Para nitroacetanilide is also called 4-Nitroacetanilide, para nitroacetanilide is a chemical compound that is a nitroacetanilide derivative prepared from acetanilide and nitrating mixture. Along with para product a trace of ortho product is also formed.
To prepare p-Nitroacetanilide from acetanilide and acetic acid in the presence of nitrating mixture.
The organic compound p-nitroacetanilide is prepared from acetanilide through nitration. When acetanilide is treated with nitrating mixture that is a mixture of nitric acid and sulphuric acid p-nitroacetanilide is formed. Along with p-nitroacetanilide, o-nitroacetanilide is also formed as a minor product. Since o-nitroacetanilide is very much soluble in alcohol it is very easy to isolate p-nitroacetanilide through crystallization.
Also Read: Preparation of p-Nitroacetanilide Viva Questions |
The chemical reactions involved in this process is given below.
It is an electrophilic substitution reaction. The electrophile -NO2 will attach the para position because the -NHCOCH3 is an electron releasing group. Nitro anilines can be prepared by this type of reactions because nitration of aniline is not possible, amino group gets oxidized with nitrating mixture. In order to protect the amino group from oxidation acetanilide is first nitrated to give p-nitroacetanilide and then on hydrolysis to give p-nitroaniline which is difficult to obtain by direct nitration.
Other names – N-(4-nitrophenyl) acetamide, p-Acetamidonitrobenzene, p-Nitroacetanilide, N-Acetyl-4-nitroaniline
Colour of the crystals | Colourless |
Melting point | 214 o C |
Expected yield | 4gm |
The yield of p-Nitroacetanilide is _____gm.
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o-nitroacetanilide is more soluble in ethanol so that it remains in the mother liquor and during crystallization only p-nitroacetanilide separates out.
The combination of concentrated sulphuric acid and fuming nitric acid is called nitrating mixture.
The formula for p-nitroacetanilide is C8H8N2O3, and the IUPAC name is N-(4-nitrophenyl)acetamide.
This reaction is electrophilic substitution reaction and the nitronium ion formed is directed towards ortho and para positions. Due to steric hindrance in ortho position the nitronium electrophile is directed more towards para position. Therefore, para product is major.
It is used in pharmaceuticals in preparation of paracetamol and phenacetin. Used in pesticides and rubber chemicals also used as an intermediate for dyes.