Week 5-July 27

Week 5-July 27 - Week 5 July 27, 2011 The Claisen...

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Week 5 July 27, 2011 The Claisen Condensation: Another Cool Reaction Provide a complete curved-arrow mechanism for the following reaction: OEt O NaOEt OEt O O H + workup OEt O O K eq ! 24 Explain why the following attempted Claisen condensation does not work, and provide a curved-arrow mechanism for the reverse reaction: OEt O NaOEt OEt O O eq << 1 Reading : Section 22.5 90
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Week 5 July 27, 2011 Intramolecular and “Crossed” Claisen Condensations Provide curved-arrow mechanisms for the following reactions: O O OMe MeO OMe O O 1. NaOMe 2. H + workup OEt O + EtO OEt O (excess) O OEt O OEt 1. NaOEt 2. H + workup O + OEt O (excess) 1. NaOEt 2. H + workup O O Reading : Section 22.5 91
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July 27, 2011 Hydrolysis and Decarboxylation of ! -Keto Esters Provide a complete curved-arrow mechanism for the following transformation: O O OMe NaOH H + heat O Why is the ! -ketone (or other ! -carbonyl group) essential for this reaction? Reading
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Week 5-July 27 - Week 5 July 27, 2011 The Claisen...

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