Chemistry: The Molecular Science
5th Edition
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:John W. Moore, Conrad L. Stanitski
Chapter20: Chemistry Of Selected Transition Elements And Coordination Compounds
Section: Chapter Questions
Problem 58QRT
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Question
When an α-hydroxy amide is treated with Br2 in aqueous NaOH under Hofmann rearrangement conditions, loss of CO2 occurs and a chain-shortened aldehyde is formed. The mechanism involves the following steps:
Base abstracts an acidic amide proton, yielding amide anion 1;
The amide anion reacts with bromine in an α-substitution reaction to give N-bromoamide 2.
Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion 3;
Rearrangement occurs to yield isocyanate 4;
Water adds to the isocyanate to yield carbamic acid 5;
Elimination of CO2 yields carbinolamine 6;
Following proton transfer, expulsion of ammonia yields the final product aldehyde.
Write out the mechanism
and then draw the structures of bromoamide anion 3 and amide anion 1.
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