Chapter 14, Problem 14.58P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The conjugate bases of weak acids like alcohol can behave as both a strong base and a good nucleophile. In poar aprotic solvents, a secondary alkyl halide with good leaving group can undergo both nucleophilic substitution (${\text{S}}_{\text{N}}\text{2}$) and elimination (E2). The temperature at which the reaction is carried out determines which mechanism is favored and, therefore, the major product that is formed. A low temperature favors substitution while high temperatures favor elimination.