Chapter 9, Problem 9.1YT

Interpretation Introduction

Interpretation:

Which of the two reactions shows ammonia acting as a base and which one shows it acting as a nucleophile is to be determined.

Concept introduction:

An electron-rich species such as an atom with a lone pair can act as both a base and as a nucleophile. Whether it acts as a base or as a nucleophile depends on the atom to which it donates its lone pair. When the lone pair is used to form a bond with a proton (${\text{H}}^{\text{+}}$), the species is acting as a base. When the lone pair is used to form a bond with any electron-deficient atom other than a hydrogen, the species is acting as a nucleophile.