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Unformatted text preview: Chemistry 35: Organic Monofunctional Compounds Section 7: November 10, 2008 Prof. Huestis, Fall 2008 TA: Leila Yeh Beach Summary of Nitrile Reactions R C N NITRILE (1) LiAlH 4 (2) H 3 O + OR R H O R NH 2 ALDEHYDES *when reacted with excess nitrile AMINES *when reacted with excess hydride DIBAL-60 o C H 3 O + 5 o C R H O ALDEHYDES KCN S N 2 R Br ALKYL HALIDE H 2 O, H 2 SO 4 CARBOXYLIC ACIDS R OH O (1) R'-MgBr o r R'-Li (2) H 3 O + R R' O KETONES One useful application of nitrile chemistry is the generation of β-dicarboxylic acids: Alpha Carbon Reactions of Carboxylic Acid Derivatives Important: We can’t readily α-deprotonate carboxylic acids, so doing a lot of α-carbon chemistry directly on carboxylic acids is difficult. We can, however, definitely pull α- protons off esters with the appropriate base. So, one way around the limitations of carboxylic acids is to convert them to esters, do all the α-carbon chemistry you want, and then convert any ester functionality in the product back into a carboxylic acid. OH O Formic Acid P Br 2 OH O Br CN OH O CN H 2 SO 4 H 2 O HO OH O O β- dicarboxylic acid 1] The Claisen Condensation Overall Reaction Mechanism The Dieckmann Condensation is just an intramolecular Claisen Condensation: If you have the time and will, it might be worth the exercise to go through this...
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This note was uploaded on 02/13/2009 for the course CHEM 35 taught by Professor Dubois,j during the Fall '07 term at Stanford.
- Fall '07