assignment8 - a) OH OH b) OH OH H H C 6 H 10 O C 7 H 10 O...

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CHM 3120 Assignment 8 1. The following compound was prepared recently by a graduate student as part of her thesis work. After several days at room temperature, the student found that the structure of the product had changed. How do you account for her observation? CH 3 CH 3 2. When the following molecule is heated, a mixture of three products is obtained. Provide a mechanism that accounts for the production of these products. H 3 C H 3 C CH 3 CH 3 + CH 3 CH 3 + CH 3 CH 3 3. When 1, 3, 5-cyclooctatriene that has been labeled with deuterium at the 7 and 8 positions is heated, a mixture of products is obtained in which deuterium is found only at the 3, 4, 7 and 8 positions. How can you account for the selectivity of this process? 4. Predict the products formed by acid-catalyzed dehydration of the following:
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Unformatted text preview: a) OH OH b) OH OH H H C 6 H 10 O C 7 H 10 O c) H C 10 H 16 O OH OH 5. Give a mechanism to account for the following transformation: OAc H 2 SO 4 HOAc 6. Explain why optically active exo-bicyclo [2.2.1] heptanol-2 (norborneol) is racemized when treated with acid. Hint: Consider the fact that in these rearrangements, those bonds that are antiperiplanar to leaving groups are the ones that migrate. H OH OH 7. Explain why optically active endo-bicyclo [2.2.1] heptanol-2 (norborneol) is racemized when treated with acid H OH OH 8. Explain why the dehydration of borneol with aqueous acid gives camphene OH H 2 SO 4 9. Explain the following observation: N Cl MeOH N OMe 10. Give a mechanism to account for the following observation: O O H O O...
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This note was uploaded on 12/11/2009 for the course CHM Chm3120 taught by Professor Olgilvie during the Spring '09 term at University of Ottawa.

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assignment8 - a) OH OH b) OH OH H H C 6 H 10 O C 7 H 10 O...

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