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Nitration of 1,4 -dimethylbenzene (p-xylene) gives a single product having the molecular formula \(\mathrm{C}_{\mathrm{a}} \mathrm{H}_{9} \mathrm{NO}_{2}\) in high yield. What is this product?

Short Answer

Expert verified
The product is 2-nitro-1,4-dimethylbenzene.

Step by step solution

01

Understand 1,4-Dimethylbenzene (p-Xylene)

The compound 1,4-dimethylbenzene, also known as para-xylene or p-xylene, consists of a benzene ring with two methyl groups attached at the para positions (opposite sides) of the benzene ring. It is a symmetrical compound.
02

Determine the Nitration Reaction

Nitration typically involves the substitution of one hydrogen atom on an aromatic ring with a nitro group (-NO2). Given that p-xylene is symmetrical with two identical positions for substitution, the nitro group will most likely replace a hydrogen atom adjacent to one of the methyl groups due to steric and electronic effects.
03

Identify Substitution Site

In p-xylene, the electrons in the benzene ring and the methyl groups activate the ring making it more susceptible to nitration. The ortho positions (next to the methyl groups) are activated, thus one of these positions will most likely be substituted by the incoming nitro group.
04

Apply Molecular Formula Information

The resulting product from the nitration of p-xylene is stated to have the molecular formula \(\text{C}_9\text{H}_9\text{NO}_2\). The formula indicates that one of the nine hydrogen atoms (originally on the ring or methyl groups) is replaced by a nitro group.
05

Describe the Product

By substituting one of the ortho hydrogen atoms with a nitro group in p-xylene, the product formed is 2-nitro-1,4-dimethylbenzene. This maintains the molecular formula \(\text{C}_9\text{H}_9\text{NO}_2\) by adding one \(\text{NO}_2\) group to the compound.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Nitration
Nitration is an essential chemical process in organic chemistry. It involves introducing a nitro group (-NO2) into an organic compound. This process is often utilized in the production of explosives, dyes, and many pharmaceuticals. The nitro group consists of a nitrogen atom bound to two oxygen atoms.
In nitration, a common method used is to mix concentrated nitric acid (HNO3) with concentrated sulfuric acid (H2SO4) to create a nitrating mixture, also known as a nitronium ion (NO2+). This highly reactive ion facilitates the addition to aromatic rings.
During the nitration process, aromatic compounds are often the target due to their stable ring structure. The reaction usually takes place under controlled conditions to achieve the desired nitro compound. Being a substitution reaction, nitration can considerably change the reactivity and behavior of the original molecule.
Aromatic Compounds
Aromatic compounds, also known as arenes, are a class of compounds characterized by their stable ring structure and a delocalized type of chemical bonding. The most recognized example of an aromatic compound is benzene ( / C6H6 ), with its six carbon atoms arranged in a planar hexagonal ring. This structure, along with the delocalization of electrons across the ring, contributes to benzene’s high stability and resistance to addition reactions.
One significant feature of aromatic compounds is their ability to undergo substitution reactions, where one of the hydrogen atoms in the ring can be replaced by another atom or group. This property is due to the high electron density in the aromatic ring that attracts electrophiles. - **Examples of Aromatic Compounds:** - Benzene - Toluene - Xylene
This ability for substitution makes aromatic compounds incredibly versatile, finding applications in the creation of many synthetic compounds used in industries today.
Substitution Reactions
Substitution reactions are a fundamental type of reaction in organic chemistry where one atom or group of atoms is replaced by another in a molecule. In the context of aromatic compounds, such as benzene derivatives, these reactions are preferred due to the maintenance of the aromatic ring's stability.
In an electrophilic aromatic substitution (EAS), the aromatic compound exchanges a hydrogen atom for another group, like a nitro group in the nitration process. This occurs because the electron-rich aromatic ring attracts electrophiles. However, considering the high stability of the aromatic ring, these reactions often require specific conditions or catalysts to proceed. - **Types of Electrophilic Substitution Reactions:** - Halogenation - Nitration - Sulfonation
These reactions are pivotal in modifying aromatic compounds, making them key in the synthesis of various products. Nitration, specifically, is particularly significant due to the broad utility of nitro compounds in developing dyes, medications, and explosives.

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Most popular questions from this chapter

In an attempt to prepare propylbenzene, a chemist alkylated benzene with 1-chloropropane and aluminum chloride. However, two isomeric hydrocarbons were obtained in a ratio of \(2: 1\), the desired propylbenzene being the minor component. What do you think was the major product? How did it arise?

Choose the compound in each of the following pairs that reacts faster with sodium methoxide in methanol, and write a chemical equation for the faster reaction. (a) Chlorobenzene or \(o\) -chloronitrobenzene (b) \(o\) -Chloronitrobenzene or \(m\) -chloronitrobenzene (c) 4-Chloro-3-nitroacetophenone or 4 -chloro-3-nitrotoluene (d) 2-Fluoro-1,3-dinitrobenzene or 1-fluoro-3,5-dinitrobenzene (e) 1,4 -Dibromo-2-nitrobenzene or 1 -bromo- 2,4 -dinitrobenzene

Write a reasonable mechanism for the formation of cyclohexylbenzene from the reaction of benzene, cyclohexene, and sulfuric acid.

Write equations showing how you could prepare each of the following from anisole and any necessary organic or inorganic reagents. If an ortho, para mixture is formed in any step of your synthesis, assume that you can separate the two isomers. (a) \(p\) -Methoxybenzenesulfonic acid (b) 2-Bromo-4-nitroanisole (c) 4 -Bromo-2-nitroanisole (d) \(p\) -Methoxystyrene

Using benzene and any necessary organic or inorganic reagents, suggest efficient syntheses of (a) Isobutylbenzene, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (b) (2,2-Dimethylpropyl)benzene, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\)

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