Deck 9: Further Reactions of Alcohols and the Chemistry of Ethers

Question 1

What would be the product of the following reaction?

A)

B)

C)

D)

E)

Answer 1

Question 2

What would be the major organic product from the following reaction?

A)

B)

C)

D)

E)

Answer 2

Question 3

What reagent would best accomplish the following reaction?

A) Br₂
B) NaBr
C) CH₃Br
D) NH₄⁺ Br^-
E) PBr₃

Answer 3

PBr₃

Question 4

Which of the following reactions would be best for the preparation of Nerolin II?

A)

B)

C)

D) Any of the above would work.
E) None of the above would work.

Question 5

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 6

In the following reaction,an interesting rearrangement takes place.Suggest a structure for the product that is obtained.

A)

B)

C)

D)

E)

Question 7

What would be the product of the following reaction?

A)

B)

C)

D)

E)

Question 8

What would be the product of the following reaction?

A)

B)

C)

D)

E)

Question 9

What would be the best name of the following compound?

A) 3-methyl-4-oxohexane
B) 2-butoxyethane
C) 1-methy-1-ethoxypropane
D) (1-ethyl)-diethylether
E) 2-ethoxybutane

Question 10

Which of the following reactions would be the best for the preparation of anisole (methoxybenzene)?

A)

B)

C)

D)

E) None of the above would work.

Question 11

What would be the product of the following reaction?

A) CO₂ + H₂O
B)

C)

D)

E)

Question 12

What would be the expected product of the following reaction?

A)

B)

C)

D)

E)

Question 13

What product would result from the following reaction?

A)

B)

C)

D)

E)

Question 14

What is the product of the following reaction?

A)

B)

C)

D)

E)

Question 15

When considering the mechanism of the following reaction,which of the following statements is true?

A) A molecule of water is lost.
B) The mechanism involves an S_N2 reaction.
C) A free carbocation is formed.
D) An alkoxide is involved as a nucleophile.
E) Both A and C are true.

Question 16

What would be the expected product(s)of the following reaction?

A) CH₃CH₂CH₂CH₂OH + CH₃CH₂CH₂CH₂I
B) CH₃CH₂CH₂CHI-O-CH₂CH₂CH₂CH₃
C) 2 CH₃CH₂CH₂CH₂I
D)

E) no reaction occurs

Question 17

Which of the following would you expect to have the lowest boiling point?

A) CH₃CH₂OH
B) CH₃CH₂SH
C) CH₃OCH₃
D) CH₃SCH₃
E) The boiling points would be the same.

Question 18

What significant characteristic(s)does diethyl ether exhibit?

A) It functions as an anesthetic.
B) It is extremely flammable.
C) It is a common solvent.
D) It can react slowly with oxygen at room temperature.
E) All of the above are true.

Question 19

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 20

Ethers have lower boiling points than comparable alcohols because:

A) they are able to complex with the metal,magnesium.
B) they do not contain a carbonyl group.
C) the oxygen of the ether is sp² hybridized.
D) they are not able to hydrogen bond with themselves.
E) they have more acidic protons than alcohols.

Question 21

Which of the following reactions would produce diethyl ether?

A)

B)

C)

D) All of the above.
E) Two of the above.

Question 22

The Merck Index reports that the odor of geosmin can be detected at 0.1 parts per billion,but that it is quickly converted to essentially odorless products in acidic solution.What is the expected major product of treatment of geosmin with sulfuric acid?

A)

B)

C)

D)

E)

Question 23

Which set of reagents will effect the following transformation?

A) benzoic acid / H₃O⁺
B)

C) MCPBA
D) butanoic acid / H₃O⁺
E) CH₃CH₂OH / H₃O⁺

Question 24

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 25

Predict the major product of the following reaction

A)

B)

C)

D) A and B in equal proportions
E) B and C in equal proportions

Question 26

What is the major product of the following reaction:

A)

B)

C)

D)

E) None of the above.

Question 27

What is the major product of the following reaction:

A)

B)

C)

D)

E)

Question 28

Crown ethers are important because they

A) have antibiotic properties.
B) have the ability to dissolve certain salts in organic solvents.
C) occur in marine organisms.
D) promote the oxidation of certain organics.
E) are used as binders in detergent formulations.

Question 29

Give the IUPAC name for the following compound:

A) 1-ethoxy-2-methoxycyclobutane
B) 1-ethoxy-2-methoxycyclopropane
C) 1-methoxy-2-ethoxycyclobutane
D) 1-methoxy-2-ethoxycyclopropane
E) 1-methoxy-2-ethoxybutane

Question 30

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 31

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 32

Which type of inorganic esters tends to be shock-sensitive (explosive)?

A) Phosphate
B) Nitrate
C) Phosphite
D) Sulfate
E) Tosylate

Question 33

What type of reaction will happen to phenol upon treatment with catalytic sulfuric acid?

A) E1
B) E2
C) Free-radical elimination
D) Electrophilic elimination
E) A reaction will not take place.

Question 34

What is the structure of THF?

A)

B)

C)

D)

E)

Question 35

Diethyl ether can be dangerous for which of the following reasons:

A) It is highly toxic.
B) It tends to slowly accumulate hydroperoxides.
C) It is extremely flammable.
D) All of the above.
E) Two of the above.

Question 36

Which of the following is true of thiols?

A) They are more acidic than alcohols.
B) They have lower boiling points than the corresponding alcohol.
C) Thiol oxidations proceed very differently than alcohol oxidations.
D) All of the above.
E) Two of the above.

Question 37

Predict the major product of the following reaction: 2,3-dimethylcyclohexanol + H₂SO₄

A)

B)

C)

D)

E)

Question 38

Predict the major product of the following reaction:

A)

B)

C)

D)

E)

Question 39

Predict the major product of the following reaction:

A)

B)

C)

D)

E)

Question 40

Which of the following is a reasonable method of synthesizing methoxide?

A) CH₃OH + LDA
B) CH₃OH + nBuLi
C) CH₃OH + KH
D) Two of these are reasonable methods.
E) All of these would work.

Question 41

Which of the sequences below would accomplish the following transformation?

A)

B)

C)

D)

E)

Question 42

Predict the major product if the following reaction went by the S_N1 pathway:

A)

B)

C)

D)

E)

Question 43

For the transformations below,what is the structure of the product?

A)

B)

C)

D)

E) None of the above.

Question 44

For the transformations below,what is the structure of the starting material?

A) CH₃CH₂OH
B)

C)

D)

E) None of the above.

Question 45

For the transformations below,what is the structure of the major product?

A)

B)

C)

D)

E)

Question 46

For the transformations below,what is the structure of the starting material?

A)

B) CH₃CH₂OH
C)

D)

E)