Chapter 9, Problem 9.36P

Interpretation Introduction

Interpretation:

The complete and detailed intramolecular nucleophilic substitution reaction mechanism of the given substrate is to be drawn. The major product of the reaction is to be determined.

Concept introduction:

An ${\text{S}}_{\text{N}}\text{2}$ reaction is a unimolecular nucleophilic substitution reaction and is a single-step reaction. The nucleophile attacks on the opposite side of the leaving group. The substitution of the nucleophile and removal of the leaving group takes place in the same step. In the basic condition, the base acts as a nucleophile and abstracts the acidic proton from the substrate.

Generally, a chemical reaction takes place among two separate functional groups; instead of a separate molecule, they can be a part of the same molecule. They are attached to different places on the molecular backbone. This reaction, within the same molecule, is known as an intramolecular reaction. In intramolecular reaction, the nucleophile and the leaving group are on the same molecule resulting in the formation of a five or six-membered ring. The stability of the ring depends on the changes in the entropy and strain during the formation of the ring. The ring strain declines sharply to zero on going from a three-membered ring to a six-membered ring. Five or six-membered rings are more stable than the more membered ring.