Chapter 9, Problem 47P

Interpretation Introduction

Interpretation:

Whether methoxide ion is a better nucleophile in $C{H}_{3}OH$ or in DMSO has to be explained.

Concept Introduction:

Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.  When the negatively charged species is placed in aprotic solvent, the solvent molecules arrange themselves with their partially positively charged hydrogens pointing towards the negatively charged species.  The interaction between the ion and the dipole of the protic solvent is called an ion-dipole interaction