Chapter 14, Problem 14.66P

Treatment of ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CHCH}\left(\text{OH}\right){\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ with $\text{TsOH}$ affords two products (M and N) with molecular formula ${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}$. The ${}^1\text{H}\text{NMR}$ spectra of M and N are given below. Propose structures f or M and N and draw a mechanism to explain their formation.