Week 6-August 2

Week 6-August 2 - Week 6 August 2, 2011 1,2-Alkyl Migration...

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Week 6 August 2, 2011 1,2-Alkyl Migration to Nitrogen There are three similar reactions in which an alkyl group undergoes a migration (shift) onto a nitrogen atom. These reactions are: The Beckmann Rearrangement : H 2 NOH pH 5 O N OH H + HN O The Curtius Rearrangement: Cl O NaN 3 N 3 O unstable N C O ROH H N O OR The Hofmann Rearrangement: NH 2 O Br 2 , OH NH 2 What is the common feature of the mechanisms of all three of these reactions? Reading : Section 23.11 134
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Week 6 August 2, 2011 Beckmann and Curtius Rearrangements Show the mechanism of the Beckmann Rearrangement. H 2 NOH pH 5 O N OH H + HN O Show the mechanism of the Curtius Rearrangement. Cl O NaN 3 N 3 O unstable N C O ROH H N O OR Reading : Section 23.11 135
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August 2, 2011 Hofmann Rearrang e ment Show the mechanism of the Hofmann Rearrangement. NH 2 O Br 2 , OH NH 2 Why might the Hofmann rearrangement be helpful in carrying out the following synthesis? Br
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Week 6-August 2 - Week 6 August 2, 2011 1,2-Alkyl Migration...

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