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Unformatted text preview: and all charges (if applicable). O H NH 3 + H + H 2 O HN H H 3 N H O-H 2 N H OH H + H 2 N H OH H H 2 N 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). HOH + H 2 O = -OH + H 3 O + K = 10 -15.7 eqn1 CH 3 C(=O )CH 3 + H 2 O = CH 3 C(=O )CH 2-+ H 3 O + K = 10 -20 eqn 2 Add eqn 2 + reverse of eqn1: -OH + CH 3 C(=O )CH 3 = CH 3 C(=O )CH 2-+ H 2 O K= 10 +15.7 x 10-20 = 10- 4.3 Unfavourable equilibrium constant. . reaction will not proceed to completion 5 (4) Synthesis. Show how aldol reactions can be used to synthesize the following α , β-unsaturated carbonyl-containing compounds. Show the intermediate aldol formed in each case. See next page O O O OH HO O O OH via Aldol intermediate O OH O O...
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- Summer '10
- Mole, Carbonyl, Cl Cl, Keto-enol tautomerism, HO O