Chapter 16: Ethers, Epoxides and Sulfides
Synthesis of Sulfides
Reaction type: Nucleophilic Substitution (S
N
2)
Summary
Reagents : typically use NaOH as the base to generate the thiolate then add the alkyl halide.
Since the reaction is S
N
2, the halide should be methyl or primary.
The method is essentially the same as that used for oxygen ethers.
Thiols (pK
a
= 10) are so acidic hydroxide (pK
a
= 15.7) is sufficiently strong enough to obtain quantitative deprotonation.
Related Reactions
Williamson Ether synthesis
©
Dr. Ian Hunt
, Department of Chemistry
