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?

a. 2-methoxybutane

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

b. 1-methoxybutane

2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations:

b. Both trans reactants form the same racemic mixture.

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.

b. The same experiment was done using isopropyl iodide instead of methyl iodide. Which reaction had the larger rate constant?

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.