Problem_Set_9 - and (a) O H 3 C O O CH 3 O O from Br and...

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Chem 358 Spring 2007 Problem Set 9 Chapter 22: 22 .20(c), 27, 40, 48-50, 52, 54, 56, 59, 61, 63, 65, 67, 68-71, 73, 74, 78 (a), (c), (e), 79 Additional Problems 1. Using methods described in Chapter 22, 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
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Unformatted text preview: and (a) O H 3 C O O CH 3 O O from Br and (b) 2. Suggest a plausible mechanism to account for each of the following transformations. O O O O O O 1. CH 3 CH 2 O 2. O (a) 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 3. 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 O (d) (e)...
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