Chapter 9, Problem 51P

Interpretation Introduction

Interpretation: A stepwise detailed mechanism that illustrates formation of B and C products from A is to be drawn.

Concept introduction: The reaction of alcohols with halogen acids $\left(\text{HX}\right)$ is a general method to obtain $\text{1}\text{°}\text{,}\text{2}\text{°}\text{or}\text{3}\text{°}$ alkyl halides. This method is preferred due to the formation of ${\text{H}}_{\text{2}}\text{O}$ as leaving group. Both $2\text{°}$ and $3\text{°}$ alcohols undergo ${\text{S}}_{\text{N}}\text{1}$ mechanism to yield the desired alkyl halide. In case of secondary alcohols the carbocation rearrangement takes place through $\text{1, 2-shift}$ of hydrogen or methyl group.