Question

By taking a suitable example, write the mechanism of the reaction of a thiol with an alkyl halide. Explain why thiols react more rapidly than open chain ethers.

Answer 1

Mechanism of the reaction of a thiol with an alkyl halide:

Thiols are more nucleophilic than open chain ethers. Nucleophility refers to the ability of an atom to donate a lone pair to an electrophile other than H. Sulphur, being less electronegative than oxygen, "holds on" to its electrons less tightly and thus donate its lone pairs more readily.