Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

c.

d.

The following three nitrogen mustards were studied for possible clinical use. One is now used clinically, one was found to be too unreactive, and one was found to be too insoluble in water to be injected intravenously. Which is which? (Hint: Draw resonance contributors.)

Why is melphalan a good cancer drug?

What is the product of each of the following reactions?

a.

What is the product of each of the following reactions?

c.

d.

What is the product of each of the following reactions?

g.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

a.

b.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

c.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

d.

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

e.

Identify A–E.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Starting with (R)-1-deuterio-1-propanol, how could you prepare

a. (S)-1-deuterio-1-propanol? 

Starting with (R)-1-deuterio-1-propanol, how could you prepare

b. (S)-1-deuterio-1-methoxypropane?

Starting with (R)-1-deuterio-1-propanol, how could you prepare

c. (R)-1-deuterio-1-methoxypropane?

When heated with H₂SO4, both 3,3-dimethyl-2-butanol and 2,3-dimethyl-2-butanol are dehydrated to form 2,3-dimethyl-2-butene. Which alcohol dehydrates more rapidly?

What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?

a. 0.1MHCl 

b. CH₃OH/HCl

What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?

c. 0.1MNaOH

What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?

d. CH₃OH/CH₃O^-

Write the appropriate reagent over each arrow.

Write the appropriate reagent over each arrow.

Write the appropriate reagent over each arrow.

Write the appropriate reagent over each arrow.

Write the appropriate reagent over each arrow.

Write the appropriate reagent over each arrow.

What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1-hexanol?

What is the major product(s) of each of the following reactions?

a.

b.

What is the major product(s) of each of the following reactions?

c.

What is the major product(s) of each of the following reactions?

d.

What is the major product(s) of each of the following reactions?

g.