Chapter 22, Problem 22.12YT

Interpretation Introduction

Interpretation:

Diazonium ions can be produced from primary alkylamines, ${\text{R-NH}}_{\text{2}}$, when treated with ${\text{NaNO}}_{\text{2}}$ under acidic condition, but the resulting alkyldiazonium ions are generally much too reactive to be useful intermediates in Sandmeyer reactions. The alkyldiazonium ion that would be produced from ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}{\text{CHNH}}_{\text{2}}$ is to be drawn. Why it is less stable than the benzenediazonium ion is to be explained.

Concept introduction:

The alkyldiazonium ion and benzenediazonium ion both possess the ${\text{N}}_{\text{2}}{}^{\text{+}}$ group, which can behave as an excellent leaving group and depart as $\text{N}$ (g). These are produced by diazotization reaction. The diazotization is a chemical process that forms diazonium salt from corresponding primary amine.