text: DNPH is a reagent in instructional laboratories on qualitative organic analysis. Bradys reagent or Borches reagent, is prepared by dissolving DNPH in a solution containing methanol and some concentrated sulfuric acid. This  solution is used to detect ketones and aldehydes. A positive test is signalled by the formation of a yellow, orange or red precipitate of the dinitrophenylhydrazone. Aromatic carbonyls give red precipitates whereas aliphatic carbonyls give more yellow color. The reaction between DNPH and a generic ketone to form a hydrazone is shown below:
  :RRC=O   +   CH(NO)NHNH   →   CH(NO)NHN=CRR   +   HO
  This reaction is, overall, a condensation reaction as two molecules joining together with loss of water. Mechanistically, it is an example of addition-elimination reaction: nucleophilic addition of the -NH group to the C=O carbonyl group, followed by the elimination of a HO molecule:
  DNP-derived hydrazones have characteristic melting points, facilitating identification of the carbonyl. In particular, the use of DNPH was developed by Brady and Elsmie. Modern spectroscopic and spectrometric techniques have superseded these techniques.
  DNPH does not react with other carbonyl-containing functional groups such as carboxylic acids, amides, and esters, for which there is resonance-associated stability as a lone-pair of electrons interacts with the p orbital of the carbonyl carbon resulting in increased delocalization in the molecule. This stability would be lost by addition of a reagent to the carbonyl group. Hence, these compounds are more resistant to addition reactions. Also, with carboxylic acids, there is the effect of the compound acting as a base, leaving the resulting carboxylate negatively charged and hence no longer vulnerable to nucleophilic attack.