University of New England

CHEM 1020

Chapter 8 -- Ethers and Epoxides

MULTIPLE CHOICE

1)What is a correct name for CH₃CH₂OCH₂CH₂CH₃?

1. 1. diethyl ether
   2. dipropyl ether
   3. 1-propoxyethane
   4. 1-ethoxypropane
   5. 3-oxypentane

2. Which of the following molecules is the correct structure for dibenzyl ether?

A)

B)

C)

D)

E)

3. What is the IUPAC name for the following molecule?

1. 1. 2-bromo-4-ethyl-4-methoxypentane
   2. 4-bromo-2-ethyl-2-methoxypentane
   3. 2-bromo-4-methoxy-4-methylhexane
   4. 2-bromo-3-methoxy-3-methylhexane
   5. ethyl methyl propyl ether

4. Which of the following molecules is named oxirane?

A)

B)

C)

D)

E)

5. 
   What is the correct IUPAC name for the following molecule?

1. 1. 1,2-dimethyloxirane
   2. trans-1,2-dimethyloxirane
   3. 2-butene oxide
   4. cis-1,2-dimethyloxirane
   5. oxobutane

6. Which of the following molecules is correctly named diphenyl ether?

A)    

B)

C)

D)

E)

7. What is a name for the following molecule?

1. 1. 3-ethoxy-3-methylpropane
   2. ethyl isobutyl ether
   3. butyl ethyl ether
   4. 2-ethoxybutane
   5. 3-ethoxybutane

8. What is the correct name for the following crown ether?

1. 1. [8]crown-4
   2. [12]crown-4
   3. [4]crown-4
   4. [15]crown-5
   5. [18]crown-6

9. A crown ether named [18]crown-6 has a total of              carbons and              oxygens .

A) 18, 6

B) 6, 18

C) 24, 6

D) 6, 24

E)   12, 6

10. The formula for 1-ethoxybutane is

A)

C)

E)

11. Which one of the following molecules has the highest boiling point?
    1. 3-methoxy-1-propanol
    2. 1,2-dimethoxyethane
    3. 1,4-butanediol
    4. 1,1-dimethoxyethane
    5. 2-methoxy-1-propanol

12. Which of the following is a Grignard reagent?
    1. CH₃MgCl
    2. CH₃Li
    3. (CH₃)₂ CuLi
    4. CH₃Na
    5. (CH₃)₂ Zn

13. Which reaction will yield CH₃CH₂CH₂D?
    1. CH₃CH₂CH₃ + D₂O
    2. CH₃CH₂CH₂MgCl + D₂O
    3. CH₃CH₂CH₂OLi + D₂O
    4. CH₃CH₂CH₂OH + D₂O
    5. more than one of these

14. Starting with p-bromoanisole (p-bromophenyl methyl ether), what sequence of reactions will produce p-deuterioanisole?

1. 1. 1. D₂O 2. Br₂, AlBr₃
   2. 1. Mg, ether 2. D₂O
   3. 1. D₂O 2. Mg, ether
   4. 1. H₂SO₄, D 2. Mg, ether 3. D₂O

1. 5. 1. Br₂, AlBr₃, 2. Mg, ether, 3. D₂O

15. 
    The products of the following are:

A)

B)

D)

16. The synthesis of dipropyl ether can be accomplished using 1-propanol. What reactants and conditions are necessary for this to occur?
    1. Na and 180°
    2. PBr₃ and 140°
    3. H₂SO₄ and 140°
    4. Zn and H⁺
    5. PCC and 180°

17. The best Williamson synthesis of cyclohexyl methyl ether involves the following reaction:

A)

B)

C)

D)

E)

18. What alkene reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl ether?
    1. ethylene
    2. 2-methylpropene
    3. 2-butene
    4. propene
    5. 1-butene

19. The best route to CH₃OC(CH₃)₃ is

A)

B)     

C)

D)

E)

20. When anisole (methyl phenyl ether) is treated with concentrated HBr, which of the following products are produced?

1. 1. I
   2. II
   3. III
   4. IV
   5. I and IV

21. The mechanism by which ethers are cleaved in concentrated HI is:
    1. S_N1
    2. S_N2
    3. E1
    4. E2
    5. none of these

22. Which of the following ethers will cleave the fastest with H₂O and H⁺?

A)

B)

C)

D)

E)

23. Which of following ethers will cleave by an S_N1 mechanism?

A)

B)

C)

D)

E)

24. The organic products of the reaction below are

are:

1. 1. ethanol and iodobenzene.
   2. ethyl iodide and iodobenzene.
   3. ethanol and phenol.
   4. ethyl iodide and phenol.
   5. ethylene oxide and phenol.

25. Which of the following molecules is classified as an organic peroxy acid?

B)

C)

D)

E)

26. The first step in the mechanism of acid catalyzed ring opening of oxirane is:
    1. protonation of the oxygen in the oxirane.
    2. anion attack of the carbon in the oxirane.
    3. cation attack of the carbon in the oxirane.
    4. formation of a stable carbocation.
    5. none of the above.

27. When cyclopentene is treated with peroxyacetic acid, the product that forms is:
    1. 1,2-cyclopentanediol
    2. 1,2-pentanediol
    3. pentanol
    4. cyclopentene oxide
    5. dicyclopentyl ether

28. The correct structure for peroxyacetic acid is:

A)

B)    

C)    

D)

E)    

29. What is the final product of the following sequence of reactions?

1. 1. 
      D)
   2. E)

30. Which of the following statements about ethylene oxide is false?
    1. Adds HBr according to Markovnikov's rule.
    2. Can act as a Lewis base.
    3. Reacts with Grignard reagents to give primary alcohols.
    4. Can be made from ethene, oxygen, and a catalyst.
    5. Can be hydrated to ethylene glycol.

31. 
    Which reagent will accomplish the following reaction?

1. 1. NaOH
   2. CH₃CO₃H
   3. H₂O, H₂SO₄
   4. (a) BH₃ (b) NaOH, H₂O₂
   5. CH₃CO₂H

32. 
    The product of the reaction below is

1. 1. CH₃CH₂CH₂CH₃.
   2. CH₃CH₂OCH₂CH₂OH.
   3. CH₃CH₂OCH₂CH₂OCH₂CH₃.
   4. CH₃CH₂OCH₂CH₂CH₂OH.
   5. none of the above.
   6. all of the above.

33. 1-Hexanol and 1-ethoxybutane are examples of:
    1. enantiomers
    2. diastereomers
    3. stereoisomers
    4. constitutional isomers
    5. none of these

34. What is the final product in the following reaction sequence?

A)

B)

C)

D)

E) none of these