prob_solving_ses - fine on the exam! Working through these...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco Optional Problem Solving Session Monday, December 1st, 12–1PM 1. Please provide a detailed mechanism for each of the following transformations. Do not concern yourself with stereochemistry. a) 1. LDA O O 2. O Me OMe Me MeO 3. H 2 O OMe CO 2 Me b) Me Me H 3 O + O HO c) AcO O O AcO H + d) H O O CO 2 Me Lewis Acid H (LA) CO 2 Me MeO 2 C CO 2 Me These mechanisms are fairly complicated. In other words, if you can do these, you will be
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Unformatted text preview: fine on the exam! Working through these problems will help you to develop a good strategy for tackling simpler problems in a reasonable time frame. It might help you to follow some of the following steps to get started. 1. Number your carbons. (Which carbon ends up where?) 2. Make a list of the bonds that are broken and formed in the reaction. 3. If you can't decide where to begin, start by working backwards. 4. Look for familiar reactions, rearrangements, etc....
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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