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Beckmann rearrangement

Mechanism

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Dave M. | Most Experienced, Helpful Organic Chemistry Tutor Available AnywhereMost Experienced, Helpful Organic Chemis...
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The Beckmann Rearrangement is a ring expansion rearrangement of an oxime =N-OH on a ring. It is a facile reaction that is able to produce even 7-membered ring lactams.
 
If you start with a cycloalkanone and add hydroxylamine, you get an imine with a hydroxyl group on it (an oxide). Tosylation or even acid catalysis is sufficient to cause the adjacent α-carbon to migrate to the iminium Nitrogen atom, displacing the -OH group and increasing the size of the ring by one. Attack by water, either in the medium or upon workup, gives the enamine which tautomerizes to the amide. Inside a ring, the amide make the molecule a lactam.  
 
It is very versatile as the resulting lactam (cyclic amide) can be reduced to its corresponding amine. 
Kenneth S. | Algebra/Trig/Precalculus/Calculus Instructor Can Be Your TutorAlgebra/Trig/Precalculus/Calculus Instru...
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Terse.
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