Question 1

Which of the following statements best explains why tertiary alcohols dehydrate more easily than secondary or primary alcohols under acidic conditions?

Accepted Answer

Tertiary alcohols form more stable carbocations during the E1 elimination mechanism.

Question 2

What is the major product when 2-methyl-2-butanol is dehydrated using concentrated $$H_2SO_4$$ and heat?

Accepted Answer

$$CH_3C(CH_3$)=$$CHCH_3$$ (2-methyl-2-butene)

Question 3

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

$$\begin{array}{c}
CH_3$-CH_2$-CH(OH)-CH_2$-CH_3$
\end{array}$$

Accepted Answer

3-pentanol

Question 4

During the acid-catalyzed opening of an epoxide, which carbon does the nucleophile preferentially attack?

Accepted Answer

The more substituted carbon of the epoxide ring

Question 5

Which reagent would best convert a primary alcohol to an alkyl bromide in the laboratory?

Accepted Answer

$$PBr_3$$

Question 6

A patient is treated for alcoholism with Antabuse (disulfiram). What is the biochemical basis for the unpleasant symptoms experienced if the patient consumes ethanol?

Accepted Answer

Accumulation of acetaldehyde due to inhibition of aldehyde dehydrogenase

Question 7

Which of the following best describes the leaving group ability of the following species (from best to worst)?

$$H_2O$$, $$OH^-$$, $$NH_2$$^-$$

Accepted Answer

$$H_2O \u003e OH^- \u003e NH_2$^-$$

Question 8

Which of the following statements about ethers is correct?

Accepted Answer

Ethers are generally unreactive toward nucleophilic substitution due to the poor leaving group ability of $$OR^-.$$

Question 9

Which of the following is the correct systematic name for the compound below?

$$\begin{array}{c}
CH_3CH_2OCH_2CH_3
\end{array}$$

Accepted Answer

Ethoxyethane

Question 10

A laboratory technician wants to methylate a nucleophile. Which reagent would be most effective for this purpose?

Accepted Answer

Methyl iodide ($$CH_3I)$$

Question 11

Which of the following best explains why epoxides are more reactive than ethers toward nucleophilic attack?

Accepted Answer

Epoxides have significant ring strain, increasing their free energy and reactivity.

Question 12

Which of the following is the correct product when 1-butanol is oxidized with sodium hypochlorite ($$NaOCl) at$$ $$0^\circ C$$?

Accepted Answer

Butanal ($$CH_3CH_2CH_2CHO)$$

Question 13

Which of the following best describes the nucleophilic attack on an epoxide under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon of the epoxide ring.

Question 14

Which of the following is a correct statement about the oxidation of tertiary alcohols?

Accepted Answer

Tertiary alcohols cannot be oxidized to carbonyl compounds because they lack a hydrogen on the carbon bearing the $$OH$$ group.

Question 15

Which of the following best explains why thiolate ions ($$RS^-) $$are better nucleophiles than alkoxide ions ($$RO^-) in $$protic solvents?

Accepted Answer

Thiolate ions are less solvated and more polarizable than alkoxide ions.

Question 16

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

$$\begin{array}{c}
CH_3CH_2CH_2SH
\end{array}$$

Accepted Answer

1-propanethiol

Question 17

Which of the following best describes the role of $$H_2SO_4 in $$the dehydration of alcohols?

Accepted Answer

$$H_2SO_4$$ acts as a catalyst by protonating the $$OH$$ group, making it a better leaving group.

Question 18

Which of the following is a correct statement about the use of methyl iodide ($$CH_3I) in $$organic synthesis?

Accepted Answer

Methyl iodide is an effective methylating agent because iodide is a good leaving group.

Question 19

Which of the following best explains why ethers are commonly used as solvents in organic reactions?

Accepted Answer

Ethers are relatively unreactive and have moderate boiling points.

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

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