Deck 14: Ethers and Epoxides; Thiols and Sulfides

Question 1

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

A) Diisobutylether
B) isobutyl isopropyl ether
C) sec-butyl isopropyl ether
D) Diisopropylether
E) none of these

Answer 1

isobutyl isopropyl ether

Question 2

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

Answer 2

Question 3

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

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

Answer 3

CH₃CH₂CH₂CH₂OH

Question 4

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

Question 5

What is the IUPAC name for the following compound?

Question 6

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 7

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

Question 8

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 9

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

Question 10

What is the IUPAC name for the following compound?

Question 11

What is the common name for CH₃CH₂CH₂OCH₂CH₂CH₃?

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

Question 12

Draw all constitutional isomers with molecular formula C₄H₈O having an ether functional group and provide the IUPAC name for each isomer.

Question 13

What is the correct structure for dibenzyl ether?

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

Question 14

What is the IUPAC name for the following compound?

Question 15

What is the correct structure for benzyl phenyl ether?

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

Question 16

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

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

What is the IUPAC name for the following compound?

Question 19

Provide an IUPAC name for the following compound.

Question 20

What is the IUPAC name for the following compound?

Question 21

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 22

Predict the product for the following reaction.

A) Propene
B) Diethyl ether
C) 1-hexanol
D) 1-propoxypropane

Question 23

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

Question 24

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 $\degree$ C
C) t-butyl bromide + bromomethane in presence of NaOH
D) sodium t-butoxide + bromomethane

Question 25

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 26

Which one of the following compounds has highest boiling point?

Question 27

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 28

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

Question 29

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

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

Question 30

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 31

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 32

Predict the product for the following reaction.

Question 33

What is the IUPAC name for the following compound?

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

Question 34

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

A) CH₃CH₂CH₂CH₂CH₃
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH₂CH₂OCH₃
D) CH₃CH₂CH₂Cl
E) CH₃CH₂OCH₂CHOH

Question 35

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

Question 36

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 37

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

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

Question 38

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

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

Question 39

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 40

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

Question 41

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

Question 42

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

Question 43

Predict the product for the following reaction.

Question 44

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Provide the reagents necessary to carry out the following conversion.

Question 45

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 46

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 47

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

Question 48

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

Question 49

Predict the product for the following reaction.

Question 50

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Predict the product for the following reaction.

Question 51

Predict the product for the following reaction.

Question 52

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

Question 53

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 54

Provide the reagents necessary to carry out the following conversion.

Question 55

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 56

Predict the product for the following reaction.

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

Question 57

Predict the product(s) for the following reaction.

Question 58

Predict the product(s) for the following reaction.

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

Question 59

Predict the product(s) for the following reaction.

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

Question 60

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 61

Predict the product for the following reaction. (E)-2-pentene + mCPBA

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

Question 62

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 63

Predict the product(s) for the following reaction.

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 IUPAC name for the following compound.

Question 66

Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane.

Question 67

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 68

Predict the product(s) for the following reaction.

Question 69

Provide the structure for oxetane.

Question 70

Provide the reagents necessary to carry out the following conversion.

Question 71

Predict the product for the following reaction. (Z)-3-hexene + mCPBA

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

Question 72

Predict the product for the following reaction.
1-methylcyclohexene + mCPBA $\rightarrow$

Question 73

Provide the IUPAC name for the following compound.

Question 74

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

Question 75

Predict the product for the following reaction.

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

Question 76

Provide the common name for the following compound.

Question 77

Provide the IUPAC name for the following compound.

Question 78

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

Question 79

Predict the product for the following reaction.

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

Question 80

Provide the structure for tetrahydrofuran.