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2007_Exam_2_Answer_Key

2007_Exam_2_Answer_Key - Organic Chemistry c3046y 2nd Hour...

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2nd Hour Exam Organic Chemistry c3046y Monday, Mar. 5, 2007 Prof. Leighton Answer Key
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Name: Page 1 1. Provide a detailed mechanism to account for the following transformations. a. (15 pts) b. (10 pts) Ph OH O O Δ Ph O H + CO 2 H + N Ar Me O N Me Ar + O Me H + N Me Ar Me O H H + N H 2 C Ar Me O H H N Ar Me O H N Ar Me O H Ph O O O H OH Ph + CO 2 Tautomerize
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Page 2 Name: 2. (20 pts) Show how a double Mannich reaction could be used to synthesize the illustrated target. You should clearly indicate the required starting materials, and show how the reactions proceed. You do not need to show a detailed mechanism, but you should show the key intermediates. N Me O H + Target Starting Materials O MeNH 2 H H O 2 MeNH 2 H H O + H + H H N Me H O H + OH O NH Me O N Me H H H + OH N Me H H N O Me H +
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Name: Page 3 b. (5 pts) Normally, one would expect the 6-membered ring starting material to be more stable than the 9- membered ring product. Explain (concisely!) why this reaction proceeds the way it does to give the presumably less stable 9-membered ring product.
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