Lecture39 - Reduction of Aldehydes and Ketones Metal...

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12/1/09 1 Oxidation of Aldehydes and Ketones Oxidation of Aldehydes • Oxidizing agents commonly used to oxidize aldehydes to carboxylic acids are potassium permanganate and chromic acid Oxidation of Aldehydes and Ketones Tollens Reagent • Aldehydes are also oxidized to carboxylic acids by silver(I) dissolved in aqueous ammonia:
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12/1/09 2 Oxidation of Aldehydes and Ketones Tollens Reagent • Aldehydes are also oxidized to carboxylic acids by silver(I) dissolved in aqueous ammonia: Precipitates as a silver mirror Oxidation of Aldehydes and Ketones Oxidation of Ketones • Ketones are not normally oxidized by either potassium permanganate or chromic acid.
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12/1/09 3 Reduction of Aldehydes and Ketones Metal Hydride Reductions • By far the most common laboratory reagents for reducing aldehydes and ketones to alcohols are sodium borohydride , lithium aluminum hydride , and their derivatives.
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Unformatted text preview: Reduction of Aldehydes and Ketones Metal Hydride Reductions • It is convenient to think of these reagents as nucleophilic hydride ( H:-) 12/1/09 4 Reduction of Aldehydes and Ketones Metal Hydride Reductions • It is convenient to think of these reagents as nucleophilic hydride ( H:-) Reduction of Aldehydes and Ketones Metal Hydride Reductions • It is convenient to think of these reagents as nucleophilic hydride ( H:-) Aqueous acid is added afterward to protonate the alkoxide ion. 12/1/09 5 Reduction of Aldehydes and Ketones Metal Hydride Reductions • Lithium aluminum hydride is a very powerful reducing agent and will also reduce carboxylic acids and esters. Reduction of Aldehydes and Ketones Metal Hydride Reductions • Sodium borohydride is much less reactive (and therefore more selective)—it will reduce only ketones and aldehydes rapidly....
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This note was uploaded on 07/02/2011 for the course CHEM R340 taught by Professor Tolbert during the Summer '11 term at Indiana.

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Lecture39 - Reduction of Aldehydes and Ketones Metal...

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