Chapter 10, Problem 10.76P

Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then

undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with $\text{TsOH}$ forms Α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, ${\text{HSO}}_{\text{3}}\text{Cl}$ forms a constitutional isomer, Α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile-a carbocation-to a double bond.