Chapter 20, Problem 20.6P

Interpretation Introduction

Interpretation:

The product of the sequence of reactions shown is to be predicted.

Concept introduction:

This is a Gabriel synthesis, which yields a primary amine from an alkyl halide and gives phthalate as a by-product. The aromatic $\text{C-Br}$ is inert to these reaction conditions. The sp³- Carbon of the ${\text{CH}}_{\text{2}}\text{-Br}$ bond is the electrophilic $\text{C}$ atom susceptible to nucleophilic attack. The Gabriel synthesis produces only the intended primary amine.