Q: Which reagent(s) would you use to convert 1-butanol to butyl ethyl ether using the Williamson ether synthesis?

$$\mathrm{1. NaH \\ 2. CH_3CH_2Br}$$

Question 1

Which of the following statements best explains why the boiling point of ethanol is much higher than that of dimethyl ether, even though they have similar molecular weights?

Accepted Answer

Ethanol can form hydrogen bonds with itself, while dimethyl ether cannot.

Question 2

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

$$\mathrm{CH_3CH_2OCH_2CH_3}$$

Accepted Answer

Diethyl ether

Question 3

Which reagent(s) would you use to convert 1-butanol to butyl ethyl ether using the Williamson ether synthesis?

Accepted Answer

$$\mathrm{1. NaH \ 2. CH_3CH_2Br}$$

Question 4

Which of the following best describes the role of crown ethers in organic reactions?

Accepted Answer

They solvate metal cations, increasing the reactivity of the counterion.

Question 5

What is the major product when diethyl ether is treated with excess HI and heat?

Accepted Answer

$$\mathrm{2CH_3CH_2I + H_2O}$$

Question 6

Which of the following statements about the acid-catalyzed cleavage of ethers is correct?

Accepted Answer

Tertiary alkyl groups undergo cleavage via an $$S_N1$$ mechanism.

Question 7

Which reagent is commonly used to convert an alkene to an epoxide in a single step?

Accepted Answer

meta-Chloroperoxybenzoic acid (MCPBA)

Question 8

Which of the following best describes the stereochemistry of epoxidation of alkenes with MCPBA?

Accepted Answer

The reaction is stereospecific; cis-alkenes give cis-epoxides and trans-alkenes give trans-epoxides.

Question 9

Which of the following is a correct statement about the ring-opening of epoxides with strong nucleophiles?

Accepted Answer

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

Question 10

Which of the following best describes the product of the reaction between 1-bromo-2-hydroxycyclohexane and NaOH?

Accepted Answer

A cyclohexene oxide (epoxide)

Question 11

Which of the following is true about the ring-opening of epoxides under acidic conditions?

Accepted Answer

The nucleophile attacks the more substituted carbon if a tertiary carbon is present.

Question 12

Which of the following is the correct name for a compound with the structure $$\mathrm{CH_3CH_2CH_2SH}$$?

Accepted Answer

1-Propanethiol

Question 13

Which of the following best describes the preparation of sulfides?

Accepted Answer

Nucleophilic attack of a thiolate ion on an alkyl halide

Question 14

Which of the following is a correct statement about the formation of disulfides from thiols?

Accepted Answer

Disulfides are formed by oxidation of thiols.

Question 15

Which of the following best explains why 18-crown-6 is especially effective at solvating potassium ions ($$\mathrm{K^+}$$)?

Accepted Answer

The cavity size of 18-crown-6 matches the ionic radius of $$\mathrm{K^+}.$$

Question 16

Which of the following is the correct product when trans-2-butene is treated with MCPBA?

Accepted Answer

Trans-2,3-epoxybutane

Question 17

Which of the following statements about the stereochemistry of epoxide ring opening by a strong nucleophile is correct?

Accepted Answer

The configuration at the attacked carbon is inverted.

Question 18

Which of the following is a correct statement about the Markovnikov regioselectivity in alkoxymercuration-demercuration reactions?

Accepted Answer

The ether oxygen attaches to the more substituted carbon of the alkene.

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

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