7. Substitution Reactions

Which nucleophile could be used to react with butyl iodide to prepare ${\mathrm{CH}}_3\mathrm{CH}-\mathrm{CH}-{\mathrm{CH}}_2\mathrm{OCH}{3}_{}$ (butyl methyl ether)?

What is the product of the reaction of bromoethane with each of the following nucleophiles?

a. CH₃CH₂CH₂O⁻

b. CH₃C≡C⁻

In the context of nucleophilic substitution, what is the main purpose of treating an alcohol with tosyl chloride before reacting it with a nucleophile?

In nucleophilic substitution reactions, consider the following pairs of elimination reactions: (1) $E_1$ vs. $E_2$ in a tertiary alkyl halide, and (2) $E_1$ vs. $E_2$ in a primary alkyl halide. For each pair, which elimination reaction is generally faster?

Which of the following is the correct organic product of the $S_{\mathrm{N}}2$ reaction between $\mathrm{CH}{3}_2\mathrm{CHBr}$ (2-bromopropane) and $\mathrm{NaOH}$ in aqueous solution?

Which of the following would not result in an S$N_1$ reaction termination?

In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?

Classify the following solvents as favoring either $S{N}_1$ or $S{N}_2$ reactions: water, acetone, methanol, and dimethyl sulfoxide (DMSO). Which option correctly matches each solvent to the type of nucleophilic substitution it favors?

Predict the product of the following substitution/addition reactions involving phenoxides. [Because this problem represents a review of current and previous material, section numbers have been provided for your reference.]

(d)

Cardura, a drug used to treat hypertension, is synthesized as shown here.

a. Identify the intermediate (A) and show the mechanism for its formation.

Strawberry growers have used large quantities of methyl bromide (b.p. 4 °C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43 °C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?

Draw all the products of the following reaction: