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Bruice 8th EditionCh.10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 50c,d
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
c.
d.
Problem 51
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.)
Problem 52
Why is melphalan a good cancer drug?
Problem 55a
What is the product of each of the following reactions?
a.
Problem 55c,d
What is the product of each of the following reactions?
c.
d.
Problem 55g
What is the product of each of the following reactions?
g.
Problem 56a,b
Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H2SO4.
a.
b.
Problem 56c
Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H2SO4.
c.
Problem 56d
Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H2SO4.
d.
Problem 56e
Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H2SO4.
e.
Problem 57
Identify A–E.
Problem 57a(9)
a. Show the reagents required to form the primary alcohol in each of the following reactions.
Problem 58a
Starting with (R)-1-deuterio-1-propanol, how could you prepare
a. (S)-1-deuterio-1-propanol?
Problem 58b
Starting with (R)-1-deuterio-1-propanol, how could you prepare
b. (S)-1-deuterio-1-methoxypropane?
Problem 58c
Starting with (R)-1-deuterio-1-propanol, how could you prepare
c. (R)-1-deuterio-1-methoxypropane?
Problem 59a
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?
Problem 60a,b
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
a. 0.1MHCl
b. CH3OH/HCl
Problem 60c
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
c. 0.1MNaOH
Problem 60d
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
d. CH3OH/CH3O-
Problem 61a
Write the appropriate reagent over each arrow.
Problem 61b
Write the appropriate reagent over each arrow.
Problem 61c
Write the appropriate reagent over each arrow.
Problem 61d
Write the appropriate reagent over each arrow.
Problem 61e
Write the appropriate reagent over each arrow.
Problem 61f
Write the appropriate reagent over each arrow.
Problem 62
What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1-hexanol?
Problem 63a,b
What is the major product(s) of each of the following reactions?
a.
b.
Problem 63c
What is the major product(s) of each of the following reactions?
c.
Problem 63d
What is the major product(s) of each of the following reactions?
d.
Problem 63g
What is the major product(s) of each of the following reactions?
g.
