Does 2,4-dinitrophenylhydrazine react with aromatic aldehydes, e.g. benzaldehyde (phenylmethanal), in a condensation reaction similar to 2,4-DNPH's reaction with aldehydes and ketones ?
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$\begingroup$ Yes, it does react $\endgroup$– WaylanderCommented Jun 20, 2018 at 12:45
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$\begingroup$ @Waylander Just to complete your comment: Yielding a solid of m.p.=237C. It is used as derivative in the classical identification of organic compounds. $\endgroup$– Raoul KesselsCommented Jun 20, 2018 at 13:15
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$\begingroup$ @Raoul-Kessels Thank you. I no longer have database access so cannot go looking for such data. Perhaps you should turn your comment into an answer $\endgroup$– WaylanderCommented Jun 20, 2018 at 14:21
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$\begingroup$ @Waylander I had my old book on my desk ;-) $\endgroup$– Raoul KesselsCommented Jun 20, 2018 at 14:23
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1 Answer
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2,4-DNPH is a derivatization reagent for the identification of ketones and aldehydes. This was extensively used in organic analysis before instrumental methods were readily available. You determined the boiling point of the problem, which in the case of benzaldehyde is $179\ ^{\circ}\mathrm{C}$ , then you made a solid derivative and determined it's melting point. In the case of benzaldehyde and 2,4-DNPH that would be $237\ ^{\circ}\mathrm{C}$ . Then you go to the tables, cross check both values and had benzaldehyde identified.
For aldehydes and ketones there are different options: oxime, semicarbazone, phenylhydrazone, p-nitrophenylhydrazone and 2,4-dinitrophenylhydrazone. The latter one was usualy preferred because they have higher melting points and so it was easier to get a solid even if not totally pure.
