Question 1

Which of the following statements best describes the geometry around the oxygen atom in diethyl ether?

Accepted Answer

It is bent with a bond angle close to 112° due to sp3 hybridization.

Question 2

Which reagent combination is most appropriate for the Williamson ether synthesis of cyclopentyl methyl ether?

Accepted Answer

Cyclopentanol and methyl iodide in the presence of NaH.

Question 3

In the acidic cleavage of ethers, which product is formed when isopropyl methyl ether reacts with HI?

Accepted Answer

Isopropyl alcohol and methyl iodide

Question 4

Which of the following ethers can be synthesized using the alkoxymercuration of alkenes?

Accepted Answer

Ethyl phenyl ether

Question 5

What is the major product when 1,2-epoxypropane is treated with HCl?

Accepted Answer

1-Chloro-2-propanol

Question 6

Which nucleophile would you use to convert an alkyl halide to a thiol via an $S_N2$ reaction?

Accepted Answer

HS-

Question 7

What is the product of the oxidation of two molecules of cyclohexanethiol with Br$_2$?

Accepted Answer

Cyclohexyl disulfide

Question 8

Which statement best explains why sulfur compounds are more nucleophilic than their oxygen analogs?

Accepted Answer

Sulfur is less electronegative and has larger, more polarizable orbitals.

Question 9

Which of the following is a correct description of the Williamson ether synthesis mechanism?

Accepted Answer

It requires a primary or secondary alkyl halide and an alkoxide ion.

Question 10

What is the role of NaH in the Williamson ether synthesis?

Accepted Answer

It deprotonates the alcohol to form the alkoxide ion.

Question 11

Which of the following is a correct product of the reaction of methyl phenyl sulfide with iodomethane?

Accepted Answer

Phenylmethylsulfonium ion

Question 12

Which of the following solvents is a polar aprotic solvent that can penetrate the skin and carry dissolved substances?

Accepted Answer

Dimethyl sulfoxide (DMSO)

Question 13

What is the major product when tert-butyl methyl ether undergoes acidic cleavage with HI?

Accepted Answer

tert-Butyl iodide and methanol

Question 14

Which of the following best describes the product of the reaction between an epoxide and a Grignard reagent?

Accepted Answer

An alcohol with a new carbon-carbon bond

Question 15

Which of the following is a correct statement about the IR spectrum of ethers?

Accepted Answer

Ethers show a C-O stretch near 1100 cm$^{-1}$.

Question 16

Which of the following is a correct product of the reaction of 1-octanethiol with Br$_2$?

Accepted Answer

1,1'-Dioctyl disulfide

Question 17

Which of the following is a correct description of the ring-opening of epoxides under acidic conditions?

Accepted Answer

The nucleophile attacks the more substituted carbon.

Question 18

Which of the following is a correct statement about thiols compared to alcohols?

Accepted Answer

Thiols are more acidic than alcohols.

Question 19

Which of the following is a correct product of the reaction of an enolate ion with an alkyl halide?

Accepted Answer

An α-alkylated carbonyl compound

Chapter 18: Ethers, Epoxides, Thiols, and Sulfides – Structures, Synthesis, and Reactions

Study Guide - Practice Questions