To prevent collapse an acid must be used to protonate

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Unformatted text preview: structural examples with a mechanism for each. (4) 7. Cyclopentadiene (pKa ~15) and ethane (pKa ~60) both have sp3 hybridized carbons with hydrogens. Explain the large difference in pKa. (3) 8. When acetylide anion reacts with a carbonyl, a tetrahedral intermediate is formed. To prevent collapse, an acid must be used to protonate the resulting oxide. What acid would you choose and why? Which acid would you not want to use and why? (4) H O H3C C C- H R H3C C O- C ? R H H3C C OH C R 9. The pKa’s of the alpha- hydrogens in a ketone (20) and ester (25) are different. Why the difference? (4) 3 Part III: Reactions 10. Provide the major product for the following reactions. If the product i...
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