Chapter 8.3, Problem 8.19P

Interpretation Introduction

Interpretation:

The hydroxide ion functions as a base or as a nucleophile in the given mechanistic step has to be identified.

Concept Introduction:

Nucleophile is the one which are capable of donating a pair of electrons.  The one which is capable of accepting a pair of electrons are known as electrophiles.  The atom that is poor in electron density is an electrophilic center.

The speed at which the nucleophile attacks an electrophile is known as nucleophilicity.  In other words, the measure of rate of reaction is known as nucleophilicity.  The measure of position of equilibrium is known as basicity.

Nucleophilicity and Basicity appear parallel to each other in many cases.  Water is a weak nucleophile and weak base.  Hydroxide ion is a strong nucleophile and strong base.  Hydroxide ion can function either as a base or as a nucleophile.  If the hydroxide ion removes a proton means then it is acting as a base.  If it attacks an electrophile means, then it is acting as a nucleophile.