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Question: Answered & Verified by Expert
In the context of the rearrangement of an oxime of a ketone to an amide (represented below)

Which of the following statement is/are correct?
ChemistryCarboxylic Acid DerivativesJEE Main
Options:
  • A It is the cis hydrocarbon radical \( (R) \) with respect to the \( \mathrm{OH} \) group that migrates
  • B The group that migrates never gets completely detached from the remainder of the molecule during the transformation
  • C The rearrangement is intermolecular
  • D None of the above
Solution:
2662 Upvotes Verified Answer
The correct answer is: The group that migrates never gets completely detached from the remainder of the molecule during the transformation

This reaction is an example of Backmann rearrangement. It is an intramolecular rearrangement.  Beckmann Rearrangement is a reaction where oxime is changed to an amide. Beckmann rearrangement consists of an alkyl group migration, that is anti-periplanar to the expulsion of a leaving group and form nitrilium ion. This is followed by attack of water molecule to an imidate and then tautomerization to the amide:

Beckmann rearrangement - Wikipedia

 

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