Problem_Set_8

Problem_Set_8 - O O from O O N H 6 Suggest a plausible...

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Chem 3580 - Spring 2009 Problem Set 8 Chapter 18: 55, 57, 58, 60, 62, 65, 67-70, 73, 74, 76, 78, 81, 83 Additional Problems . 1. Design a multistep synthesis of each of the following molecules making use of the indicated compounds as the source of all the carbon atoms in your final product. You may use any inorganic or other organic reagents so long as they don’t supply any carbon to the final product. O CH 3 H 3 C O CH 3 O CH 3 O from and (a) O H 3 C O O CH 3 O O from Br and (b) 2. Use acetoacetic ester synthesis to prepare the following. O O O O (a) (b) (c) 3. Use malonic ester synthesis to prepare the following. COOH COOH from COOH (a) (b) 4. Prepare the compound shown using Michael reaction. O O 5. Prepare the same compound in (4) using enamine chemistry
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Unformatted text preview: O O from O O N H 6. Suggest a plausible mechanism to account for each of the following transformations. Ph O O 1. CH 3 CH 2 O — 2. O (a) O Ph O CO 2 CH 2 CH 3 O Na +-OCH 2 CH 3 , CH 3 CH 2 OH O CO 2 CH 2 CH 3 (b) O 7. Fill in the missing reagents in the reaction sequence shown below. More than one synthetic step may be needed for each transformation. Br Br HO 2 C CO 2 H (b) CH 3 O 2 C CO 2 CH 3 (a) (c) O CO 2 CH 3 O CO 2 CH 3 O CO 2 CH 3 O (d) (e) 8. What reagents ((a)—(e) would be required to carry out the following transformations? H O O O Na + — O O CH 3 CH 2 O O (a) (b) (c) (d) (e)...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell.

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Problem_Set_8 - O O from O O N H 6 Suggest a plausible...

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