Chapter 20.SE, Problem 26MP

Interpretation Introduction

Interpretation:

A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt, is to be given using curved arrows to show the flow of electrons at each step, is to be proposed.

Concept introduction:

The Pinner reaction takes place through the steps given. i) Protonation of the nitrile ii) Nucleophilic attack of the alcohol on the protonated nitrile iii) proton transfer from oxygen to nitrogen iv) Nucleophilic attack by water on the protonated amine v) Elimination of a proton by water vi) Elimination of ammonia.

To propose:

A mechanism for the Pinner reaction shown, in which a nitrile is converted to an ester through an iminoester salt using curved arrows to show the flow of electrons at each step.