Consider the following reaction: 

1-chloro-1,3,4-trimethylcyclopentane + propan-1-ol →

Is its mechanism predominantly first order (S_N1) or second order (S_N2)? What is the expected substitution product? (Recall: The strength of the nucleophile (or base) usually dictates the order of the reaction. Weak nucleophiles often react by unimolecular first-order pathways, while strong nucleophiles promote bimolecular second-order reactions. Also, S_N1 is unlikely with 1° halides unless they are resonance-stabilized, while S_N2 is unlikely with 3° halides.)