Chapter 18, Problem 18.51P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be proposed.

Concept introduction:

The triple bond of the nitrile (CN) has two p bonds. Due to the electronegativity difference between carbon and nitrogen, this bond is polarized, which results in the partial positive charge on carbon and partial negative charge on nitrogen. Secondary amines act as bases as well as nucleophiles. Under the acidic condition, nitrogen of the nitriles is protonated, which makes the carbon of nitrile group more electrophilic. The alcohols are nucleophilic in nature.