a H atom.
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