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Mechanism & Reducing Agent

When amide X is treated with lithium aluminum hydride, the corresponding amine can be isolated in good yield. (a) Provide a concise mechanism for this reaction. (b) Draw the structure of a reducing agent capable of converting an ester to the corresponding aldehyde. Give an explanation as to how this reagent works.

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Hi,

I have attached a mechansim for the reduction of the amide. The net effect of amide reduction is to convert the amide carbonyl group into a methylene group (C=O goes to CH2). This kind of reaction is specific for amides and does not occur with other carboxylic acid derivatives.

The mechansim of the reaction begins ...

Solution Summary

I have attached a mechansim for the reduction of the amide. The net effect of amide reduction is to convert the amide carbonyl group into a methylene group (C=O goes to CH2). This kind of reaction is specific for amides and does not occur with other carboxylic acid derivatives. The mechansim of the reaction begins with hydride addition, which gives a tetrahedral intermediate. Elimination of an aluminium alkoxide leads to an iminium ion. The addition of a second hydride gives the final product (see attached).

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