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

c.

Draw the products of the following intramolecular reactions:

a.

b.

Draw the products of the following intramolecular reactions:

c.

d.

Draw the products of the following intramolecular reactions:

e.

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

a.

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

b.

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

c.

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

d.

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

c. CH₃S⁻

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

d. HS⁻

Which member of each pair is a better nucleophile in methanol?

e. I⁻ or Br⁻

f. Cl⁻ or Br⁻

Which member in each pair in [PROBLEM 9-68] is a better leaving group?

a. H₂O or HO⁻

b. NH₃ or H₂O

Which member in each pair in [PROBLEM 9-68] is a better leaving group?

c. H₂O or H₂S

d. HO⁻ or HS⁻

Which member in each pair in [PROBLEM 9-68] is a better leaving group?

e. I⁻ or Br⁻

f. Cl⁻ or Br⁻

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

a.

b.

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

e.

f.

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

g.

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

h.

Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.

a. The concentration of both the alkyl halide and the nucleophile are tripled.

b. The solvent is changed to ethanol.

Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.

c. The alkyl halide is changed to 1-chlorobutane.

d. The alkyl halide is changed to 2-bromobutane.

Explain how the following changes affect the rate of the reaction of 2-bromo-2-methylbutane with methanol:

a. The alkyl halide is changed to 2-chloro-2-methylbutane.

b. The alkyl halide is changed to 2-chloro-3-methylbutane.

Starting with cyclohexene, how can the following compounds be prepared?

a. methoxycyclohexane

Starting with cyclohexene, how can the following compounds be prepared?

b. cyclohexylmethylamine

Starting with cyclohexene, how can the following compounds be prepared?

c. dicyclohexyl ether

Rank the following species in each set from best nucleophile to poorest nucleophile.

a.

Rank the following species in each set from best nucleophile to poorest nucleophile.

b.

Rank the following species in each set from best nucleophile to poorest nucleophile.

c. H₂O and NH₃ in methanol

d. Br⁻, Cl⁻, I⁻ in methanol

The pK_a of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pK_a? Why?

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

b. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. (R)-2-bromopentane+CH₃O⁻

b. (R)-3-bromo-3-methylheptane+CH₃OH