Nitration of Benzene Mechanism - Electrophilic Aromatic Substitution Reactions | Summary and Q&A

TL;DR

This video explains the mechanism of the nitration of benzene, where a hydrogen atom is replaced with an electrophile, resulting in the formation of nitrobenzene.

Key Insights

• 🫀 Nitration of benzene involves replacing a hydrogen atom with an electrophile, resulting in the formation of nitrobenzene.
• 😑 The reaction requires nitric acid and sulfuric acid to generate the electrophile, nitronium ion.
• 😑 Protonation of nitric acid with sulfuric acid helps in creating the nitronium ion.
• 💁 The attack of the benzene ring on the nitronium ion leads to the formation of nitrobenzene.
• 😋 The regenerating of the aromatic ring is facilitated by a base, which removes the carbocation.
• ❓ The mechanism is an example of electrophilic aromatic substitution.
• 💦 Water can be used as a base in the last step or even the solvent itself.

Transcript

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Questions & Answers

Q: What are the reagents used in the nitration of benzene?

The reagents used are nitric acid and sulfuric acid. Nitric acid is protonated with sulfuric acid to generate the electrophile, nitronium ion.

Q: What is the purpose of sulfuric acid in this reaction?

Sulfuric acid helps nitric acid generate the electrophile by protonating it and converting the OH group into a good leaving group, allowing the formation of the nitronium ion.

Q: How is the electrophile generated in the mechanism?

The electrophile, nitronium ion, is generated by protonating nitric acid with sulfuric acid. The OH2 group with a positive charge is then used to expel water, resulting in the formation of the nitronium ion.

Q: What happens after the benzene ring attacks the nitronium ion?

After the benzene ring attacks the nitronium ion, one of the pi bonds in benzene breaks, resulting in the formation of nitrobenzene. The nitrogen atom in the nitronium ion remains bonded to two oxygen atoms.

Summary & Key Takeaways

• The video discusses the reaction of benzene with nitric acid and sulfuric acid, resulting in the substitution of a hydrogen atom with an electrophile, NO2.

• It explains the process of generating the electrophile by protonating nitric acid with sulfuric acid, which helps to create the nitronium ion.

• The benzene ring attacks the nitronium ion, breaking one of the pi bonds and forming nitrobenzene. The final step involves regenerating the aromatic ring using a base.