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Problem_Set_9_solution

Problem_Set_9_solution - Chem 358 Spring 2007 Problem Set...

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Chem 358 Spring 2007 Problem Set 9 -Answers 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 Omit the following: 40, 49, 68(c), 69, 71(a), (b), 73(a)-(e), (g), (i), (l), 74, 78(e), 79(a), (d)-(i) Additional Problems Note that some of the solutions use reactions we did not get to. The problem set was put together before I decided on what to exclude from the next exam. So you are only responsible for what we have covered. 1. (a) The first step is Claisen condensation while the last step is an intramolecular adol condensation. In addition, the solution uses some of the reactions we did not get to. One is the Michael addition (second step). In this case, the Michael adduct can be hydrolyzed in acid since it is an ester to give the β -keto acid, which we have found earlier to decarboxylate readily when heated. CH 3 OC 2 H 5 O 2 1. NaOEt O O O Claisen Na + CH 3 O CH 3 O O O O H 3 O + CH 3 O O O O H 3 O + ! Decarboxylation CH 3 O O NaOH, H 2 O, ! Aldol Condensation O CH 3 Michael Addition O CH 3 O O O H Hydrolysis (b) The first step is an intramolecular Claisen. The second step is alkylation using the allyl bromide. The
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