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When aniline is treated with acetoacetate, the resulting substance is called nacetyl aniline. This, when subjected to H2SO4/HNO2/CH3COOH, will result in the production of paranito nacetyl aniline, which, when subjected to hydrolysis, will result in the production of para nito aniline.
How will the chemical processes that are required to convert aniline to p-nitroaniline be carried out?
H2SO4 is used to bring the nitro group into position at the para position. The para position, which has the maximum electron density, is chosen for the introduction of the nitro group since it is the most active place in the molecule. P-nitroaniline is produced through the hydrolysis of p-nitroacetanilide. Because of this, p-nitroaniline can be synthesized from aniline using this method.
The question that has to be answered is why it is not possible to make p-nitroaniline straight from aniline.
It is difficult to nitrate aniline due to the fact that aniline easily oxidizes into protonated aniline…. Keep up with BYJU’S to gain further insight into the other issues, such as nitration, that are being discussed.
What are the steps involved in converting aniline into p-nitroaniline?
In a round-bottom flask with a capacity of 100 mL, dissolve 4.0 mL of aniline in a volume of 10 mL of acetic acid. After adding 5 mL of acetic anhydride to this solution, thoroughly combine the ingredients by whirling the container. WARNING: the reaction is exothermic, and the temperature of the flask will rise.
Why does P-nitroacetanilide play such a significant role?
Explain yourself. This reaction can be classified as an electrophilic substitution reaction, and the nitronium ion that is generated is headed in the direction of the ortho and para positions. The nitronium electrophile is oriented more toward the para position because of steric hindrance in the ortho position. Thus, the byproduct plays a significant role.
Organic Chemistry: From Aniline to p-nitroaniline
34 questions found in related categories
Why does nitration of aniline not seem to be an option?
Because nitric acid oxidizes most of the aniline to yield tarry oxidation products along with just a minor quantity of nitrated products, direct nitration of aniline is not a practical procedure…. Because of the presence of the acetyl group, the reactivity of the ring is decreased, and as a result, oxidation of the ring by nitric acid does not take place easily.
Why, on the route to making nitroaniline P, did you have to start by converting aniline into acetanilide first? Wouldn’t it have been simpler to just nitrate the aniline directly?
Because aniline causes an undesirable side reaction, acetanilide is utilized as the reactant in the nitration process rather than aniline.
What results can be expected by nitrating aniline?
When aniline is directly nitrated with nitric acid, the resulting reaction produces a complex combination of mono-, di-, and trinitro compounds as well as oxidation products.
What are the steps involved in converting aniline to p-bromoaniline?
When aniline and acetic anhydride are heated together, acetanilide is produced. P-bromoacetanilide can be produced through treatment with bromine and acetic acid. The product of acidic or basic hydrolysis is p-bromoaniline.
How do you convert aniline to p dinitrobenzene?
- Nitration of aniline is the first step. The creation of para-nitroaniline is the consequence of the reaction between nitrous acid, aniline, and benzenamine. Sulfuric acid is also involved in this reaction.
- The formation of diazonium salt is the second step….
- Step 3: Synthesis of 1,4-dinitrobenzene.
What are the steps involved in converting aniline to fluorobenzene?
An indication is that aniline can be transformed into fluorobenzene by first converting aniline to benzene diazonium chloride and then converting fluorobenzene from the benzene diazonium chloride. The end result of the reaction will be the incorporation of a fluorine atom in place of the amine group that was previously present in the benzene ring.
Why is aniline considered to be meta-directing?
Because of resonance, the NH2 group in aniline is an ortho and para guiding group. This is because they will release electrons to the ring, but at the same time they will withdraw electrons from themselves because of a +1 impact from the aromatic ring…. When the contrary of what was expected occurs, the substituent in question is referred to as a meta directing group.
What results can be expected from the direct treatment of aniline with nitrating mixture?
An intricate mixture of mono-, di-, and tri-nitro compounds, as well as oxidation products, is produced by performing direct nitration of aniline with nitric acid. The p-isomer is the primary product that will be produced if the NH2 group is first protected by acetylation and then nitrated using a nitrating mixture.
Why is ammonia a more powerful basic substance than aniline?
As a result of the fact that ammonia is able to easily lose electron pairs while aniline is unable to do so, ammonia is believed to be a stronger base than aniline. An other interpretation of this phenomenon is that the lone pair of nitrogen atoms in aniline are in conjugation with the electrons that make up the benzene ring, and as a result, they participate in resonance.
What is the purpose of converting aniline to acetanilide?
What is the purpose of converting aniline to acetanilide prior to nitration? During the process of direct nitration, aniline is transformed into anilinium ion, which is a group that deactivates rings and directs meta groups. In light of this, the ortho/para directing group must be transformed into acetanilide in order for it to be preserved.
Why is ortho nitro aniline a relatively insignificant byproduct?
Observe that o-Nitroaniline is never the major product, and it remains the minor product in both of the reaction schemes 1 and 2. This is because the group provides steric hindrance at the ortho position, which makes it difficult to do nucleophilic substitution at the ortho position. The reason for this is given in the previous sentence.
What exactly are the products of tarry oxidation?
When aniline is not adequately protected during the nitration process, tarry oxidation products can result. This is because tarry oxidation products are a byproduct of nitric acid’s oxidation of aniline. In addition to the nitro derivatives, the direct nitration of aniline results in the production of tarry oxidation products.
What exactly is the composition of aniline?
The chemical formula for aniline is C6H5NH2, and it is an organic molecule. Aniline is the most basic form of aromatic amine, as it only consists of a phenyl group and an amino group connected to one another.
Why is acetylation performed on aniline prior to nitration?
The preservation of the amino group through acetylation allows the obstacles that stand in the way of the nitration of aniline to be overcome. Because of the presence of the acetyl group, the ring’s reactivity is decreased, and as a result, oxidation with nitric acid HNO3 does not take place easily.
How do you separate p-nitroacetanilide?
In order to extract pure p-nitroacetanilide from this mixture, the reaction mixture is recrystallized in ethanol. This causes the more readily soluble o-nitroacetanilide to dissolve in the ethanol, which allows for the extraction of pure p-nitroacetanilide from the mixture.
Is ortho-para aniline directional in aniline?
The aniline amino group directs in the ortho and para directions, but the aniline hydrogen chloride directs in the meta direction. The resonance structure of anilines suggests the development of a negative charge when they are in the ortho or para position.