Chapter 8, Problem 10PP

Interpretation Introduction

Interpretation:

The mechanism for the solvomercuration step of the ether synthesis and the use of solvomercuration-demercuration to prepare tert-butyl methyl ether is to be shown. The reason for the fact that $\text{Hg}{\left(\text{OAc}\right)}_2$ is less reactive than $\text{Hg}{\left({\text{O}}_2{\text{CCF}}_3\right)}_2$ is to be explained.

Concept Introduction:

Oxymercuration-demercuration: An organic reaction in which the double bonds of alkenes or alkynes are broken by $\text{HgOAc}$. In this reaction, the multiple carbon–carbon bond has been replaced by $\text{OH}$ group.

When $\text{HgOAc}$ is added to alkenes, they undergo oxymercuration-demercuration and form alcohols.

When the solvent molecule attack as a nucleophile, then the process is known as solvomercuration-demercuration and the reagent used is $\text{Hg}{\left({\text{O}}_2{\text{CCF}}_3\right)}_2$.