Chapter 16: Ethers, Epoxides and Sulfides

Synthesis of Sulfides

Summary

• Reagents : typically use NaOH as the base to generate the thiolate then add the alkyl halide.
• Since the reaction is SN2, the halide should be methyl or primary.
• The method is essentially the same as that used for oxygen ethers.
• Thiols (pKa = 10) are so acidic hydroxide (pKa = 15.7) is sufficiently strong enough to obtain quantitative deprotonation.

• Williamson Ether synthesis