Deck 14: Ethers and Epoxides; Thiols and Sulfides

Question 1

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

Answer 1

IV>I>II>III

Question 2

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

Answer 2

15-crown-5

Question 3

What is the IUPAC name for the following compound?

Answer 3

1,1,1-triethoxyethane

Question 4

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 5

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

Question 6

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

Question 7

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 8

What is the common name for CH₃CH₂CH₂OCH₂CH₂CH₃?

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

Question 9

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 10

What is the IUPAC name for the following compound?

Question 11

What is the IUPAC name for the following compound?

Question 12

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 13

What is the correct structure for benzyl phenyl ether?

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

Question 14

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 15

What is the correct structure for dibenzyl ether?

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

Question 16

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

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

Question 17

What is the IUPAC name for the following compound?

Question 18

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 19

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

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

Question 20

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

Question 21

Predict the product for the following reaction.

Question 22

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

Question 23

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 24

Predict the product for the following reaction.

Question 25

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

Question 26

Predict the product for the following reaction.

Question 27

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

Question 28

Predict the product(s)for the following reaction.

A)ethanol + phenol
B)phenol + 1-iodoethane
C)iodobenzene + ethanol
D)iodobenzene + 1-iodoethane
E)none of these

Question 29

Predict the product(s)for the following reaction.

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

Question 30

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 31

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

Question 32

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 33

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

Question 34

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 35

Predict the product for the following reaction.

Question 36

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

Question 37

Predict the product for the following reaction.

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

Question 38

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 39

Predict the product(s)for the following reaction.

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

Question 40

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 41

Provide the IUPAC name for the following compound.

Question 42

Provide the common name for the following compound.

Question 43

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

Question 44

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

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

Question 45

Provide the structure for tetrahydrofuran.

Question 46

What is the IUPAC name for the following compound?

A)2-ethyl-1-isopropyl-2-methyloxirane
B)1-ethyl-2-isopropyl-1-methyloxirane
C)2,4-dimethyloxyhexane
D)1-ethyl-2,4-dimethyloxyhexane
E)none of these

Question 47

Provide the IUPAC name for the following compound.

Question 48

Provide the IUPAC name for the following compound.

Question 49

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

Question 50

Predict the product(s)for the following reaction.

Question 51

Provide the structure for 1,1,2-trimethyl-2-phenyloxirane.

Question 52

Predict the product(s)for the following reaction.

Question 53

Predict the product for the following reaction.

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

Question 54

Provide the structure for oxetane.

Question 55

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

Question 56

Predict the product(s)for the following reaction.

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

Question 57

What is the IUPAC name for the following compound?

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

Question 58

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

Question 59

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

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

Question 60

Predict the product(s)for the following reaction.

Question 61

Predict the product(s)for the following reaction.

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

Question 62

Provide the reagents necessary to carry out the following conversion.

Question 63

Provide the structure(s)of the product(s)in the following reaction sequence.

Question 64

Provide the reagents necessary to carry out the following conversion.

Question 65

Predict the product(s)for the following reaction.

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

Question 66

Predict the product(s)for the following reaction.

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

Question 67

Predict the product(s)for the following reaction.

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

Question 68

Predict the product(s)for the following reaction.

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

Question 69

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

Question 70

Predict the product for the following reaction.

Question 71

Provide the reagents necessary to carry out the following conversion.

Question 72

Predict the product for the following reaction.

Question 73

Predict the product for the following reaction.

Question 74

Predict the product(s)for the following reaction.

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

Question 75

Predict the product(s)for the following reaction.

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

Question 76

Predict the product for the following reaction.

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

Question 77

Predict the product(s)for the following reaction.

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

Question 78

Predict the product for the following reaction.

Question 79

Predict the product for the following reaction.

Question 80

Predict the product for the following reaction.