Chapter 17, Problem 17.68P

Interpretation Introduction

Interpretation:

When carbon disulfide (${\text{CS}}_{\text{2}}$) is treated with an alcohol in the presence of abase, the product is a xanthate salt. If an alkyl halide is also present, a xanthate ester is formed. A mechanism for each of these reactions is to be proposed.

Concept introduction:

To convert the weak nucleophile ROH into strong nucleophile ${\text{RO}}^{\text{-}}$ via proton transfer, the strong base like NaOH can be used. The carbon atom in ${\text{CS}}_{\text{2}}$ is electron-poor and the nucleophilic addition of an alkoxide ion gives a salt as a product. This salt is can be converted to ester via ${\text{S}}_{\text{N}}\text{2}$ step by using alkyl halide.