17.2: Reaction Mechanism

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General Reaction Mechanism for the Synthesis of Sulfide from a Thiol

Figure \(\PageIndex{1}\): Reaction mechanism of the synthesis of a sulfide from a thiol

Figure 1 shows the reaction mechanism of how a thiol reacts with a base and an alkyl halide to form a sulfide.

Reaction Mechanism

This is the mechanism of a thiol (a molecule containing an SH group) being used to form a sulfide. Because of the sulfur atom's size, the thiol group serves as a nucleophile for the proton transfer with a strong base (such as sodium hydroxide). As a result, a negatively charged intermediate is formed, as well as water and a metal cation (due to the break in the bond with the hydroxyl group). The intermediate goes through a SN2 reaction with an alkyl halide, where the intermediate bonds with the alkyl group to form a sulfide while the metal cation bonds with the halogen anion to form a halide.

References

Preparation of sulfides (video). https://www.khanacademy.org/science/...on-of-sulfides (accessed Mar 14, 2021).

Master Organic Chemistry LLC. Thiols And Thioethers. https://www.masterorganicchemistry.c...nd-thioethers/ (accessed May 2, 2021).

Contributor

Joshua Thielen