Deck 11: Ethers, Epoxides, and Sulfides

Question 1

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Answer 1

2

Question 2

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Answer 2

3

Question 3

What is the IUPAC name of the following compound?

A) ethyl isopropyl thiol
B) 2-ethylsulfanylpropane
C) ethyl isopropyl disulfide
D) isopropylsufanylethane

Answer 3

2-ethylsulfanylpropane

Question 4

Which of the following are epoxides?

A) only 2 and 3
B) only 3 and 4
C) only 2, 3 and 4
D) 1, 2, 3 and 4

Question 5

What type of mechanism accounts for the cleavage of tert-butyl methyl ether upon treatment with HBr?

A) S_N1
B) S_N2
C) E1
D) E2

Question 6

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 7

What type of mechanism accounts for the cleavage of dibutyl ether upon treatment with HBr to give two moles of 1-bromobutane?

A) S_N1
B) S_N2
C) E1
D) E2

Question 8

What is the IUPAC name of the following compound?

A) cis-1,4-anisole
B) cis-4-methoxyanisole
C) cis-1,4-dimethoxycyclohexane
D) para-dianisole

Question 9

Which of the following are ethers?

A) only 1 and 2
B) only 1 and 4
C) only 1, 2 and 3
D) 1, 2, 3 and 4

Question 10

Which of the following statements are true?
1.ethanol is more soluble in water than dimethyl ether
2.ethanol has a higher boiling point than dimethyl ether
3.ethanol has the same molecular weight as dimethyl ether

A) only 1
B) only 1 and 2
C) only 1 and 3
D) 1, 2 and 3

Question 11

What is the correct assignment of the names of the following ethers?

A) 1 = oxirane; 2 = oxetane; 3= oxolane
B) 1 = oxetane; 2 = oxirane; 3= oxane
C) 1 = oxane; 2 = oxetane; 3= dioxane
D) 1 = oxirane; 2 = oxolane; 3= oxetane

Question 12

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 13

What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide?

A) tert-butyl anion
B) tert-butoxide
C) tert-butyl radical
D) tert-butyl cation

Question 14

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

A) tert-butyl phenyl ether
B) isopropyl methyl ether
C) anisole
D) tert-butyl methyl ether

Question 15

What is the correct assignment of the names of the following ethers?

A) 1 = oxirane; 2 = oxetane; 3 = oxane
B) 1 = oxirane; 2 = oxitane; 3 = oxane
C) 1 = oxane; 2 = dioxane; 3 = oxetane
D) 1 = oxirane; 2 = oxolane; 3 = oxane

Question 16

Which of the following reactions provides tert-butyl methyl ether in a high yield?

A) potassium tert-butoxide + iodomethane
B) sodium methoxide + tert-butyl bromide
C) methanol + tert-butyl alcohol in the presence of KOH
D) iodomethane + tert-butyl bromide in the presence of KOH

Question 17

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 18

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 19

Which of the following reactions provides anisole (PhOCH₃) in a high yield?

A) phenol + sodium methoxide
B) bromobenzene + bromomethane
C) sodium phenoxide (PhONa) + bromomethane
D) bromobenzene + sodium methoxide

Question 20

Which of the following are thiols?

A) only 1
B) only 1 and 4
C) only 2 and 3
D) 1, 2, 3 and 4

Question 21

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 22

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 23

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 24

What are the major products obtained upon treatment of tert-butyl methyl ether with excess HBr?

A) tert-butyl alcohol and methanol
B) tert-butyl bromide and methanol
C) tert-butyl alcohol and bromomethane
D) tert-butyl bromide and bromomethane

Question 25

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 26

What are the major products obtained upon treatment of anisole, PhOCH₃, with excess HBr?

A) phenol and methanol
B) bromobenzene and bromomethane
C) phenol and bromomethane
D) bromobenzene and methanol

Question 27

What is the major organic product obtained from the following reaction?

A) only 1
B) only 2
C) only 3
D) both 2 and 3

Question 28

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 29

What is the best choice of reagent(s) to perform the following transformation?

A) CH₃MgBr; followed by H₃O⁺
B) H₂O, NaOH
C) LiAlH₄ followed by H₃O⁺
D) KMnO4

Question 30

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 31

What is the best choice of reagent(s) to perform the following transformation?

A) H₂O
B) H₂SO₄, H₂O
C) LiAlH₄ followed by H₃O⁺
D) KMnO4

Question 32

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 33

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 34

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 35

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 36

What is the best choice of reagent(s) to perform the following transformation?

A) O₃
B) peroxyacid
C) OsO₄; followed by NaHSO₃
D) H₂O, H₂SO₄

Question 37

What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)?

A) tert-butyl cation
B) tert-butyl radical
C) tert-butyl anion
D) tert-butoxide

Question 38

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 39

What is the major organic product obtained from the following reaction?

A) only 1
B) only 2
C) only 3
D) both 2 and 3

Question 40

What is the best choice of reagent(s) to perform the following transformation?

A) peroxyacid
B) Br₂, H₂O; followed by NaOH, H₂O
C) OsO₄; followed by NaHSO₃
D) H₂O, H₂SO₄

Question 41

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 42

What is the name of the following compound?

A) 6-crown-12
B) 12-crown-6
C) 18-crown-12
D) 18-crown-6

Question 43

What would be the best choice of reagent(s) to perform the following transformation?

A) CH₃OH, H₂SO₄
B) NaOEt, followed by CH₃OH
C) NaOEt, followed by CH₃I
D) CH₃OCH₃

Question 44

Which of the following synthetic routes is used in industry to provide epichlorohydrin?

A) 1
B) 2
C) 3
D) 4

Question 45

Which of the following ions forms the strongest complex with 18-crown-6?

A) Li⁺
B) Na⁺
C) K⁺
D) Rb⁺

Question 46

What would be the best choice of reagent(s) to perform the following transformation?

A) H₃O⁺
B) H₂O, NaOH
C) LiAlH₄ followed by H₃O⁺
D) H₂O₂

Question 47

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 48

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 49

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 50

What would be the best choice of reagent(s) to perform the following transformation?

A) CH₃S^-Na⁺
B) CH₃SH, H₂SO₄
C) CH₃OH, Na₂S
D) CH₃I, H₂SO₄

Question 51

What is the IUPAC name of the following compound?

Question 52

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 53

Which of the following general structures can be made by sequential reaction of epichlorohydrin with appropriate nucleophiles?

A) 1
B) 2
C) 3
D) 4

Question 54

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 55

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 56

Which of the following statements is not true?

A) Crown ethers complex alkali metal ions by donation of lone pairs from the oxygen atoms to the metal cation.
B) Metal ion complexes of crown ethers dissolve in nonpolar aprotic organic solvents
C) Addition of 18-crown-6 to a solution of benzyl bromide and potassium cyanide in a nonpolar solvent increases the rate of nucleophilic substitution.
D) 18-Crown-6 is a planar molecule

Question 57

What is the major organic product obtained from the following sequence of reactions?

A) 1
B) 2
C) 3
D) 4

Question 58

What would be the best choice of reagent(s) to perform the following transformation?

A) H₂O₂
B) NaIO₄
C) H₂O, NaOH
D) H₂SO₄

Question 59

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 60

What is the IUPAC name of the following compound?

Question 61

What is the IUPAC name of the following compound?

Question 62

What is the IUPAC name of the following compound?

Question 63

What is the major organic product obtained from the following reaction?

Question 64

What is the major organic product obtained from the following reaction?

Question 65

What is the major organic product obtained from the following reaction?

Question 66

What is the major organic product obtained from the following reaction?

Question 67

Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

Question 68

What is the major organic product obtained from the following reaction?

Question 69

Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

Question 70

What is the major organic product obtained from the following reaction?

Question 71

What is the major organic product obtained from the following reaction?