Question 1

Which reagent is commonly used to reduce a carbonyl group in an aldehyde or ketone to an alcohol?

Accepted Answer

NaBH$$_4$$

Question 2

What is the major product when 1-phenylethanone reacts with CH$$_3$$MgBr followed by aqueous workup?

Accepted Answer

2-phenyl-2-propanol

Question 3

Which of the following best describes the mechanism of nucleophilic addition to an aldehyde?

Accepted Answer

The nucleophile attacks the carbonyl carbon, followed by protonation of the oxygen.

Question 4

During acid-catalyzed epoxide ring opening, which atom is first protonated?

Accepted Answer

The oxygen atom of the epoxide

Question 5

Which of the following is a correct statement about the Grignard reaction?

Accepted Answer

It involves the addition of RMgX to a carbonyl compound to form an alcohol after hydrolysis.

Question 6

What is the product of the base-catalyzed ring opening of ethylene oxide with methoxide ion?

Accepted Answer

2-methoxyethanol

Question 7

Which of the following is the correct IUPAC name for the compound CH$$_3CH$_2OH$$?

Accepted Answer

Ethanol

Question 8

In the Wittig reaction, what is the role of the phosphonium ylide?

Accepted Answer

It acts as a nucleophile attacking the carbonyl carbon.

Question 9

Which reagent would you use to oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

PCC (Pyridinium chlorochromate)

Question 10

What is the expected product when cyclohexene oxide is treated with HBr?

Accepted Answer

Trans-1-bromo-2-cyclohexanol

Question 11

Which of the following statements about phenols is correct?

Accepted Answer

Phenols are more acidic than alcohols due to resonance stabilization of the phenoxide ion.

Question 12

Which of the following is a correct description of the hydration of an aldehyde using the Wittk-Kishner reaction?

Accepted Answer

It converts an aldehyde to an alkane by removing the carbonyl oxygen.

Question 13

Which of the following is the correct mechanism for the acid-catalyzed cleavage of ethers?

Accepted Answer

Protonation of the ether oxygen followed by nucleophilic attack and bond cleavage.

Question 14

What is the product of the nucleophilic addition of HCN to acetone?

Accepted Answer

2-hydroxy-2-methylpropanenitrile

Question 15

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

Accepted Answer

Secondary alcohols are oxidized to ketones.

Question 16

In the nucleophilic addition of water to an aldehyde, what is the intermediate formed before the final product?

Accepted Answer

A tetrahedral intermediate

Question 17

Which of the following is the correct product when benzaldehyde reacts with NaBH$$_4$$?

Accepted Answer

Benzyl alcohol

Question 18

Which of the following is a correct statement about the nucleophilic addition of amines to aldehydes?

Accepted Answer

Primary amines react with aldehydes to form imines.

Question 19

Which of the following is the correct product when propanal reacts with excess CH$$_3$$MgBr followed by hydrolysis?

Accepted Answer

2-methyl-2-butanol

Alcohols, Phenols, Ethers, Epoxides, Aldehydes, and Ketones: Structure, Reactions, and Mechanisms

Study Guide - Practice Questions