Deck 8: Ethers and Epoxides

Question 1

The best Williamson synthesis of cyclohexyl methyl ether involves the following reaction:

A)
B)
C)
D)
E)

Answer 1

Question 2

The mechanism by which ethers are cleaved in concentrated HI is:

A) S_N1
B) S_N2
C) E1
D) E2
E) none of these

Answer 2

S_N2

Question 3

The synthesis of dipropyl ether can be accomplished using 1-propanol.What reactants and conditions are necessary for this to occur?

A) Na and 180°
B) PBr₃ and 140°
C) H₂SO₄ and 140°
D) Zn and H⁺
E) PCC and 180°

Answer 3

H₂SO₄ and 140°

Question 4

What is a correct name for CH₃CH₂OCH₂CH₂CH₃?

A) diethyl ether
B) dipropyl ether
C) 1-propoxyethane
D) 1-ethoxypropane
E) 3-oxypentane

Question 5

The products of the following are:

A)
B)
C)
D)
E)

Question 6

Which one of the following molecules has the highest boiling point?

A) 3-methoxy-1-propanol
B) 1,2-dimethoxyethane
C) 1,4-butanediol
D) 1,1-dimethoxyethane
E) 2-methoxy-1-propanol

Question 7

The best route to CH₃OC(CH₃)₃ is

A)
B)
C)
D)
E)

Question 8

What is the IUPAC name for the following molecule?

A) 2-bromo-4-ethyl-4-methoxypentane
B) 4-bromo-2-ethyl-2-methoxypentane
C) 2-bromo-4-methoxy-4-methylhexane
D) 2-bromo-3-methoxy-3-methylhexane
E) ethyl methyl propyl ether

Question 9

Which of the following molecules is correctly named diphenyl ether?

A)
B)
C)
D)
E)

Question 10

The formula for 1-ethoxybutane is

A)
B)
C)
D)
E)

Question 11

Which reaction will yield CH₃CH₂CH₂D?

A) CH₃CH₂CH₃ + D₂O
B)CH₃CH₂CH₂MgCl + D₂O
C)CH₃CH₂CH₂OLi + D₂O
D)CH₃CH₂CH₂OH + D₂O
E) more than one of these

Question 12

Which of the following molecules is named oxirane?

A)
B)
C)
D)
E)

Question 13

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

A) 18, 6
B) 6, 18
C) 24, 6
D) 6, 24
E) 12, 6

Question 14

When anisole (methyl phenyl ether) is treated with concentrated HBr, which of the following products are produced?

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

Question 15

Which of the following molecules is the correct structure for dibenzyl ether?

A)
B)
C)
D)
E)

Question 16

What is the correct IUPAC name for the following molecule?

A) 1,2-dimethyloxirane
B) trans-1,2-dimethyloxirane
C) 2-butene oxide
D) cis-1,2-dimethyloxirane
E) oxobutane

Question 17

Which of the following is a Grignard reagent?

A) CH₃MgCl
B) CH₃Li
C) (CH₃)₂ CuLi
D) CH₃Na
E) (CH₃)₂ Zn

Question 18

What alkene reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl ether?

A) ethylene
B) 2-methylpropene
C) 2-butene
D) propene
E) 1-butene

Question 19

What is the correct name for the following crown ether?

A) [8]crown-4
B) [12]crown-4
C) [4]crown-4
D) [15]crown-5
E) [18]crown-6

Question 20

What is a name for the following molecule?

A) 3-ethoxy-3-methylpropane
B) ethyl isobutyl ether
C) butyl ethyl ether
D) 2-ethoxybutane
E) 3-ethoxybutane

Question 21

The first step in the mechanism of acid catalyzed ring opening of oxirane is:

A) protonation of the oxygen in the oxirane.
B) anion attack of the carbon in the oxirane.
C) cation attack of the carbon in the oxirane.
D) formation of a stable carbocation.
E) none of the above.

Question 22

Adding Br₂ in H₂O will distinguish which of following pairs of compounds?

A) diisopropyl ether and hexane
B) ethyl phenyl ether and allyl phenyl ether
C) 1-butanol and methyl propyl ether
D) diethyl ether and ethanol
E) toluene and anisole

Question 23

What is the final product of the following sequence of reactions?

A)
B)
C)
D)
E)

Question 24

Which of the following ethers are unsymmetrical?

A) CH₃OCH₂CH₃
B) (CH₃)₂CHOCH₂CH(CH₃)₂
C) CH₃OCH₃
D) CH₂CH₃OCH₂CH₃
E) both A and B

Question 25

Which of the following molecules is classified as an organic peroxy acid?

A)
B)
C)
D)
E)

Question 26

Which of the following ethers will cleave the fastest with H₂O and H⁺?

A)
B)
C)
D)
E)

Question 27

A reaction that would give n-butyllithium is

A) CH₃CH₂CH₂CH₃ + Li
B) CH₃CH₂CH₂CH₂Br + 2 Li
C) CH₃CH₂CH₂CH₂Br + LiBr
D) CH₃CH₂CH₂CH₂OH + Li
E) CH₃CH₂CH₂CH₃ + CH₃Li

Question 28

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

A) 1,2-cyclopentanediol
B) 1,2-pentanediol
C) pentanol
D) cyclopentene oxide
E) dicyclopentyl ether

Question 29

The organic products of the reaction below are are:

A) ethanol and iodobenzene.
B) ethyl iodide and iodobenzene.
C) ethanol and phenol.
D) ethyl iodide and phenol.
E) ethylene oxide and phenol.

Question 30

What is the final product in the following reaction sequence?

A)
B)
C)
D)
E) none of these

Question 31

Which reagent will accomplish the following reaction?

A) NaOH
B) CH₃CO₃H
C) H₂O, H₂SO₄
D) (a) BH₃ (b) NaOH, H₂O₂
E) CH₃CO₂H

Question 32

Which of following ethers will cleave by an S_N1 mechanism?

A)
B)
C)
D)
E)

Question 33

Which of the following statements about ethylene oxide is false?

A) Adds HBr according to Markovnikov's rule.
B) Can act as a Lewis base.
C) Reacts with Grignard reagents to give primary alcohols.
D) Can be made from ethene, oxygen, and a catalyst.
E) Can be hydrated to ethylene glycol.

Question 34

The correct structure for peroxyacetic acid is:

A)
B)
C)
D)
E)