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Leila Section Week 6a

Leila Section Week 6a - Chemistry 35 Organic Monofunctional...

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Chemistry 35: Organic Monofunctional Compounds Section 6: November 3, 2008 Prof. Huestis, Fall 2008 TA: Leila Yeh Beach Mistakes to Avoid / Important Things to Remember 1. Don’t forget acid work up steps following strong nucleophile (LiAlH 4 , NaBH 4 , Organolithiums, Grignard Reagents) reactions. 2. Remember, reactions of carboxylic acids, esters, and amides with hydride (LiAlH 4 ) and carbide (Organolithiums, Grignard Reagents) reducing agents always, always proceeds through two reductions. You will never, ever, ever stop at an aldehyde/ketone/imine intermediate. (The one exception to this rule is hydride reduction with DIBAL at -60 o C – this allows you to stop at the aldehyde.) 3. Oxidation and reduction reactions cannot be accomplished with the addition of acid or base. You must use the appropriate oxidizing/reducing agents to achieve the following transformations: 4. Functional Group Reactivity Order Reactivity (toward nucleophile addition) Increases to the Right
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