2,4-Dinitrophenylhydrazine test

2,4-Dinitrophenylhydrazine (brady’s Reagent)

• Has a chemical compound c6 h3 (no2)2 nhnh2.

• The compound contains a benzene ring, two nitro groups, and a hydrazine (two
nitrogen atoms bonded directly to each other) functional group.

• Dinitrophenylhydrazine is an orange solid, it is a substitute to hydrazine, and is

often used to qualitatively test for carbonyl groups associated with aldehydes and
ketones.

The 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 -NH2 group to the C=O carbonyl group, followed by the elimination of a H2O molecule:

• Crystals of different hydrazones have characteristic melting and boiling points,

allowing the identity of a substance to be determined in a method known
as Derivatization. In particular, the use of 2,4-dinitrophenylhydrazine was
developed by Brady and Elsmie.

• Modern spectroscopic and spectrometric techniques have superseded these

techniques.

• Dinitrophenylhydrazine 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.
Positive result:

• The formation of yellow-orange or orange- red precipitate. (known as

a dinitrophenylhydrazone). If the carbonyl compound is aromatic, then the
precipitate will be red; if aliphatic, then the precipitate will have a more yellow color

Sodium Bisulfite test

• a test for aldehydes in which aldehydes form a crystalline salt upon addition of 40%
aqueous solution on sodium bisulfite

• Sodium bisulfite is sued to prevent browning ( caused by oxidation ) and to kill

microbes.

• In wine making, sodium bisulfite releases sulfur dioxide gas when added to water or
products containing water.

• Additional information:

• Sodium bisulfite generally recognized as safe in the extremely tiny quantities

required to use it as a preservative.

• At very high does in its concentrated form, sodium bisulfite any quantity of sodium
bisulfite greater than 10 parts-per-million (ppm) has to be listed in the ingredients
list.

Result and discussion:

• Acetaldehyde- formed less crystal precipitate

• Acetone – formed more crystal precipitate

*carbonyl group in acetone molecule is highly

Polar and can undergo nucleophilic addition reaction with nucleophiles (nAhso3)