Introduction
This article discusses the chemical compound 2,4-dinitrophenylhydrazine (DNP), including its properties, uses, and impacts. Students who are taking a chemistry course may find this information useful for completing assignments.
Physical Properties:
DNP is a yellow crystalline solid that is stable under standard temperature and pressure (STP). It has a molecular weight of 221.12 g/mol and a chemical formula of C 6H 4N 4O 5.
Chemical Information:
DNP is a derivative of hydrazine, which is the combination of two hydrogen atoms and two nitrogen atoms in a molecule that has been linked together with a triple bond. DNP contains two nitrogen atoms bonded with two hydrogen atoms in the molecule.
DNP has a strong odour, described as smelling like "musty hay" or "burnt sugar."
Uses:
DNP is used for testing enzymes, especially enzymes found in living tissues and cells. Researchers use DNP to see how these enzymes work and how they are affected by different chemicals.
Impacts:
DNP is a dangerous chemical that can be harmful to both humans and the environment. It is a skin and respiratory irritant and can cause burns, blisters, and other injuries. DNP is also toxic to aquatic life and can contaminate water supplies. Ingesting or coming into contact with DNP can cause serious health problems, including death. For these reasons, it is important to handle DNP carefully and take precautions when working with it.
What is 2,4-Dinitrophenylhydrazine?
The 2,4-Dinitrophenylhydrazine is a chemical compound, C6H3(NO2)2NHNH, which is also known as DNPH, Borche's reagent and Brady's reagent. The dinitrophenylhydrazine is a red to orange coloured solid. The total compound is substituted hydrazine and is often used qualitatively to test for the carbonyl groups that are associated with ketones and aldehydes. Also, these hydrazone derivatives can be used as evidence toward the original compound's identity. This derivative's melting point is often used, concerning a database of values, in determining the identity of a particular carbonyl compound. Relatively, it is sensitive to friction and shock; it is also a shock explosive. So, proper care must be taken towards its use and is usually supplied in the wet form to reduce its explosive hazard.
What is a 2,4-Dinitrophenylhydrazine or a 2,4 DNP Test?
The Brady's reagent (the 2,4-dinitrophenylhydrazine) is a red to orange coloured solid, which is usually supplied wet to reduce the explosion risk.
The structure of 2,4-Dinitrophenylhydrazine can be given as follows.
The derivatives of 2,4-DNP offer a convenient way of separating a mixture of ketones and aldehydes components. Instead of attempting to perform this by the fractional distillation directly, a chemist firstly may take advantage of the easy separation of 2,4-DNP derivatives by column chromatography. Since their formation from ketones and aldehydes is reversible, the separated derivative hydrolysis will regenerate the original carbonyl compounds.
Synthesis of 2,4-Dinitrophenylhydrazine
Although it is not hydrazine that is familiarly substituted, we can make a reasonable inference as hydrazine H2N-NH2 is a good nucleophile. Therefore, the 2,4-Dinitrophenylhydrazine synthesis is done from the product, and it is formed by reacting hydrazine with 2,4-dinitrochlorobenzene. The electron-accepting effect of two nitro groups makes this chloride displace easily.
Since the chlorine is ortho, deactivating, and para directing, we should nitrate chlorobenzene. Chlorobenzene is prepared readily from the benzene itself, and so the synthesis is complete, and the reaction can be given below.
Brady's Reagent
A Brady's reagent can be described as an aqueous solution of 2,4-dinitrophenyl hydrazine (DNP). It reacts with carbonyl compounds (aldehydes & ketone) to produce a coloured precipitate. These resultant precipitates have a sharp melting point. The melting points of these precipitates confirm the carbonyl compounds.
Also, benzoic acid is used as an antiseptic in medicines, in case of any urinary disorders, and in vapour form for bronchial tubes disinfection.
Acetic anhydride reacts with N2O5 to form acetyl nitrate.
(CH3CO)2O + N2O5 → 2CH3COONO2 (Acetyl nitrate)
The acid chloride reaction with water decreases with the increase of C-atoms in the alkyl groups.
CH3COCl > CH3-CH2-COCl > CH3-CH2-CH2COCl > …..
Identification of a Carbonyl Compound
The carbonyl compound is mixed with Brady's reagent acid solution in the methanol compound. These derivatives will result in coloured crystalline solids, known as 2,4-dinitrophenylhydrazones. These resultant crystals are filtered off and purified by the process of recrystallisation.
The melting temperatures of these derivatives are measured. Then, the original carbonyl compound is identified by comparing it to the tables of melting points of the 2,4-dinitrophenylhydrazine derivatives.
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Brady's reagent can also be used as a test for the presence of a carbonyl compound due to the appearance of the orange crystals when it is added to either an aldehyde or a ketone.
2,4 DNP Laboratory Test
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First, add 5ml of the 2,4-dinitrophenylhydrazine reagent in a test tube
Then, add 10 drops of an unknown compound and sharply tap the test tube with a stick or finger to mix. If the crystals do not form immediately, heat in a water bath (60oC) gently for 5 minutes
Now, cool the compound in an ice bath until the crystals form. Then, collect the crystals by vacuum filtration with a Hirsch funnel
After that, allow the crystals to dry on the Hirsch funnel by drawing the air through the crystals. Make a note of the melting point on the Report sheet
Usually, the crystals are pure enough to produce a good melting point. Although, recrystallise from a minimum volume of ethanol if the melting point range is too large.
Reaction with Ethanal
Let us look at the 24 DNP test for aldehydes and ketones or the 24 DNP test for ketones. The alkene ozonolysis gives 24 DNP test positive
The 2,4-Dinitrophenylhydrazine reacts with aldehydes and ketones to further form a 2,4-dinitrophenylhydrazone. For example, with Ethanal, it can be given as;
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The reaction is a condensation reaction (with the elimination of water). The restaurant product is named with the name of either aldehyde or ketone, followed by a 2,4-dinitrophenylhydrazone. For suppose, Ethanal 2,4-dinitrophenylhydrazone.
The 2,4-dinitrophenylhydrazine can be used as a process for the identification of aldehydes and ketones. The formed 2,4-dinitrophenylhydrazone is a solid that is purified, and the melting point is determined. The comparison of a melting point with a table of known values could identify the compound as aldehyde or ketone
All the 2,4-dinitrophenylhydrazone derivatives are orange or yellow solids
Often, the solution of 2,4-dinitrophenylhydrazine is called Brady's reagent.
Conclusion:
DNP is a dangerous chemical that can be harmful to both humans and the environment. It is a skin and respiratory irritant and can cause burns, blisters, and other injuries. DNP is also toxic to aquatic life and can contaminate water supplies. Ingesting or coming into contact with DNP can cause serious health problems, including death. For these reasons, it is important to handle DNP carefully and take precautions when working with it.
FAQs on 2,4-Dinitrophenylhydrazine
1. What is the product of an aldehyde with hydrazine?
The product of an aldehyde with hydrazine is a 2,4-dinitrophenylhydrazone. This is a solid that is purified, and the melting point is determined. The comparison of a melting point with a table of known values could identify the compound as either an aldehyde or ketone. One can find the melting point in an organic chemistry table. The two most common uses of the 2,4-dinitrophenylhydrazone derivatives are as a process for the identification of aldehydes and ketones and for the activity of hydrazine. Students are encouraged to try the 24 DNP test for aldehydes and ketones or the 24 DNP test for ketones. Vedantu teachers are available for helping and guiding the students.
2. How precipitation occurs in 24 DNP tests?
The 2,4-dinitrophenylhydrazone is the product of an aldehyde or ketone with hydrazine. If you notice, there are two moles of water for every mole of hydrazine. This makes it possible to identify this compound as either an aldehyde or ketone using recrystallisation. In the reaction, two moles of water are eliminated, and this is what results in precipitation. Withdrawing a small sample and allowing it to dry will give you a good representation of the melting point range for that particular aldehyde or ketone. It is a good idea to recrystallise the compound before you determine the melting point. This makes it easier to get a good representation of the melting point range. The sample usually does not have to be pure enough for one's particular experiment, so do not spend too much time purifying your sample.
3. Does Ethyl 4-Hydroxybenzoate and phenol react?
A mixture of 4-hydroxybenzoic acid methyl ester and Phenol react in the presence of dry methanol to give the methyl 3-[(4-hydroxyphenyl)azo]propanoate. This is a yellow precipitate that forms when these two compounds are mixed together in the right ratio. It can be purified by recrystallisation. The melting point of the methyl 3-[(4-hydroxyphenyl)azo]propanoate is 122-123 degrees Celsius. In order to do the 24 DNP test for aldehydes and ketones, it is necessary to know the reaction between an aldehyde or ketone and hydrazine. Allowing Ethanal to react with 2,4-dinitrophenylhydrazine in the presence of dry methanol gives methyl 3-[(4-hydroxyphenyl)azo]propanoate as a yellow precipitate that is easily purified by recrystallization. The melting point of this product is 122-123 degrees Celsius. This makes it possible to identify the product as either an aldehyde or ketone using recrystallisation. The reaction between an aldehyde or ketone and hydrazine can also be used to test for the presence of these compounds.
4. What are the problems of using 2,4-Dinitrophenylhydrazine for the Identification of carbonyl compounds?
2,4-Dinitrophenylhydrazine is the only reagent that can be used for the identification of carbonyl compounds. However, it is not without its problems. It is very sensitive to changes in pH and needs to be handled with special caregiving attention to disposal. Since 2, 4-dinitrophenyl-hydrazine (2,4-DNP) forms highly explosive azides. Only small quantities should be used at once. This makes it difficult to store and use. Furthermore, it is easy for hydrazine to come in contact with the reagent because of its gaseous state. The use of dry methanol also helps to minimise the amount of hydrazine that is lost. It is important to understand the reaction between an aldehyde or ketone and hydrazine in order to use 2,4-DNP for the identification of carbonyl compounds. The reactions are fairly simple and can be performed easily with standard laboratory equipment. With a little practice, you will be able to identify carbonyl compounds using 2,4-DNP.
5. How does the 2,4-Dinitrophenylhydrazine and ethanal react?
The reaction between Ethanal and 2,4-dinitrophenylhydrazine in the presence of dry methanol gives methyl 3-[(4-hydroxyphenyl)azo]propanoate as a yellow precipitate that is easily purified by recrystallisation. The melting point of this product is 122-123 degrees Celsius. This makes it possible to identify the product as either an aldehyde or ketone using recrystallisation. The reaction between an aldehyde or ketone and hydrazine can also be used to test for the presence of these compounds. Students often have difficulty understanding the reaction between an aldehyde or ketone and hydrazine. They can refer to Vedantu for more information about how these reactions work.
6. How can we notice the difference between aldehydes and ketones?
The difference between the aldehyde and ketone is the presence in the aldehyde of a hydrogen atom bound to the double bond of carbon-oxygen. In fact, ketones are not hydrogen. The hydrogen atom presence makes it very simple to oxidize aldehydes. They are also fast reduction agents.
7. If there is a positive 2/4 DNP test, what does it specify?
The 2,4-Dinitrophenylhydrazine is used for the qualitative identification of aldehyde or ketone functional group carbonyl functionality. The alkene ozonolysis gives 24 DNP test positive, if a positive test is given by the formation of a precipitate, known as a dinitrophenylhydrazone, orange, red, or yellow.
8. Why does glucose not offer a 2/4 DNP test?
This is due to glucose not reacting with the 2,4DNP reagent and Schiff's reagent despite having an aldehydrated group. It produces either α-anomer after the internal cycling. There is no free aldehyde group that is present in these forms. Therefore, it does not produce any aldehyde group reaction.
9. Does alcohol react With Brady's Reagent?
Ketones and aldehydes react to the precipitates of orange, reddish-orange, or yellow with the 2,4-dinitrophenylhydrazine reagent, whereas alcohols do not react. This is one of the successful techniques for checking for the drug existence or demonstrating its absence.