7. Substitution Reactions

Consider the compound ${\mathrm{CH}}_{3}OH$. Which of the following would be considered a nucleophilic site?

Which of the following is the best nucleophile in ${\mathrm{CH}}_3\mathrm{OH}$ (methanol) solvent?

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

The reaction of an alkyl chloride with potassium iodide is generally carried out in acetone to maximize the amount of alkyl iodide that is formed. Why does the solvent increase the yield of alkyl iodide? (Hint: Potassium iodide is soluble in acetone, but potassium chloride is not.)

Which alkyl halide is more reactive in an E2 reaction with hydroxide ion: $1-\text{bromopropane}$ or $2-\text{bromopropane}$?

Given ${\mathrm{CH}}_3\mathrm{Br}$ (bromomethane) as the starting compound, which set of reagents and conditions will best yield ${\mathrm{CH}}_3\mathrm{CN}$ (acetonitrile) via nucleophilic substitution?

When (R)-3-chloro-3-methylhexane is treated with methanol and heat, which of the following best describes the major product and the mechanism of the reaction?

Which of the following best describes the reaction when $\mathrm{pyridine}$ reacts with ${\mathrm{OH}}^{-}$ by nucleophilic aromatic substitution?

Which type of nucleophilic substitution mechanism is characterized as a single-step, bimolecular reaction?

Which of the following statements best describes the mechanism that occurs when a primary alkyl halide reacts with a strong nucleophile in a nucleophilic substitution reaction?

Which of the following is the major product of an $S_{N1}$ reaction of 2-bromo-2-methylpropane with water?

Which of the following alkyl halides would be most reactive in an $S{N}_2$ reaction?

Which of the following alkyl halides would proceed with the fastest rate in an $S{N}_2$ reaction?

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?