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

c. butylmethylamine

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

c. Cl⁻ or Br⁻

Rank the following from most reactive to least reactive in an E2 reaction:

Rank the following from most reactive to least reactive in an S_N1 reaction:

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

a. 3-bromo-2,2,3-trimethylpentane

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

b. 4-bromo-2,2,3,3-tetramethylpentane

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

c. 3-bromo-2,3-dimethylpentane

d. 3-bromo-3,4-dimethylhexane

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

d. 3-bromo-3,4-dimethylhexane

Which of following ethers cannot be made by a Williamson ether synthesis?

When 2-bromo-2,3-dimethylbutane reacts with a strong base, two alkenes (2,3-dimethyl-1-butene and 2,3-dimethyl-2-butene) are formed.

a. Which of the bases (A, B, C, or D) would form the highest percentage of the 1-alkene?

b. Which would give the highest percentage of the 2-alkene?

What are the products of the following reactions?

a.

b.

What are the products of the following reactions?

e.

What are the products of the following reactions?

f.

What are the products of the following reactions?

g.

h.

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

When the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation of these products.

cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.

Draw the substitution and elimination products.

a.

b.

tert-Butyl chloride undergoes solvolysis in both acetic acid and formic acid. Solvolysis occurs 5000 times faster in one of these two solvents than in the other. In which solvent is solvolysis faster? Explain your answer. (Hint: Formic acid is more polar than acetic acid.)

What substitution products are obtained when each of the following compounds is added to a solution of sodium acetate in acetic acid?

a. 2-chloro-2-methyl-3-hexene

b. 3-bromo-1-methylcyclohexene

Show how each of the following compounds can be synthesized from the given starting materials:

a. CH₃CH₂CH₂Br→CH₃CH₂CH₂CH₂CH₃

Show how each of the following compounds can be synthesized from the given starting materials:

b.

Show how each of the following compounds can be synthesized from the given starting materials:

c.

Show how each of the following compounds can be synthesized from the given starting materials:

d.

In which solvent—ethanol or diethyl ether—would the equilibrium for the following S_N2 reaction lie farther to the right?

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.

a.Which reaction had the larger rate constant?

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?

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?

Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structures of the ethers.