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4-Nitroacetanilide is another name for para nitro acetanilide. A chemical product that is a derivative of nitro acetanilide formed from a combination of nitrating and acetanilide is classified as para nitro acetanilide. A trace of ortho product is created along with the para product.
p-Acetamido Nitrobenzene, N-(4-nitrophenyl) acetamide, N-Acetyl-4-nitroaniline, and p-Nitroacetanilide are some of the other names for p-Nitroacetanilide.
Nitration is used to create the chemical molecule p-nitroacetanilide from acetanilide. P-nitroacetanilide is generated when acetanilide is treated with a nitrating combination consisting of nitric acid and sulfuric acid. In addition to p-nitroacetanilide, o-nitroacetanilide is generated as a minor product. Because o-nitroacetanilide is very soluble in alcohol, crystallization is a simple method for isolating p-nitroacetanilide.
Principle:
Acetanilide nitration can be used to make p-Nitroacetanilide. Acetanilide’s acetamido group (-NHCOCH3) is para and directed. Thus, nitration results in the formation of an o- and p-nitro acetanilide mixture:
Because the acetamido group is bulky, it will produce steric obstruction at the ortho position. As a result, p-nitro acetanilide can be generated as a significant product. Furthermore, when crystallized from ethyl alcohol, the p-nitro acetanilide crystallizes mostly as colourless crystals, whilst the ortho isomer stays in solution.
Preparation of p-Nitroacetanilide:
- An electrophilic substitution reaction is one of the chemical processes involved in this process.
- Because the -NHCOCH3 is an electron releasing group, the electrophile -NO2 will connect to the para position.
- Because aniline nitration is not feasible, the amino group is oxidized with the nitrating mixture to produce nitro anilines.
- To protect the amino group from oxidation, acetanilide is first nitrated to produce p-nitroacetanilide, which is then hydrolyzed to produce p-nitroaniline, which is difficult to acquire from direct nitration.
p-Nitroacetanilide applications:
- It is used in the pharmaceutical industry to make paracetamol and phenacetin.
- Used in insecticides and rubber chemicals
- Also used as a dye intermediate.
- UV spectroscopic measurements were utilized to determine the hydrolysis of 4-Nitroacetanilide as a test substrate.
- It was also employed in the synthesis of 4-amino acetanilide.
FAQs
In the crude sample, how is p-nitroacetanilide separated from o-nitroacetanilide?
Because o-nitroacetanilide is more soluble in ethanol, it stays in the mother liquor and only p-nitroacetanilide separates during crystallization.
What is the chemical formula of p-nitroacetanilide? Also, include its IUPAC name.
C8H8N2O3 is the formula for p-nitroacetanilide, and the IUPAC name is N-(4-nitrophenyl)acetamide.
What exactly is a nitrating mixture?
The nitrating mixture is a mixture of concentrated sulphuric acid and fuming nitric acid.
Why is the ortho derivative minor but the para product is significant? Give an explanation.
This is an electrophilic substitution process, and the generated nitronium ion is oriented towards the ortho and para positions. The nitronium electrophile is driven more towards the para position due to the steric barrier in the ortho position. As a result, the para product is significant.
