7. Substitution Reactions

Which of the following alcohols will most likely undergo substitution by an $S_{N}1$ mechanism in acidic conditions?

Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution: $\mathrm{amide}$, $\mathrm{ester}$, $\mathrm{acid}-\mathrm{chloride}$.

In the context of nucleophilic substitution reactions, which of the following is most likely to break a nitrogen-containing bond such as a $C–N$ bond in an alkylamine?

Which of the following best describes the outcome when the ${\mathrm{acetylide}}_{-}$ ion reacts with $\mathrm{CH}{3}_{}\mathrm{OH}$ in a nucleophilic substitution reaction?

Determine whether the following reaction is an example of a nucleophilic substitution reaction: ${\mathrm{CH}}_3{\mathrm{Br}}_1$ + ${\mathrm{OH}}_1$ → ${\mathrm{CH}}_3{\mathrm{OH}}_1$ + ${\mathrm{Br}}_1-$

For a certain nucleophilic substitution reaction, the rate of substitution is found to depend only on the concentration of the substrate and not on the concentration of the nucleophile. Which type of mechanism is most likely operating in this reaction?

Which of the following is the major product formed when $C_4{H}_9\mathrm{Br}$ (2-bromo-2-methylpropane) reacts with $C_4{H}_{9}OK$ (potassium t-butoxide) in ethanol?

Which of the following alkyl halides reacts fastest with trimethylamine in an $S_{\mathrm{N\; 2}}$ reaction?

Which of the following compounds can be prepared by reacting an alkyl iodide with a suitable nucleophile in a nucleophilic substitution reaction?

Which of the following reactions is classified as a nucleophilic substitution reaction?

Which of the following is the major organic product formed when $t_1-\mathrm{butyl} \mathrm{bromide}$ reacts with water in an $S{N}_1$ reaction? Ignore any inorganic byproducts.

When 1-bromopropane reacts with $NaCN$ in acetonitrile, which product is primarily formed?

In the context of nucleophilic substitution, consider the following molecule with labeled arrows indicating different atoms: Which arrow identifies the nucleophilic site in the molecule shown?

Rank the following electrophiles from most reactive (1) to least reactive (4) in an SN2 reaction: $\mathrm{CH}{3}_{\mathrm{Br}}$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{Br}}$, $\left(\mathrm{CH}{3}_2\right)\mathrm{CHBr}$, $\left(\mathrm{CH}{3}_3\right)\mathrm{CBr}$.

Which of the following alkyl halides is most likely to undergo rearrangement during reaction with ${\mathrm{CH}}^3\mathrm{OH}$?