Why does the presence of a nitro group make the benzene ring less reactive thanthe unsubstituted benzene ring? Explain
Question
Why does the presence of a nitro group make the benzene ring less reactive thanthe unsubstituted benzene ring? Explain
Solution 1
The presence of a nitro group makes the benzene ring less reactive than the unsubstituted benzene ring due to the following reasons:
-
Electron Withdrawing Nature: The nitro group (-NO2) is a strong electron-withdrawing group. This means it tends to pull electron density away from the benzene ring towards itself. This reduces the electron density in the benzene ring, making it less likely to participate in reactions that require it to donate electrons.
-
Resonance Effect: The nitro group is also a meta-directing group due to the resonance effect. In the resonance structures of nitrobenzene, the positive charge is located on the carbon atoms of the benzene ring. This makes the benzene ring less nucleophilic and therefore less reactive towards electrophilic aromatic substitution reactions.
-
Deactivation of the Ring: The overall effect of the nitro group is to deactivate the benzene ring. Deactivation refers to the reduction in reactivity of the benzene ring towards electrophilic aromatic substitution, which is the most common reaction of benzene.
In summary, the presence of a nitro group on a benzene ring makes it less reactive due to its electron-withdrawing nature, the resonance effect, and the deactivation of the benzene ring.
Solution 2
The presence of a nitro group makes the benzene ring less reactive due to the following reasons:
-
Electron Withdrawing Nature: The nitro group (-NO2) is a strong electron-withdrawing group. This means it tends to pull electrons towards itself due to its high electronegativity. This reduces the electron density in the benzene ring, making it less likely to participate in reactions that require an electron-rich site.
-
Resonance Effect: The nitro group can participate in resonance with the benzene ring. This further distributes the electron density away from the benzene ring, making it less reactive.
-
Inductive Effect: The nitro group also has a strong -I (negative inductive) effect, which means it pulls electrons away from the benzene ring through the sigma bonds. This further reduces the electron density in the benzene ring.
-
Deactivation of the Ring: The overall effect of these factors is that the benzene ring becomes deactivated, meaning it is less likely to undergo further reactions. This is why nitrobenzene is less reactive than benzene.
In summary, the presence of a nitro group on a benzene ring makes the ring less reactive due to the electron-withdrawing nature of the nitro group, its participation in resonance, its inductive effect, and the resulting deactivation
Similar Questions
Why is nitrobenzene 100,000 times less reactive than benzene toward nitration?Select answer from the options belowThe nitro group causes a higher energy of activation for nitration by destabilizing the sigma complex.The nitro group causes a higher energy of activation for nitration by significantly stabilizing the sigma complex.The nitro group causes a lower energy of activation for nitration by destabilizing the sigma complex.The nitro group causes a lower energy of activation for nitration by significantly stabilizing the sigma complex.
Correct statement about nitration reaction of benzene is
What is the difference between benzene ring and non benzene ring
Explain why the reactivity of group (vii) elements decreases down the group
Which of the following does not participate in the mechanism of nitration of benzene?Select answer from the options belowNO2+NO3+H2SO4 HNO3
Upgrade your grade with Knowee
Get personalized homework help. Review tough concepts in more detail, or go deeper into your topic by exploring other relevant questions.