Chapter 22.9, Problem 5LTS

Interpretation Introduction

Interpretation: The major product is to be found when 3-methyl-3-hexanamine is treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are given and used as the reaction conditions in the given reactions.  This reaction is called Hofmann elimination.  The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternary ammonium salt which is a excellent leaving group.  After treatment with strong base, aqueous silver oxide and heat, quaternary ammonium salt gives alkenes.  Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

To find: Get the major product of 3-methyl-3-hexanamine in Hofmann elimination

Identify all α- and β-positions in the given amine compound