Chapter 10, Problem 10.61P

Interpretation Introduction

Interpretation:

The complete detailed mechanism with the major product for the given reaction is to be drawn.

Concept introduction:

An amine with a poor leaving group is converted into a tetra alkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like ${\text{CH}}_{\text{3}}\text{I}$. Subsequent treatment with ${\text{Ag}}_{\text{2}}\text{O}$ followed by heat induces elimination. The bulkiness of the leaving group in the tetra alkyl ammonium ion causes the anti-Zaitsev regiochemistry.