Draw the substitution products for each of the following S_N2 reactions. If the ­products can exist as stereoisomers, show which stereoisomers are formed:

a. (3S,4S)-3-bromo-4-methylhexane + CH₃O^-

b. (3S,4R)-3-bromo-4-methylhexane + CH₃O^-

Draw the substitution products for each of the following S_N2 reactions. If the ­products can exist as stereoisomers, show which stereoisomers are formed:

c. (3R,4R)-3-bromo-4-methylhexane + CH₃O^-

d. (3R,4S)-3-bromo-4-methylhexane + CH₃O^-

Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

a. (2S,3S)-2-chloro-3-methylpentane + high concentration of CH₃O⁻

b. (2S,3R)-2-chloro-3-methylpentane + high concentration of CH₃O⁻

Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

c. (2R,3S)-2-chloro-3-methylpentane + high concentration of CH₃O^-

Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

d. (2R,3R)-2-chloro-3-methylpentane + high concentration of CH₃O^-

Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

e. 3-chloro-3-ethyl-2,2-dimethylpentane + high concentration of CH₃CH₂O^-

Draw the major elimination product that would be obtained from each of the following reactants with a strong base and with a weak base:

a.

Explain why the rate of the reaction of 1-bromo-2-butene with ethanol is increased if silver nitrate is added to the reaction mixture.

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

a. (3S,4S)-3-bromo-4-methylhexane + CH₃O⁻

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

b. (3R,4R)-3-bromo-4-methylhexane + CH₃O⁻

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

c. (3S,4R)-3-bromo-4-methylhexane + CH₃O⁻

Two elimination products are obtained from the following E2 reaction:

a. What are the elimination products?

b. Which is formed in greater yield?

Draw the structures of the products obtained from the following reaction:

How could you prepare the following compounds from the given starting materials?

b.

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

a. Why do they form the same elimination product?

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

b. Explain, by showing the mechanisms, why different substitution products are obtained.

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

c. How many stereoisomers does each of the elimination and substitution reactions form?

Draw the product of each of the following reactions:

1.

Draw the product of each of the following reactions:

2.

Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following alkyne:

CH₃CH₂C≡CCH₂CH₂CH₂CH₃

Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following ether:

Propose a mechanism for the following reaction:

Explain why tetrahydrofuran can solvate a positively charged species better than diethyl ether can.

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.)

Propose a mechanism for the following reaction.

What products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?

Predict the product for the following reaction and write a mechanism to explain how it is formed.

For each of the following compounds, draw the product that forms in an E2 reaction and indicate its configuration:

a. (1S,2S)-1-bromo-1,2-diphenylpropane

For each of the following compounds, draw the product that forms in an E2 reaction and indicate its configuration:

b. (1S,2R)-1-bromo-1,2-diphenylpropane

When equivalent amounts of methyl bromide and sodium iodide are dissolved in methanol, the concentration of iodide ion quickly decreases and then slowly returns to its original concentration. Account for this observation.