18 Sulfides

13.8 Sulfides | Organic Chemistry

Introduction

This lesson covers sulfides, including their naming, synthesis, and reactions. Sulfides, the sulfur equivalent of ethers, are relatively minor in terms of importance in organic chemistry and may not be covered in all courses.

Main Points

• Naming Sulfides:

- Similar to ethers, sulfides have a sulfur atom between carbon chains.

- The parent chain is named based on the longer side, and the substituent combines the alkyl part with the "thio" prefix (e.g., methylthiopropane).

• Synthesis of Sulfides:

- The primary method is via an SN2 reaction, using a nucleophile that contains sulfur.

- Commonly, sodium sulfide is used to replace a leaving group with a sulfur-containing group, forming a sulfide.

• Reactions of Sulfides:

- Alkylation: Sulfides can undergo SN2 reactions with alkyl halides, adding an alkyl group to the sulfur atom.

- Oxidation: Sulfides can be oxidized to sulfoxides and further to sulfones. Various oxidizing agents can be used, and typically, more robust conditions are required to go from sulfoxide to sulfone.

Conclusion

Sulfides, due to their strong nucleophilicity, participate in alkylation and oxidation reactions, making them useful in specific organic synthesis contexts. The synthesis and reaction processes are straightforward, involving standard SN2 mechanisms and common reagents.