7 Multiple Answer 2 points Which of the following alkyl bromide isomers would NOT undergo any nucleophilic substitution reactions? a) bromocyclobutane b) 4-bromo-1-butene c) 3-bromo-1-butene d) 1-bromo-1-butene e) All will react at the same rate. A B

The alkyl bromide isomer that would NOT undergo nucleophilic substitution is d) 1-bromo-1-butene. This is because the presence of a double bond at the first carbon makes it much more susceptible to elimination reactions rather than substitution, as the π bond can stabilize a carbocation which favors the loss of a leaving group rather than having a nucleophile attack. Regarding the others, bromocyclobutane, 4-bromo-1-butene, and 3-bromo-1-butene can undergo nucleophilic substitutions, albeit at varying rates. Bromocyclobutane can proceed through an SN2 mechanism given its accessible carbon. Meanwhile, 4-bromo-1-butene and 3-bromo-1-butene, with more substitution potential, can also participate in these reactions, although steric and double bond proximity may affect their reactivity.