How does the ratio of substitution product to elimination product formed from the reaction of propyl ­bromide with CH₃O⁻ in methanol change if the nucleophile is changed to CH₃S⁻?

Explain why only a substitution product and no elimination product is obtained when the following ­compound reacts with sodium methoxide:

a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both S_N2 and S_N1 reactions.

b. Can it undergo E2 and E1 reactions?

a. Assuming that the two compounds shown below have the same stability, which one would you expect to be more reactive in an S_N1 reaction?

b. Draw the products that each would form when the solvent is ethanol.

What products will be obtained from the E2 reaction of the following alkyl halides?

a.

What products will be obtained from the E2 reaction of the following alkyl halides?

b.

What products will be obtained from the E2 reaction of the following alkyl halides?

c.

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

a.

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

b.

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

c.

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

a. CH₃O⁻.

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

b. CH₃OH

Which compound is more reactive in an S_N1 reaction? In each case, you can assume that both alkyl halides have the same stability.

a.

b.

Why is a cumulated diene not formed in the reaction shown above?

What product is obtained when the following compound undergoes two successive elimination reactions?

What products are formed from the following reactions?

a.

What products are formed from the following reactions?

b.

Amines are good nucleophiles, even though they are neutral. How would the rate of an S_N2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?

a.

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?

b.

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?

c.

Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et₂O is diethyl ether.)

a.

b.

c.

Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et₂O is diethyl ether.)

d.

e.

Would you expect acetate ion (CH₃CO₂⁻) to be a better nucleophile in an S_N2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?

Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1-ethanol: in water or in 1.0 M HO⁻?

What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?

a.

b.

What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?

c.

d.

Identify the three products formed when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:

b. with H₂O?

After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?

a.

b.