7. Substitution Reactions

Which of the following alkyl halides is most likely to undergo solvolysis via an $S{N}_1$ mechanism?

In a nucleophilic substitution reaction of ${\mathrm{CH}}_3\mathrm{CH}\left(\mathrm{Br}\right)\mathrm{CH}$₂CH₃ with hydroxide ion, what minor product would form if no carbocation rearrangement occurred?

Which type of nucleophilic substitution mechanism is most likely when an alkyl bromide reacts with hydroxide ion in a polar aprotic solvent?

Which of the following is the major substitution product formed when ${\mathrm{CH}}_3\mathrm{Br}$ reacts with aqueous $\mathrm{NaOH}$ in a nucleophilic substitution reaction?

Which of the following is a substitution reaction?

In nucleophilic substitution, the mechanism for the alkylation of terminal alkynes involves which key step?

In an $S{N}_2$ reaction, which molecular orbitals act as the HOMO and LUMO during the nucleophilic attack?

Which of the following is the major organic product when ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{Br}$ reacts with aqueous $\mathrm{NaOH}$ in a nucleophilic substitution reaction?

During the proton transfer step of a Friedel-Crafts alkylation reaction, which species typically acts as the base to remove a proton from the arenium ion intermediate?

Given the following alkyl halides, order them from fastest to slowest in terms of their reactivity toward an $S{N}_2$ reaction (1 = fastest): $\mathrm{CH}{3}_{\mathrm{Br}}$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{Br}}$, $\left(\mathrm{CH}{3}_2\right)\mathrm{CHBr}$, $\left(\mathrm{CH}{3}_3\right)\mathrm{CBr}$.

Which type of nucleophilic substitution reaction is most likely to occur when pyrimidine dimers in DNA are repaired, potentially leading to mutations that can cause cancer?

Rank the following alkyl halides in order of increasing reactivity in an $S{N}_2$ reaction: $\mathrm{CH}{3}_{\mathrm{Br}}$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{Br}}$, $\left(\mathrm{CH}{3}_2\right)\mathrm{CHBr}$.

Which of the following is the correct product of the nucleophilic substitution reaction between ${\mathrm{CH}}_3\mathrm{Br}$ and $\mathrm{OH}-$ in aqueous solution?

Which alkyl halide readily reacts with $NaI$ in acetone to undergo a nucleophilic substitution reaction?

Which of the following compounds is the least reactive toward $\mathrm{nucleophilic} \mathrm{addition}-\mathrm{elimination} \mathrm{reactions}$?