Arene Diazonium Salts are More Stable Than Alkyl Diazonium Salts - Compounds Containing Nitrogen | Summary and Q&A

TL;DR

Arene diazonium salts are more stable than alkyl diazonium salts due to resonance and delocalization of electrons.

Key Insights

• 😋 Arene diazonium salts have a benzene ring attached to a diazonium or iso group, leading to their stability.
• 👥 The lone pair of electrons on the nitrogen in the diazonium group causes the delocalization of electrons.
• 😋 Resonance and delocalization of electrons stabilize positive charges generated around the benzene ring in arene diazonium salts.

Transcript

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Questions & Answers

Q: Why are arene diazonium salts more stable than alkyl diazonium salts?

Arene diazonium salts exhibit resonance and delocalization of electrons, which leads to the stabilization of positive charges around the benzene ring. This resonance and delocalization are not observed in alkyl diazonium salts, making them less stable.

Q: How does the structure of an arene diazonium salt contribute to its stability?

In an arene diazonium salt, the nitrogen in the diazonium group has a lone pair of electrons, making it more negative. This causes the electrons to be pulled towards it and delocalized around the benzene ring, resulting in the stabilization of positive charges.

Q: What happens to the positive charge in an arene diazonium salt?

The positive charge in an arene diazonium salt is delocalized and spread across the benzene ring through resonance and the delocalization of electrons. This delocalization of positive charge contributes to the stability of the molecule.

Q: Why do alkyl diazonium salts lack stability compared to arene diazonium salts?

Unlike arene diazonium salts, alkyl diazonium salts do not exhibit resonance and delocalization of electrons. As a result, there is no delocalization of positive charges, leading to their instability.

Summary & Key Takeaways

• Arene diazonium salts, which have a benzene ring attached to a diazonium or iso group, exhibit resonance and delocalization of electrons.

• The nitrogen in the diazonium group has a lone pair of electrons, making it more negative and causing the electrons to be pulled towards it.

• The delocalization of electrons results in the generation of positive charges around the benzene ring, making arene diazonium salts more stable than alkyl diazonium salts.