ps6 (1) - for each transformation. a) O OH OH-, HO H 3 O +...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco Problem Set 6 Due: Monday, 11/24/03 at 4 PM 1. Please provide a mechanism for each of the following transformations. O O CH 3 O O a) 1 equiv. MeO MeOH b) O O Br 2 Br AcOH 2. Please provide the products of the following reactions and indicate whether or not you expect the reaction to be selective. If you expect more than one product, show them all. H CH 3 O O 2 O 2. a) 1. NaOH, H b) O 1 equiv. Br 2 Ph CH 3 NaOH c) O O 1. NaOCH 3 CH 3 H 3 C OCH 3 2. H 3 O + H 3 C d) O O 1. NaOH, H 2 O CH 3 H 2. H 3 C H 3 C
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3. Please provide a mechanism for the following transformation. O O NaOMe CH 3 H 2 C O 4. Please provide syntheses of the indicated compounds from the starting materials in thebox without using LDA . O O O O H H H 3 C CH 3 H 3 C OCH 3 a) b) c) O O O O O CH 2 CH 3 H 3 C OCH 3 CH 3 H 3 C d) e) f) O OH O CH 3 H 3 C CH 3 CH 3 5. The following aromatization can take place under basic or acidic conditions. Using what you know about dehydration reactions, provide a detailed mechanism
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Unformatted text preview: for each transformation. a) O OH OH-, HO H 3 O + , HO b) O OH 6. Enamines and iminium ions exhibit reactivity similar to enols and carbonyls. Keeping this in mind, please provide detailed mechanisms for the following transformations. CH 3 a) O H 3 C CH 2 N N H 3 C O CH 3 CH 3 b) NH 2 O O O Me cat. H + Me MeO MeO O NH 2 7. Please provide a detailed mechanism for the following transformation. O CO 2 Me CO 2 Me NaOMe H 3 O + CO 2 Me (2 equiv) CO 2 Me O 8. Please provide a detailed mechanism for each of following transformations. Briefly explain why different products are observed under the different reaction conditions. O 1 equiv. OH-a) O O O H 2 O CH 3 CH 3 O CH 3 O O O O H 3 C -b) 1 equiv. OMe MeOH 9. Please provide a detailed mechanism for the following transformation. It looks tricky, but you know all of the steps! O CH 3 O NaOH, MeOH CH 3 O CH 3 H 3 C O CH 3...
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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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ps6 (1) - for each transformation. a) O OH OH-, HO H 3 O +...

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