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mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone
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Topic: mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone (Read 1757 times)
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epsu1025
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mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone
«
on:
November 09, 2014, 02:32:04 PM »
For a homework I am asked to propose a mechanism for this reaction
I think if I know how to get started I would be able to do this, but I am not sure where to start.
Any advice would be greatly appreciated!
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. Dan
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Last Edit: November 12, 2014, 05:08:02 PM by Dan
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mjc123
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Re: mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone
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Reply #1 on:
November 11, 2014, 05:08:26 AM »
For a start, it's cyclohexanone, not hexanone.
It looks like a reversible acid-catalysed enolisation resulting in formation of the thermodynamic product.
Why do you think the cis isomer is more stable than the trans?
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Altered State
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Re: mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone
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Reply #2 on:
November 12, 2014, 11:28:50 AM »
Formation of enol under acidic conditions and then regeneration of the ketone seems to be they way to go.
As mjc123 stated, thermodynamic product will form. Why? Draw chair conformations of both diasteroisomers
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mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone