CHEM 263 - Exam I - June 2, 2006

CHEM 263 - Exam I - June 2, 2006 - cantharidin the active...

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Chemistry Department University of Alberta CHEM 263 Exam I Friday, June 2, 2006 1. The IR and 1 H NMR spectra of a compound of molecular formula C 10 H 12 O are given below. Propose a structure for this compound. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (31-05-06)
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a. Calculate the degree of unsaturation. b. List the possible functional groups gleaned from the molecular formula. c. What functional group(s) is/are present? Omit the benzene ring. d. Propose a structure for this compound. 2. Sketch the expected 1 H NMR spectrum of the following compound: 3. Predict the products of the reaction of hydrogen chloride with 2-methyl-1,3- butadiene under the following conditions and propose a mechanism for their formation: a. Kinetic control b. Thermodynamic control 4. Propose a Diels-Alder synthesis of the powerful vesicant (blister inducer) cantharidin, the active ingredient of the aphrodisiac “Spanish Fly”.
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Unformatted text preview: cantharidin, the active ingredient of the aphrodisiac “Spanish Fly”. You may assume that starting materials containing no more than six carbon atoms are available, along with any inorganic materials you may need. 5. Explain why azirines of structure 1 have never been isolated, whereas the isomeric azirines of structure 2 are well known. 6. Draw the structure of 2-nitroaniline. 7. Name the following compound: 8. Propose a mechanism to account for the following reaction: 9. Provide a synthetic pathway for the following transformation: 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 2, 2006...
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