Deck 13: Ethers and Epoxides; Thiols and Sulfides

Question 1

What is the IUPAC name for the following compound?

Answer 1

3-isopropoxy-2-methyloctane

Question 2

Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.

Answer 2

Question 3

What is the IUPAC name for CH₃CH₂OCH₂CH₂CH₂CH₂OCH₂CH₃?

A) 1,4-ethoxyoctane
B) diethoxy butyl ether
C) 1,2-diethoxymethane
D) 1,2-diethoxyhexane
E) 1,4-diethoxybutane

Answer 3

1,4-diethoxybutane

Question 4

What is the IUPAC name for the following compound?

Question 5

What is the correct structure for benzyl phenyl ether?

A) I
B) II
C) III
D) IV
E) none of these

Question 6

What is the common name for (CH₃)₂CHCH₂OCH(CH₃)₂?

A) diisobutyl ether
B) isobutyl isopropyl ether
C) sec-butyl isopropyl ether
D) diisopropyl ether
E) none of these

Question 7

Draw all constitutional isomers with molecular formula C₆H₁₄O having an ether functional group and provide the IUPAC name for each isomer.

Question 8

What is the common name for the following compound?

A) 1-butoxybutane
B) sec-butyl isopropyl ether
C) sec-butyl t-butyl ether
D) n-butyl isopropyl ether
E) none of these

Question 9

Provide the structure for (2S,5R)-5-ethoxy-2-octanol.

Question 10

Provide an IUPAC name for the following compound.

Question 11

What is the IUPAC name for the following compound?

Question 12

What is the common name for CH₃CH₂CH₂OCH₂CH₂CH₃?

A) dibutyl ether
B) 1-propoxypropane
C) 1-propoxyhexane
D) dipropyl ether
E) none of these

Question 13

What is the IUPAC name for CH₃CH₂CH₂CH₂OCH₂CH₃?

A) 1-ethoxybutane
B) 1-butoxyethane
C) ethyl butyl ether
D) 1-ethoxyhexane
E) none of these

Question 14

Which one of the following compounds will have the highest boiling point?

A) CH₃CH₂CH₂CH₂CH₃
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH₂CH₂OCH₃
D) CH₃CH₂CH₂Cl
E) CH₃CH₂OCH₂CH₃

Question 15

Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene.

Question 16

What is the IUPAC name for the following compound?

Question 17

Which of the following compounds is(are) classified as ethers?

A) I
B) II & IV
C) III
D) I & III
E) all of these

Question 18

Draw all constitutional isomers with molecular formula C₄H₈O having an ether functional group.

Question 19

What is the correct structure for dibenzyl ether?

A) I
B) II
C) III
D) IV
E) none of these

Question 20

What is the IUPAC name for the following compound?

Question 21

Predict the product for the following reaction.

A) propene
B) diethyl ether
C) 1-hexanol
D) 1-propoxypropane

Question 22

Which of the following crown ether solvates sodium ions?

A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these

Question 23

Which one of the following compounds will have the highest boiling point?

A) CH₃CH₂CH₂CH₂CH₃
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH₂CH₂OCH₃
D) CH₃CH₂CH₂Cl
E) CH₃CH₂OCH₂CH₂OH

Question 24

Which one of the following compounds has highest boiling point?

A) I
B) II
C) III
D) IV
E) V

Question 25

Ethers with larger alkyl groups have higher boiling points due to ___________ .

A) dipole-dipole interactions
B) ion-dipole interactions
C) ion-ion interactions
D) London dispersion forces
E) hydrogen bonding

Question 26

Predict the product for the following reaction.

Question 27

What type of molecular interactions do ethers have?

A) dipole-dipole interactions
B) ion-dipole interactions
C) ion-ion interactions
D) London dispersion forces
E) hydrogen bonding

Question 28

Provide a curved arrow mechanism for the formation of the product shown.

Question 29

Identify the missing reagent needed to carry out the following reaction.

A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these

Question 30

Identify the missing reagent needed to carry out the following reaction.

A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these

Question 31

Identify a common ether solvent that was once used as an anesthetic.

A) diethyl ether
B) ethanol
C) methanol
D) isopropyl alcohol
E) dimethyl ether

Question 32

Which of the following crown ether solvates potassium ions?

A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these

Question 33

What is the correct IUPAC name for the following compound?

A) 12-crown-5
B) 12-crown-4
C) 4-crown-12
D) 12-crown-12
E) none of these

Question 34

Rank the following compounds in decreasing order of water solubility (highest to lowest).

A) II > IV > I > III
B) I > IV > II > III
C) IV > I > II > III
D) III > II > I > IV
E) IV > III > I > II

Question 35

Which one of the following compounds will be least soluble in water?

A) diethyl ether
B) methyl propyl ether
C) 1-butanol
D) 2-butanol
E) pentane

Question 36

Identify the missing reagent needed to carry out the following equation.

Question 37

Identify the missing reagent needed to carry out the following equation.

Question 38

Rank the following compounds in decreasing order of boiling points (highest to lowest).

A) II > IV > I > III
B) I > IV > II > III
C) IV > I > II > III
D) III > II > I > IV
E) IV > II > I > III

Question 39

Which of the following crown ether solvates lithium ions?

A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these

Question 40

The polyethers that function like crown ethers are called _________.

Question 41

Predict the product for the following reaction.

Question 42

Which one of the following reactions would produce t-butyl methyl ether in high yield?

A) CH₃ONa + (CH₃)₃CBr
B) CH₃OH + (CH₃)₃COH in the presence of H₂SO₄ at 140°C
C) CH₃Cl + (CH₃)₃CBr in the presence of NaOH
D) (CH₃)₃CONa + CH₃Br

Question 43

Provide the reagents necessary to carry out the following conversion.

Question 44

Predict the product for the following reaction.

A) 2-methyl-1-hexanol
B) 2-methoxy-2-methylhexane
C) 1-methoxy-2-methylhexane
D) 2-methoxy-3-methylhexane
E) 2-methyl-2-hexanol

Question 45

Predict the product for the following reaction.

Question 46

Predict the product for the following reaction.

A) 3-methyl-3-pentanol
B) 3-ethoxy-3-methylpentane
C) 3-methyl-2-pentanol
D) 2-ethoxy-3-methylpentane
E) 1-ethoxy-3-methylpentane

Question 47

Predict the product for the following reaction.

Question 48

Identify the mechanism for the Williamson ether synthesis.

A) SN1 mechanism
B) SN2 mechanism
C) E1 mechanism
D) E1 Mechanism

Question 49

Which one of the following reactions would produce (S)-3-methoxyheptane in high yield?

A) sodium (S)-3-heptoxide + bromomethane
B) sodium (R)-3-heptoxide + bromomethane
C) sodium methoxide + (S)-3-bromoheptane
D) sodium methoxide + (R)-3-bromoheptane

Question 50

Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 51

Provide the reagents necessary to prepare the following compound using alkoxymercuration-demercuration.

Question 52

Provide the reagents necessary to carry out the following reaction.

Question 53

Predict the product for the following reaction.

A) 1-ethylcyclohexanol
B) 2-ethoxy-1-ethylcyclohexane
C) 1-ethoxy-1-ethylcyclohexane
D) 2-ethoxy-3-ethylcyclohexane
E) 1-ethoxy-2-ethylcyclohexane

Question 54

Which one of the following reactions would produce t-butyl methyl ether in high yield?

A) t-butyl chloride + sodium methoxide
B) t-butanol + methanol in presence of H₂SO₄ at 140°C
C) t-butyl bromide + bromomethane in the presence of NaOH
D) sodium t-butoxide + bromomethane

Question 55

Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis.

Question 56

Predict the product for the following reaction.

Question 57

Predict the product(s) for the following reaction.

A) ethanol + 1-bromopropane
B) 1-propanol + bromoethane
C) 1-propanol + ethanol
D) 1-bromopropane + bromoethane
E) none of these

Question 58

Can you prepare diisopropyl ether as the major product by heating 2-propanol in the presence of sulfuric acid? Explain your answer.

Question 59

Identify the conditions of oxymercuration-demercuration.

A) anti-Markovnikov, rearrangement possible
B) anti-Markovnikov, no rearrangement possible
C) Markovnikov, rearrangement possible
D) Markovnikov, no rearrangement possible

Question 60

Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis reaction.

Question 61

Predict the product(s) for the following reaction.

Question 62

Explain why long-term storage of ethers can be dangerous.

Question 63

What is the IUPAC name for the following compound?

A) 2-ethyl-3-isopropyl-2-methyloxirane
B) 1-ethyl-2-isopropyl-1-methyloxirane
C) 2,4-dimethyloxyhexane
D) 1-ethyl-2,4-dimethyloxyhexane
E) 3-ethyl-2-isopropyl-3-methyloxirane

Question 64

Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 65

Provide the structure for oxetane.

Question 66

Predict the product(s) for the following reaction.

A) ethanol + phenol
B) phenol + iodoethane
C) iodobenzene + ethanol
D) iodobenzene + iodoethane
E) none of these

Question 67

Provide the structure for oxolane.

Question 68

What is the IUPAC name for the following compound?

A) 3-ethyl-2-methyloxirane
B) 2-ethyl-3-methyloxirane
C) 2-ethyl-1-methyloxypentane
D) 1-ethyl-2-methyloxypentane
E) none of these

Question 69

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 70

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 71

Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 72

Provide the IUPAC name for the following compound.

Question 73

Provide the structure for tetrahydrofuran.

Question 74

Provide the IUPAC name for the following compound.

Question 75

Provide the structure for oxane.

Question 76

Predict the product(s) for the following reaction.

Question 77

Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane.

Question 78

Provide the common name for the following compound.

Question 79

Provide the IUPAC name for the following compound.

Question 80

Predict the product(s) for the following reaction.