Chapter 17, Problem 17.9P

Interpretation Introduction

Interpretation:

A complete and detailed mechanism for the reactions in Equation 17-14 is to be drawn.

Concept introduction:

Lithium aluminum hydride (${\text{LiAlH}}_{\text{4}}$) is a strong reducing agent. It is a common hydride source in organic chemistry. $\text{H}$ has a partial negative charge because it is covalently bonded to a less electronegative atom. The hydride anion is extremely reactive, both as a nucleophile and as a base.

${\text{LiAlH}}_{\text{4}}$, as a source of very strong ${\text{H}}^{-}$ nucleophile, adds up twice to the triple bond of nitrile. Subsequently, the ${\text{N}}^{\text{2-}}$ is protonated twice, producing a primary amine.