Chapter 9, Problem 9.76P

Interpretation Introduction

Interpretation: A stepwise mechanism for the dehydration of ${\text{CH}}_{\text{3}}{\text{CH}}_2{\text{CH}}_2{\text{CH}}_2\text{OH}$ with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ to form a mixture of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{CH}={\text{CH}}_{\text{2}}$, and the cis and trans isomers of ${\text{CH}}_{\text{3}}\text{CH}={\text{CHCH}}_{\text{3}}$ is to be drawn.

Concept introduction: The dehydration of $\text{1}\text{°}$ alcohols with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ does not involve the formation of $\text{1}\text{°}$ carbocation. However, the rearrangement of carbocation is possible even though no primary carbocation is formed, due to occurring of $\text{1, 2-shift}$ as the $\text{C}-{\text{OH}}_{\text{2}}{}^{+}$ bond is broken.