Chapter 5, Problem 42P

(a) Assuming that the rate-determining elementary step in the reaction of $\text{trans-4-methylcyclohexanol}$ with hydrogen bromide is unimolecular, write an equation for this step. Use curved arrows to show electron flow.

b) Two stereoisomers of $\text{1-bromo-4-methylcyclohexane}$ are formed when $\text{trans-4-methylcyclohexanol}$ reacts with hydrogen bromide. Write a separate equation for the elementary step that gives each stereoisomer.