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Step 7: The result is nitrobenzene, where one hydrogen atom on the benzene ring has been replaced by a nitro group (NO2).