Transformers

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Jul 12, 2007
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This is a pretty specific question, but:

In the beckmann rearrangement in which you have the OXIME --Acid--> AMIDE...

1.) In the oxime in which there are two R groups (R1 and R2 lets assume) attached to sp2 carbon double bonded with the nitrogen, what factors dictate which R group will attack the nitrogen once H2O leaves to form the nitrile. I am guessing its something thats very nucleophilic, yet not sterically hindering.

So an oxime that has 2 R groups (a methyl and tertbutyl), would the methyl group attack the nitrogen once water displaces.

....I realize this is specific so I hope you guys could refer to the mechanism of the Beckmann (http://en.wikipedia.org/wiki/Beckmann_rearrangement)

Thanks.
 

Hemichordate

Peds
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May 5, 2008
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And if it is, everything you need to know the question will probably be in the passage.