November 27, 2024, 11:47:42 AM
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Topic: mechanism creating cis 2,6-dimethylhexanone from trans 2,6-dimethylhexanone  (Read 1759 times)

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Offline epsu1025

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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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« Last Edit: November 12, 2014, 05:08:02 PM by Dan »

Offline mjc123

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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?

Offline Altered State

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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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