the less sterically hindered molecule is most likely to favor Sn2 reaction than Sn1 because the nucleophile can easily attack it and inversion of configuration will take place.
The more sterically hindered your molecule is, the more it will favor Sn1 because it forms a carbocation intermediate. The more hyperconjugative structures your carbocation will form, the more stable your molecule is. complete racemization takes place.