Week_6.2_PurpleBook_Answers

Week_6.2_PurpleBook_Answers - 147 Basic Aldol and Claisen...

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O H H O O H 2 CO MeO O O OMe O H 2 O H H O O O H OH O H H O H O H H (thermodynamic enolate) Basic Aldol and Claisen Mechanisms 1. Predict the product, and provide a curved-arrow mechanism for each of the following transformations. MeO O + O OMe MeO O LDA (0.9 equiv.) –78°C O H 2 O work-up OMe MeO O H—OH :NR 2 (thisisLDA) O :OMe H H—OMe MeO O :OMe Aldol Addition O Aldol Condensation :OMe Claisen (or Dieckmann) Condensation H :OMe H H O O OH NaOMe NaOMe Week 6 147
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O H O O H H O O OH More Aldol and Claisen Mechanisms H O 1. Provide curved-arrow mechanisms for the following transformations: H H O O O O H—OH O H O Why deprotonate at that carbon? Any other possibilities would give less stable 4-membered ring. 5- and 6-membered rings are nearly always preferred. H H OH O H H H O Acid-catalyzed Aldol addition! H H OH H OH NaOH H 3 O + :OH :OH H + :OH 2 H + :OH 2 Week 6 148
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OH O O O O O O O O O O O OH H O
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Week_6.2_PurpleBook_Answers - 147 Basic Aldol and Claisen...

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