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Unformatted text preview: HO HO O H+ O O NH 2 OH H + 1. NaH HO H + O HO + H 2 O diketo tautomer 2. CH 3 CH 2 I 4a (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement and all charges (if applicable). O H NH 3 + H + H 2 O HN H 4b (6) Use the appropriate pKa equations to show why - OH (pKa H 2 O 15.7) cannot be used to quantitatively deprotonate acetone CH 3 C(=O )CH 3 (pKa 20). 5 (4) Synthesis. Show how aldol reactions can be used to synthesize the following , -unsaturated carbonyl-containing compounds. Show the intermediate aldol formed in each case. O O...
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- Summer '10