Question 1

Which of the following statements best explains why the Williamson ether synthesis fails when using tert-butyl iodide and methanol as shown in the first image?

Accepted Answer

Tert-butyl iodide undergoes elimination rather than substitution due to steric hindrance, making SN2 impossible.

Question 2

What is the product of the following reaction?

$$\ce{CH2=CH2} \xrightarrow{1)\ Hg(OAc)_2,\ H_2O \ 2)\ $$NaBH_4$$} $$

Accepted Answer

$$\ce{CH3CH2OH}$$

Question 3

Why must laboratory samples of ethers be tested for peroxides before use, as shown in the third image?

Accepted Answer

Ethers can form explosive hydroperoxides upon exposure to oxygen via a free radical mechanism.

Question 4

Which of the following best describes the stereochemistry of the product when cyclohexene is treated with $$\ce{Br2}$$ and $$\ce{H2O}$$, as shown in the fourth image?

Accepted Answer

A racemic mixture of trans-1-bromo-2-hydroxycyclohexane is formed.

Question 5

Which of the following is the correct mechanism for the oxidation of a thiol to a disulfide, as shown in the sixth image?

Accepted Answer

Deprotonation of the thiol to form a thiolate ion, followed by SN2 attack on a bromine atom.

Question 6

Which starting material would you use to synthesize a 1,2-diol from an alkene, as shown in the seventh image?

Accepted Answer

OsO$$_4 ($$osmium tetroxide)

Question 7

What is the IUPAC name for the compound shown in the eighth image?

Accepted Answer

Ethoxybenzene

Question 8

Which of the following reagents would convert phenol to ethoxybenzene, as shown in the ninth image?

Accepted Answer

1) NaOH 2) CH$$_3CH$_2I$$

Question 9

Which of the following best describes the product of the reaction of an epoxide with NaCN followed by H$$_3O$^+$$, as shown in the twelfth image?

Accepted Answer

A cyanohydrin with inversion of configuration at the less hindered carbon.

Question 10

When an epoxide is treated with ethanol in the presence of H$$_2SO$_4$$, as shown in the fifteenth image, what is the major product?

Accepted Answer

A trans-1-ethoxy-2-hydroxy product with inversion at the more substituted carbon.

Question 11

Which of the following statements about the reactivity of epoxides is correct?

Accepted Answer

Epoxides are more reactive than ethers due to ring strain.

Question 12

Which of the following best explains why crown ethers are useful in organic synthesis?

Accepted Answer

They solubilize metal cations in organic solvents by forming stable complexes.

Question 13

Which of the following is a correct statement about the regioselectivity of epoxide ring opening under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon via an SN2 mechanism.

Question 14

Which of the following is the correct product when 1-bromocyclohexane is treated with Mg in ether, followed by reaction with ethylene oxide and then acid workup?

Accepted Answer

2-cyclohexylethanol

Question 15

Which of the following best describes the oxidation of a sulfide to a sulfoxide?

Accepted Answer

It requires a mild oxidizing agent such as sodium metaperiodate.

Question 16

Which of the following is a correct statement about the Sharpless epoxidation?

Accepted Answer

It uses a chiral catalyst to produce enantioselective epoxidation of allylic alcohols.

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

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