Question 1

Which of the following statements best explains why epoxides are more reactive than other ethers?

Accepted Answer

Epoxides have a three-membered ring that introduces significant angle strain, making the C—O—C bond angle $$60^{\circ}$$ instead of the tetrahedral $$109.5^{\circ}.$$

Question 2

Which of the following alcohols would dehydrate most rapidly under acidic conditions?

Accepted Answer

3$$^{\circ}$$ alcohol

Question 3

When naming an alcohol using IUPAC rules, which step ensures the correct placement of the OH group in the name?

Accepted Answer

Number the carbon chain to give the OH group the lowest possible number.

Question 4

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

$$\mathrm{HOCH_2CH_2CH_2CH_2OH}$$

Accepted Answer

1,4-butanediol

Question 5

Which of the following statements about hydrogen bonding in alcohols is TRUE?

Accepted Answer

Alcohols can form intermolecular hydrogen bonds due to the presence of an O—H bond.

Question 6

Which reagent is commonly used to convert a primary alcohol to an alkyl chloride via an $$S_N2$$ mechanism?

Accepted Answer

Thionyl chloride ($$\mathrm{$$SOCl_2$$}) in $$the presence of pyridine

Question 7

In the Williamson ether synthesis, which combination of reactants is preferred for the synthesis of unsymmetrical ethers?

Accepted Answer

An alkoxide ion attacking a less hindered (primary) alkyl halide

Question 8

Which of the following best describes the regioselectivity of epoxide ring opening under acidic conditions?

Accepted Answer

The nucleophile attacks the more substituted carbon atom of the epoxide.

Question 9

Which of the following is a correct statement about the stereochemistry of $$S_N2$$ reactions involving tosylates?

Accepted Answer

The $$S_N2$$ reaction proceeds with inversion of configuration at the stereogenic center.

Question 10

Which of the following is a common method for preparing thiols?

Accepted Answer

By $$S_N2$$ reaction of alkyl halides with $$\mathrm{SH^-}$$

Question 11

Which of the following is TRUE regarding the physical properties of ethers compared to alcohols?

Accepted Answer

Ethers are less polar and have lower boiling points than alcohols of similar molecular weight because they cannot hydrogen bond.

Question 12

Which of the following is the correct IUPAC name for the ether $$\mathrm{CH_3OCH_2CH_3}$$?

Accepted Answer

Methoxyethane

Question 13

What is the major product when 2-methyl-2-butanol undergoes dehydration with $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-methyl-2-butene

Question 14

Which of the following statements about the reaction of alcohols with hydrogen halides ($$\mathrm{HX}) is $$correct?

Accepted Answer

Primary alcohols react by an $$S_N2$$ mechanism, while tertiary alcohols react by an $$S_N1$$ mechanism.

Question 15

Which of the following is a consequence of carbocation rearrangement during alcohol dehydration?

Accepted Answer

The major product may have the double bond in an unexpected location due to a 1,2-hydride or alkyl shift.

Question 16

Which of the following is TRUE about the opening of an epoxide ring by a strong nucleophile?

Accepted Answer

The nucleophile attacks the less substituted carbon atom via an $$S_N2$$ mechanism.

Question 17

Which of the following is a correct statement about the formation of alkyl tosylates from alcohols?

Accepted Answer

Formation of the tosylate occurs with retention of configuration at the stereogenic center.

Question 18

Which of the following is a common cyclic ether used as a solvent in organic chemistry?

Accepted Answer

Tetrahydrofuran (THF)

Question 19

Which of the following is TRUE regarding the health effects of epoxides formed from polyaromatic hydrocarbons?

Accepted Answer

Epoxides are highly reactive and can disrupt cell function by reacting with biological nucleophiles such as DNA, potentially causing cancer.

Alcohols, Ethers, and Epoxides: Structure, Nomenclature, Properties, and Reactions

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