Question 1

Which of the following statements best explains why ethers have lower boiling points than alcohols of comparable molecular weight?

Accepted Answer

Ethers cannot form hydrogen bonds with each other because they lack an O-H group.

Question 2

Arrange the following compounds in order of increasing solubility in water: hexane, diethyl ether, ethylene glycol dimethyl ether.

Accepted Answer

Hexane \u003c Diethyl ether \u003c Ethylene glycol dimethyl ether

Question 3

Which of the following combinations would give the highest yield of an ether via the Williamson ether synthesis?

Accepted Answer

$$\mathrm{CH_3CH_2ONa}$$ + $$\mathrm{CH_3Br}$$

Question 4

What is the major organic product when 2-bromo-2-methylpropane reacts with sodium methoxide?

Accepted Answer

2-Methylpropene

Question 5

Which of the following best describes the mechanism for the acid-catalyzed dehydration of ethanol to form diethyl ether?

Accepted Answer

Protonation of ethanol, nucleophilic attack by another ethanol, loss of water, and deprotonation

Question 6

Which of the following is the correct IUPAC name for the compound shown below?

$$\mathrm{CH_3CH_2SCH_2CH_3}$$

Accepted Answer

Ethylsulfanylethane

Question 7

Which reagent is commonly used for the laboratory synthesis of epoxides from alkenes?

Accepted Answer

A peroxycarboxylic acid such as mCPBA

Question 8

What is the stereochemical outcome when cis-2-butene is treated with a peroxycarboxylic acid?

Accepted Answer

A single meso epoxide is formed

Question 9

Which of the following best describes the regioselectivity of acid-catalyzed ring opening of an unsymmetrical epoxide?

Accepted Answer

Nucleophilic attack occurs at the more substituted carbon

Question 10

Which product is formed when oxirane (ethylene oxide) is treated with water in the presence of acid?

Accepted Answer

$$\mathrm{HOCH_2CH_2OH} ($$ethylene glycol)

Question 11

Which of the following is a correct statement about the oxidation of sulfides?

Accepted Answer

Treatment of a sulfide with one equivalent of $$\mathrm{H_2O_2}$$ gives a sulfoxide.

Question 12

Which of the following best explains why the acid-catalyzed dehydration of a mixture of ethanol and 1-hexanol gives a low yield of ethyl hexyl ether?

Accepted Answer

Multiple ethers are formed due to the presence of two different alcohols.

Question 13

Which of the following is the correct mechanism for the conversion of a halohydrin to an epoxide?

Accepted Answer

Internal SN2 displacement of the halide by the alkoxide

Question 14

What is the major product when 1,2-epoxycyclopentane is treated with aqueous acid?

Accepted Answer

trans-1,2-Cyclopentanediol (a racemic mixture)

Question 15

Which of the following best describes the difference in the products formed by acid-catalyzed hydrolysis of an epoxide and oxidation of an alkene with osmium tetroxide?

Accepted Answer

Epoxide hydrolysis gives anti diols, while osmium tetroxide oxidation gives syn diols.

Question 16

Which of the following is the correct IUPAC name for the compound $$\mathrm{CH_3CH_2SSCH_2CH_3}$$?

Accepted Answer

Ethyl disulfanylethane

Question 17

Which of the following best describes the product of the reaction of cyclohexene with peroxyacetic acid?

Accepted Answer

1,2-Epoxycyclohexane (Cyclohexene oxide)

Question 18

Which of the following is a key feature of the mechanism for alkene epoxidation with peroxycarboxylic acids?

Accepted Answer

The reaction is stereospecific with retention of alkene configuration.

Question 19

Which of the following is the correct product when methyl phenyl sulfide is treated with one equivalent of $$\mathrm{H_2O_2}$$?

Accepted Answer

Methyl phenyl sulfoxide

Ethers, Epoxides, and Sulfides: Structure, Properties, Synthesis, and Reactions

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