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H₂C O NH₂ B₂, NaOH H₂C 98 OH When an a-hydroxy amide is treated with ry in aqueous NaOH under Hofmann rearrangement conditions, loss of CO, occurs and a chain-shortened aldehyde is formed. The mechanium involves the following steps: Base abstracts an acidic amide proton, yielding amide anion The amide anion reacts with bromine in an a-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion Rearrangement occurs to yield isocyanate H 400, ANH, Water adds to the isocyanate to yield carbamic acid . Elimination of CD, yields carbinolamine & Following proton transfer, expubion of ammonia yields the final product aldehyde Write out the mechanism on a separate sheet of paper, and then draw the structures of carbamic acid 5 and isocyanate 4 You do not have to consider stereochemistry. You do not have to explicitly draw Hatos De not include lone pairs in your answer. They will not be considered in the grading .Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthewed compound 47RR 000. Air

H₂C O NH₂ B₂, NaOH H₂C 98 OH When an a-hydroxy amide is treated with ry in aqueous NaOH under Hofmann rearrangement conditions, loss of CO, occurs and a chain-shortened aldehyde is formed. The mechanium involves the following steps: Base abstracts an acidic amide proton, yielding amide anion The amide anion reacts with bromine in an a-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion Rearrangement occurs to yield isocyanate H 400, ANH, Water adds to the isocyanate to yield carbamic acid . Elimination of CD, yields carbinolamine & Following proton transfer, expubion of ammonia yields the final product aldehyde Write out the mechanism on a separate sheet of paper, and then draw the structures of carbamic acid 5 and isocyanate 4 You do not have to consider stereochemistry. You do not have to explicitly draw Hatos De not include lone pairs in your answer. They will not be considered in the grading .Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthewed compound 47RR 000. Air

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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H₂C 0 NH₂ B₂, NaOH 98 H₂C OH When an a-hydroxy amide is treated with try in aqueous NaOH under Hofmann rearrangement conditions, loss of CO, occurs and a chain-shortened aldehyde is formed. The mechanhum involves the following steps: Base abstracts an acidic amide proton, yielding amide anion The amide anion reacts with bromine in an e-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion Rearangement occurs to yield isocyanate Water adds to the isocyanate to yield carbamic acid Elimination of CD, yields carbinolamine Following proton transfer, expubion of ammonia yields the final product aldehyde Write out the mechanism on a separate sheet of paper, and then draw the structures of carbamic acid 5 and isocyanate 4. H 400, ANH, You do not have to consider stereochemistry. You do not have to explicitly draw Hatoms De not include lone pairs in your answer. They will not be considered in the grading .Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner, Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthewed compound 47RR 000. Air
Transcribed Image Text:H₂C 0 NH₂ B₂, NaOH 98 H₂C OH When an a-hydroxy amide is treated with try in aqueous NaOH under Hofmann rearrangement conditions, loss of CO, occurs and a chain-shortened aldehyde is formed. The mechanhum involves the following steps: Base abstracts an acidic amide proton, yielding amide anion The amide anion reacts with bromine in an e-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion Rearangement occurs to yield isocyanate Water adds to the isocyanate to yield carbamic acid Elimination of CD, yields carbinolamine Following proton transfer, expubion of ammonia yields the final product aldehyde Write out the mechanism on a separate sheet of paper, and then draw the structures of carbamic acid 5 and isocyanate 4. H 400, ANH, You do not have to consider stereochemistry. You do not have to explicitly draw Hatoms De not include lone pairs in your answer. They will not be considered in the grading .Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner, Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthewed compound 47RR 000. Air
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