Question: What is the mechanism of the nitration of benzene?
Options:
Electrophilic addition
Nucleophilic substitution
Electrophilic substitution
Radical substitution
Correct Answer: Electrophilic substitution
Solution:
The mechanism of nitration of benzene is electrophilic substitution, where the nitronium ion acts as the electrophile.
What is the mechanism of the nitration of benzene?
Practice Questions
Q1
What is the mechanism of the nitration of benzene?
Electrophilic addition
Nucleophilic substitution
Electrophilic substitution
Radical substitution
Questions & Step-by-Step Solutions
What is the mechanism of the nitration of benzene?
Step 1: Start with benzene, which is a stable ring of carbon atoms with hydrogen atoms attached.
Step 2: Prepare the nitrating agent, which is a mixture of concentrated nitric acid (HNO3) and concentrated sulfuric acid (H2SO4).
Step 3: The sulfuric acid helps generate the nitronium ion (NO2+), which is the active electrophile in this reaction.
Step 4: The nitronium ion (NO2+) approaches the benzene ring. Since it is positively charged, it is attracted to the electrons in the benzene ring.
Step 5: The nitronium ion forms a bond with one of the carbon atoms in the benzene ring, temporarily disrupting the ring's structure and creating a positively charged intermediate called a sigma complex.
Step 6: The sigma complex is unstable, so it quickly loses a hydrogen ion (H+) to restore the aromaticity of the benzene ring.
Step 7: The result is nitrobenzene, where one hydrogen atom on the benzene ring has been replaced by a nitro group (NO2).
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