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Can I distinguish between an aldehyde and a carboxylic acid using Tollen's reagent? If not, how else can I distinguish between them (without using 2,4-DNPH)?

Corrie writes ...
 
In principle you could because the aldehyde should give a silver mirror whereas the carboxylic acid should not - provided it is not methanoic acid, which contains the aldehyde functional group as well the carboxylic acid functional group. Methanoic acid reacts very slowly with Tollen's reagent.
 
Carboxylic acids should give off carbon dioxide when a solution is added to little sodium hydrogencarbonate (or carbonate) solid or solution. Aldehydes should not react in this way, unless they contain a little acid impurity as a result of oxidation.

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updated: 14 November 2007

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