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CHEM 263 - Exam IIa - June 12, 2006

CHEM 263 - Exam IIa - June 12, 2006 - a Give the structure...

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Chemistry Department University of Alberta CHEM 263 Exam II Monday, June 12, 2006 1. Name the following compounds: a. (S)-4-ethoxy-5-hydroxy-4-methyl-3-hexanone b. trans -3-chlorocyclohexanecarbaldehyde 2. Complete the following partial structure of (E,3R)-3-methyl-4-hexenal: 3. What reagents would you use to effect the following conversions?
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a. b. c. d. e. 4. Give the structure(s) of the principle organic products of the following reactions: a. b. c.
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d. e. 5. Provide a synthetic pathway for the following transformation: 6. Circle the weakest acid.
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7. Propose mechanisms for the following reactions: a.
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b.
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8. The structure of the sex pheromone of the female tsetse fly has been confirmed by the following synthesis. Compound C appears to be identical to the natural pheromone in all respects (including the response of the male tsetse fly). a. Give the structure of compound “A”.
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b.
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Unformatted text preview: a. Give the structure of compound “A”. b. Give the structure of compound “B”. c. Give the structure of compound “C”. 9. When propanone is dissolved in 18 O-enriched water, the isotopic label becomes incorporated into the carbonyl group. Present a mechanistic explanation. 10. Complete the following synthesis of Ibuprofen, an anti-inflammatory drug, by giving the reagents and/or structures of the intermediates “A” to “J”. There are a number of ways to complete the step involving “H”, “I” and “J”. If you wish to use fewer, or more, feel free to do so. CHEM X6X Home Page | Faculté Saint-Jean | University of Alberta | Chemistry Department This page is maintained by Dr. Ed Blackburn ( [email protected] ), course instructor. Updated June 12, 2006...
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