For SN1 reactions it’s important to have a good leaving group because this reaction occurs in two steps. Because alcohol is such a poor leaving group it needs to be helped by silver nitrate to help promote the ionization of the alkyl halide. This helps form the products of the SN1 reaction.
2-chlorobutane
This reaction didn’t occur because the carbocation isn’t stable enough for an SN1 reaction.
2-bromobutane
This reaction occurred in 32 seconds. This reaction occurred quickly because the carbocation was stabilized by the silver nitrate which favors SN1 reaction.
1-chlorobutane
This did not react because the carbocation needed wasn’t stable enough to react via SN1
1-bromobutane
This reacted in 4:22 however I don’t believe it occurred via SN1. Because none of the aspects of this reaction favor SN1.
2-chloro-2-methylpropane
This reaction occurred instantly because this chemical is a tertiary alkyl halide which is conducive for an SN1 reaction and there wasn’t any steric hindrance. The carbocation is stabilized by the silver nitrate.
Crotyl Chloride
This reaction occurred in 5 seconds because this chemical is resonance stabilized therefore produces a stable carbocation which favors SN1.
Benzyl Chloride
This reaction occurred in 2:09 because this chemical is resonance stabilized therefore produces a stable carbocation which favors SN1.
Bromobenzene
This did not react because bromobenzene produces and unstable carbocation.
Bromocyclohexane
This reacted in 10 seconds because bromocyclohexane is secondary bromine, and has steric strain, since it is a cyclic compound. The bigger steric in a molecule, the harder it is for the nucleophile to attack the leaving group (-Br) from the opposite sides, therefore, SN2 reaction is slower than SN1 for bromocyclohexane
Bromocyclopentane
This reacted instantly because bromocyclopentane is secondary bromine, and have bigger steric strain than bromocyclohexane, since it is a cyclic compound. The