What is the reason for these compounds to undergo Sn1 or Sn2 or both mechanisms?

1-chloropropanone(chloroacetone)
benzyl chloride
bromobenzene
bromocyclopentane
bromocyclohexane
2-bromobutane
2-chlorobutane
1-chlorobutane
2-chloro-2-methylpropane

1 Answer
Al E.
Apr 15, 2018

Let's look at the laundry list you've collected in a better format,

puu.sh

Every substrate you listed could generally undergoes a bimolecular nucleophilic substitution reaction, except #(3)#.

Moreover, the primary alkyl halides would undergo SN2, the secondary alkyl halides could undergo either SN1 or SN2 (esp. dependent on the other conditions), and the tertiary alkyl halide #(8)# could only undergo SN1.

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