Chapter 10, Problem 10.17P

Interpretation Introduction

Interpretation:

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

Concept introduction:

The alcohol is deprotonated in the presence of a strong base to form alkoxide. An ${\text{S}}_{\text{N}}\text{2}$ reaction between an alkoxide anion and an alkyl halide can also take place intramolecularly, yielding cyclic ethers. This type of reaction proceeds by a two-step mechanism. In the first step, the hydroxyl group is deprotonated to produce an alkoxide nucleophile. The second step is an intramolecular ${\text{S}}_{\text{N}}\text{2}$ reaction. The reaction is favored in large part by the formation of a five-membered ring, which tends to favor intramolecular reactions over intermolecular ones.