2008_Exam_2 - Provide a detailed mechanism to account for...

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2nd Hour Exam Organic Chemistry c3046y Monday, Mar. 10, 2008 Prof. Leighton The exam is 5 pages long ( not including this one). Please make sure you have all of the pages. . . Question 1 (20 pts): Question 2 (20 pts): Question 3 (20 pts): Question 4 (20 pts): Name: ID#__________________________ Write your name on every page. . Question 5 (20 pts): Total (100 pts):____________ Signature:__________________________ Write complete but succinct answers. Good Luck!
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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)
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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
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Name: Page 3 3. (20 pts) Mechanistically, the following reaction can be thought of as a modified Robinson Annulation.
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Unformatted text preview: Provide a detailed mechanism to account for this amazing reaction: OH H 2 O O H O O HO Name: Page 4 4. a. (10 pts) Provide a mechanism for this unusual decarboxylation reaction. OH OH O OH Strong H + * * (Only product, label NOT scrambled.) b. (10 pts) Predict the product of the following aldol reaction, paying particular attention to stereochemistry. Me N O Me Me LDA Ph H O H 3 O + Name: Page 5 5. (20 pts) If compound A was treated with acid, it might reasonably be expected to rearrange to compound B . Propose a mechanism to account for this transformation. N O Me H + N O Me A B...
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This note was uploaded on 04/16/2008 for the course CHEM C3046 taught by Professor Leighton during the Spring '08 term at Columbia.

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2008_Exam_2 - Provide a detailed mechanism to account for...

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