This reaction will proceed via an $S_N1$.
Work Step by Step
1. Substrate - The carbon connected to the leaving group is connected to 3 other carbons, which makes the reaction only possible via $S_N1$. 2. Nucleophile - $ROH$ is a weak* nucleophile, which favors $S_N1$ reactions. *(You can consult the table on page 216) 3. Leaving group - "$Tosylate$": Good leaving group, which favors $S_N2$. 4. Solvent - Not mentioned: not a factor.