Chapter 10, Problem 10.65P

Interpretation Introduction

Interpretation:

The structure of the initial amine, whose molecular formula is ${\text{C}}_{\text{9}}{\text{H}}_{\text{13}}\text{N}$, is to be drawn for the given reaction.

Concept introduction:

In the Hoffman elimination, an amine with a poor leaving group is converted into a good leaving group, tetraalkyl ammonium ion, which is a moderately good leaving group, using excess of an alkyl halide (usually ${\text{CH}}_{\text{3}}\text{I}$). The bulkiness of the leaving group causes a anti-Zaitsev product or Hoffman product. It generates the least substituted alkene as the major product. The carbon atom to which the primary amine group is attached must be the secondary carbon with at least one alpha hydrogen atom.