7. Substitution Reactions

The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with ­triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.

c. Which alkyl halide has the larger k_quinuclidine/k_{triethylamine} ratio?

Starting with an alkyl halide, how could the following compounds be prepared?

c. butylmethylamine

Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.

c. Show another S_N2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

c. 1-iodobutane

d. CH₃—(CH₂)₃—CN

Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.

e. CH₃—(CH₂)₃—C≡CH

f. CH₃CH₂—O—(CH₂)₃—CH₃

g. CH₃—(CH₂)₃—NH₂

Show how each compound might be synthesized by the SN2 displacement of an alkyl halide.

e. H₂C=CH—CH₂CN

f. H—C≡C—CH₂CH₂CH₃

Give two syntheses for (CH₃)₂CH—O—CH₂CH₃, and explain which synthesis is better.

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(a) F^- vs Br^-

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(b)

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(d)