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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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- Spring '09
- Organic chemistry, Chemical compound, graduate student