Chapter 9, Problem 9.54P

Interpretation Introduction

Interpretation: A step wise, detailed mechanism for the given reaction is to be stated.

Concept introduction: Alcohols undergo dehydration reaction in the presence of strong acids like ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ or $\text{p-toluenesulfonic}\text{acid}\left(\text{TsOH}\right)$ and yield alkenes. The mechanism of the reaction involves three steps. The first step is protonation of the oxygen atom to convert poor leaving group into good leaving group. The second step is heterolysis cleavage of $\text{C}-\text{O}$ bond to form a carbocation intermediate. The third step is abstraction of proton from a carbon adjacent to the carbocation to form desired product.