Sherlock Holmium
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Alpha halogenation
Just a quick question: Does alpha halogenation of a ketone occur on the least or most substituted carbon?
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HeYBrO
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just a quick note: spoon feeding is not permited here
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solo
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.....maybe you can read about it.....solo
https://chemistry.stackexchange.com/questions/23500/regiosel...
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Assured Fish
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Lets turn this thread into something more useful.
I have a question pretaining to enols.
I ask because i have never found an example of this being done before despite my research.
Would it be possible to reflux a ketone in an excess of say HBr to form a halo alkene.
The following is the reaction i wish to accomplish.
I suppose this would really be a question of, would the HBr attack the alkene or would it rather attack the hydronium leaving group.
Then i guess the other issue is under the harsh condition of refluxing there may be other side reactions involving HBr adding across the double bond
of 1,2 dibromopropene.
Perhaps a similar reaction could be accomplished using a much stronger halogenating agent such as thionyl halide or phosphorous trihalide which would
perhaps mitigate the harsh conditions required for a hydrogen halide to accomplish the same task.
Any input would be appreciated?
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HeYBrO
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I think you should draw out the full mechanism of what you are proposing
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Assured Fish
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New thread to go with it too i reckon.
[Edited on 17-6-2018 by Assured Fish]
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