More Practice on SN1 and SN2 reactions with mechanism (15 plus examples) 

It does have resonances and that is why it goes SN1. Carbocation at benzylic position is stabilized by resonances.

why is there no resonance for the problem with OTs?

Hello Sir. For 16:17, if we convert the conformation chair form to cyclohexane form, it seems that our carbon bonding with --OH group is achiral, so I assume there is only one product? How come we have two? Sorry I have so many questions :( thank you in advance