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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Lecture39 - Reduction of Aldehydes and Ketones Metal...

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