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 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

Answer 2

1 = oxirane; 2 = oxolane; 3 = oxane

Question 3

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

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

Answer 3

2

Question 4

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

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

Question 5

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 6

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 7

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 8

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

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

Question 9

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 10

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 11

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 12

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 13

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 14

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 15

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 16

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

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

Question 17

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 18

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 19

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

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

Question 20

What is the IUPAC name of the following compound?

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

Question 21

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

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

Question 22

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

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 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 25

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

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

Question 26

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

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

Question 27

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

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

Question 28

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

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

Question 29

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 30

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

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

Question 31

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 32

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 33

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 34

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

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 major organic product obtained from the following sequence of reactions?

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

Question 37

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 38

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 39

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 40

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 41

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

A)Li⁺
B)Na⁺
C)K⁺
D)Rb⁺

Question 42

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 43

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

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

Question 44

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

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

Question 45

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

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

Question 46

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 47

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 48

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

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

Question 49

The correct structure for dibenzyl ether is shown below.

Question 50

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

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

Question 51

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

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

Question 52

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 53

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

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

Question 54

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

A)CH₃^-Na⁺
B)CH₃SH, H₂SO₄
C)CH₃OH, Na₂S
D)CH₃I, H₂SO₄

Question 55

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

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

Question 56

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

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

Question 57

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

A)H₂O₂
B)NaIO₄
C)H₂O, NaOH
D)H₂SO₄

Question 58

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

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

Question 59

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 60

The structure shown below can be named as either ethylene oxide or oxirane.

Question 61

The following reaction would result in the formation of a ____________group.

Question 62

The first step in the mechanism of acid catalyzed ring opening of oxirane is protonation of the oxygen in the oxirane.

Question 63

Consider the cleavage of the following ether with H₂O and H⁺. Cleavage of the following ether will be a slower process.

Question 64

The correct name for the following compound is 12-crown-4.

Question 65

The correct name for the following compound is cyclopropyl ethyl thiol.

Question 66

The following reaction is a valid means of preparing the given product.

Question 67

Consider the following reaction. The name of the aromatic product is __________________.

Question 68

Consider the following reaction. The major organic product obtained from the reaction is

Question 69

The following reaction would be best accomplished by the addition of _______________. (Assume that CH₃CO₂H is also produced.)

Question 70

The correct name for the following substance is cis-1,2-dimethyloxirane.

Question 71

A protecting group changes the reactivity of a functional group to one that is inert to reaction conditions without becoming a permanent part of the molecule.

Question 72

Consider the reaction below to answer the following questions.
The reaction shown here is an example of a ______________ ________synthesis

Question 73

The name of the alkene that reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl ether is ________________.

Question 74

Adding Br₂ in H₂O will distinguish between ethyl phenyl ether and allyl phenyl ether.

Question 75

Consider the reaction below to answer the following questions.
The reaction shown here proceeds by a(n) _______ mechanism.

Question 76

Consider the reaction below to answer the following questions.
The name of the product of the reaction is _______________________.

Question 77

When cyclopentene is treated with peroxyacetic acid, the product that forms is _________________.

Question 78

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

Question 79

The first step in the following conversion should be the addition of (CH₃)₃SiCl, (CH₃CH₂)₃N.

Question 80

The synthesis of dipropyl ether can be accomplished by reacting 1-propanol with H₂SO₄ at 140°C.