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Unformatted text preview: Chemistry 35: Organic Monofunctional Compounds Section 9: December 1, 2008 Prof. Huestis, Fall 2008 TA: Leila Yeh Beach CONJUGATED SYSTEMS 1] Nucleophile Addition [A] 1,2-Addition Overall Reaction Mechanism Notes 1,2-addition gives the kinetic product (the product which is fastest to form). 1,2-addition is favored by strong nucleophiles. [B] 1,4-Addition Overall Reaction Mechanism O O O Nuc 1,4 - addition 1,2 - addition Nuc O H + OH Nuc ,-unsaturated carbonyl Nuc O O Nuc H + OH Nuc ,-unsaturated carbonyl O Nuc ,-unsaturated carbonyl H + O Nuc O Nuc O Nuc H + OH Nuc B H-B O Nuc ,-unsaturated carbonyl Notes 1,4-addition gives the thermodynamic product (the lowest energyor most stable product). 1,4-addition is favored by weak nucleophiles. For intermediate nucleophiles (NaBH 4 and grignard reagents), consider sterics when decisind whether 1,2-addition or 1,4-addition is favored....
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