This is a question our experts keep getting from time to time. Now, we have got the complete detailed explanation and answer for everyone, who is interested!
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.
During the process of nitration, which reagent is utilized to protect the amino group on the aniline molecule?
SOCl2 / Pyridine.
What is the final product when aniline is nitrated prior to being protected from the elements?
As a consequence of this, the nitration of aniline results in the production of both products of the nitration reaction as well as some products of the oxidation reaction. However, if the nitration of aniline is carried out in an environment with strict control over the variables, then p-nitroaniline and m-nitroaniline will emerge as the primary products.
What results from putting aniline through the nitration process?
When nitration occurs in aniline, the Nitric Acid causes the aniline to become protonated, which results in the formation of the Anilinium ion. So, because the nitrogen atom does not possess a lone pair with which to conjugate, it does not have a mesomeric influence on the ring. But, because nitrogen is now protonated, it has a large negative inductive effect.
Why does nitration of aniline result in the formation of a meta product?
The presence of the anilinium group, which does not have a free electron pair anymore (since it is bound to the H+), deactivates the aromatic ring in the direction of electrophilic substitution. This results in the formation of anilinium ion, which is meta directive. Hence, nitration of aniline results in the formation of the meta derivative in addition to the ortho and para derivatives.
The amino group is shielded by nitrogen during the process of nitration of aniline.
We found 39 questions connected to this topic.
Why is nitration of aniline such a challenging process?
The transformation of aniline into protonated aniline makes nitration of aniline a challenging process to perform. 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.
Why does aniline give nitroaniline when combined with M?
Because aniline can be nitrated in an environment with a high concentration of acid, m-nitroaniline can also be produced. Regardless of the presence of substituents, the nitro group will always migrate to the m-position…. Aniline is found as the anilinium ion in an environment that is highly acidic. When there are no other groups present, the nitro group will always move into the m-position.
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….
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.
Can aniline be considered an electrophile?
The process of forming acetanilide through a nucleophilic replacement reaction with acetic anhydride is known as acetylation. Aniline is the term used to refer to the product of this reaction. In this reaction, aniline plays the role of the nucleophile, while the acetic anhydride group acyl (CH3CO-) performs the role of the electrophile.
The nitration of acetanilide results in the production of which product in the greatest quantity?
Acetanilide also demonstrates reagent-dependent orientation in the nitration process. Nitric and sulfuric acids produce paranitroacetanilide as the primary product, whereas nitric acid combined with acetic anhydride favors ortho-nitration.
How did P-nitroacetanilide become the predominant form of the product?
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.
Why is it necessary to preserve the amino group in aniline before carrying out nitration?
Answer: The obstacles that stand in the way of the nitration of aniline can be solved by protecting the amino group through the process of acetylation. 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.
The nitration of aniline is performed after acylation for the following reason:
(a) The -NH2 group becomes active as a result of acylation. (c) It is beneficial to the oxidation process.
The answer to this question is the substance that results from brominating aniline while conserving NH2.
The primary product obtained from brominating acetanilide with bromine and then hydrolyzing the mixture with acid is p-bromoaniline.
Why does aniline have an ortho-para configuration?
The NH2 group in aniline is an ortho and para directing group because it has the ability to realese electrons toward the ring as a result of resonance while at the same time it has the ability to withdraw electrons toward itself from the aromatic ring as a result of the +1 effect. The resonant structure of aniline demonstrates the development of a negative charge in the ortho and para positions.
Does NO2 engage in meta-directing?
A quick examination of the resonance structures reveals that the positive charge becomes concentrated at the ortho-para locations because NO2 is an electron-withdrawing group. This may be seen by looking at the resonance structures. Because of this, the potential for electrophilic aromatic substitution at these sites is eliminated. As a result, NO2 is a meta-director, as was covered in all of our organic chemistry classes.
Is Cho using a meta-style of directing?
The answer, along with an explanation: Because of its electron-withdrawing property, the aldehyde group (-CHO) in benzaldehyde functions as a meta-director in the benzaldehyde molecule.
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 does the pKb value for aniline come out to be higher than that of methylamine?
(i) The lone pair of electrons that are found on the N atom of aniline are distributed over the benzene ring in aniline. As a direct consequence of this, the number of electrons surrounding the nitrogen atom becomes less dense… As a consequence of this, aniline is a less effective base than methylamine. Because of this, the value of its pKb is greater than that of methylamine.
Why is nitration of acetanilide not the same as nitration of aniline?
Image text transcribed as follows: Because aniline causes an undesirable side reaction, acetanilide is substituted for it in the nitration process rather than aniline. A diazonium salt is produced as a byproduct of the third reaction; however, this product is not isolated but rather put to use right away.
What is meant by the term “aniline acetylation”?
Aniline, also known as phenylamine, is a primary amine that has a basic chemical make-up… The reaction known as acetylation occurs when acetic anhydride combines with aniline. This results in the formation of acetanilide via a nucleophilic substitution reaction. Aniline plays the role of the nucleophile in this reaction, whereas the acyl (CH3CO-) group derived from acetic anhydride takes on the role of the electrophile.
What steps are involved in the production of nitro substituted products using aniline?
2) An aromatic electrophilic substitution involving aniline and the electrophile in question. 3) Re-formation of the sulfuric acid catalyst through deprotonation of the para hydrogen by the anion HSO4-. The amino group can point either orto or para, and because of this, the nitro group will be inserted primarily in the para position. Steric constraints are the primary reason for this.
Why is the temperature kept so low throughout the nitration process?
In the process of nitration, the reaction that occurs with methylbenzene is approximately 25 times faster than the one that occurs with benzene. In order to stop the substitution of more than one nitro group, you would need to work at a lower temperature, which in this case would be 30 degrees Celsius rather than 50 degrees Celsius.