Homolytic and Heterolytic Bond Cleavages | Summary and Q&A

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February 18, 2023
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Homolytic and Heterolytic Bond Cleavages

TL;DR

Homolytic bond cleavage occurs when each atom in the bond takes one electron, while heterolytic bond cleavage occurs when one atom takes both electrons.

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Questions & Answers

Q: What is the difference between homolytic and heterolytic bond cleavage?

Homolytic bond cleavage occurs when each atom in the bond takes one electron, while heterolytic bond cleavage occurs when one atom takes both electrons from the bond.

Q: What types of reactions do homolytic bond cleavage typically occur in?

Homolytic bond cleavage is common in radical reactions.

Q: What happens during heterolytic bond cleavage?

In heterolytic bond cleavage, one atom takes both electrons from the bond, resulting in a positive charge on one atom and a negative charge on the other.

Q: How does hydroxide behave in the SN2 reaction?

In the SN2 reaction, hydroxide acts as a nucleophile and attacks the partially positive carbon atom, causing heterolytic bond cleavage.

Summary & Key Takeaways

  • Homolytic bond cleavage occurs in radical reactions, where each atom takes one electron from the bond.

  • Heterolytic bond cleavage occurs when one atom takes both electrons from the bond, resulting in a carbocation and a negative ion.

  • Hydroxide can act as a nucleophile in the SN2 reaction or as a base in the deprotonation of an alpha hydrogen.

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