week 4 - 3 - Week 4 July 14, 2010 Nucleophilic Addition to...

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Week 4 July 14, 2010 Nucleophilic Addition to Aldehydes and Ketones: Acidic Conditions Provide a complete curved-arrow mechanism for each of the following reactions: O H 2 O H + OH OH a vicinal diol O H H 2 O H + H HO OH a geminal diol or hydrate Why is the hydration of an aldehyde reversible? Reading : Section 19.7 26
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July 14, 2010 Equilibria for Hydration of Carbonyls: Relative Reactivity of Carbonyl Compounds Explain the observed ranking of equilibrium constants for carbonyl hydration in the following substrates: R R' O R R' HO OH F 3 C CF 3 O F 3 C H O H H O H 3 C H O H 3 C CH 3 O CH 3 O K = [hydrate] [carbonyl] Carbonyl Compound 1 x 10 6 3 x 10 4 2 x 10 3 1 1 x 10 –3 9 x 10 –6 H 2 O K The following compound has 2 carbonyl groups. Which one will become hydrated under aqueous conditons? Explain why the hydration equilibrium ratio K is equal to 0.8, that is, significantly larger than the ratio for most unsubstituted ketones such as acetone (above). H
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week 4 - 3 - Week 4 July 14, 2010 Nucleophilic Addition to...

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