Chapter 10, Problem 10.62P

Interpretation Introduction

Interpretation:

It is to be explained why the given Hofmann elimination reaction is slower than the one involving $\text{pentane-3-amine}$.

Concept introduction:

When amines are treated with excess iodomethane ${\text{(CH}}_{\text{3}}\text{I)}$ and silver oxide ${\text{(Ag}}_{\text{2}}\text{O)}$ and then heated to form the least substituted alkene as the major product, it is known as the Hofmann elimination reaction. The role of the reagent iodomethane is to convert the primary amine into trimethylamine as a bulkier group. In the stable conformation of cyclohexane, the chair form, bulkier group is stable at the equatorial position.

$\text{E2}$ reactions are favored when the H and the leaving group on the adjacent atom are anticoplanar.