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2008_Exam_2_Answer_Key

2008_Exam_2_Answer_Key - Organic Chemistry c3046y 2nd Hour...

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2nd Hour Exam Organic Chemistry c3046y Monday, Mar. 10, 2008 Prof. Leighton Answer Key
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Name: Page 1 1. (20 pts) Predict the product AND provide a detailed mechanism for its formation. O O MeO 1. NaOMe, MeOH 2. H 3 O + (mild, just a quench) O OMe O MeO O MeO OMe O O MeO OMe O H OMe O MeO OMe O H H MeO O MeO OMe O OMe O O MeO O OMe O H MeO O OMe O H 3 O + H +
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Page 2 Name: 2. Predict the major product, if any, of the following reactions: a. (10 pts) b. (10 pts) O H O Me 2 NH + H + Me O Me O O + OH, H 2 O Me O O O NMe 2 O H N Me Me OH H N Me Me Me O O Me O Robinson Annulation Mannich Reaction
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Name: Page 3 3. (20 pts) Mechanistically, the following reaction can be thought of as a modified Robinson Annulation. Provide a detailed mechanism to account for this amazing reaction: OH H 2 O O H O O HO H O H O O H O H O H O H O H OH O H O O O H O H
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Name: Page 4 4. a. (10 pts) Provide a mechanism for this unusual decarboxylation reaction. b. (10 pts) Predict the product of the following aldol reaction, paying particular attention to stereochemistry.
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