Question 1

Which structural feature distinguishes a phenol from an alcohol?

Accepted Answer

The –OH group is bonded to an aromatic ring.

Question 2

Which of the following compounds is the most acidic?

Accepted Answer

Phenol

Question 3

Why are phenols more acidic than alcohols?

Accepted Answer

Phenols have a weaker O—H bond due to resonance stabilization of the phenoxide anion.

Question 4

Which reagent is commonly used to reduce aldehydes and ketones to alcohols?

Accepted Answer

NaBH4

Question 5

What is the product when a ketone is reduced with NaBH4?

Accepted Answer

A secondary alcohol

Question 6

Which of the following is the correct IUPAC name for the compound with three hydroxyl groups on a propane chain?

Accepted Answer

1,2,3-propanetriol

Question 7

Which alcohol is most likely to be insoluble in water?

Accepted Answer

Decanol

Question 8

What is the effect of converting an alcohol or phenol to its salt?

Accepted Answer

Increases water solubility

Question 9

Which of the following is a primary alcohol?

Accepted Answer

Ethanol

Question 10

What is the main reason tertiary alcohols do not react with most oxidizing agents?

Accepted Answer

They lack a hydrogen atom on the carbon bearing the –OH group.

Question 11

Which of the following reactions is used to convert a primary alcohol to an aldehyde?

Accepted Answer

Oxidation with gentle warming and distillation

Question 12

Which compound is found in Dettol and acts as a general disinfectant?

Accepted Answer

Phenol

Question 13

What is the effect of an electron-withdrawing substituent on the acidity of phenol?

Accepted Answer

It increases the acidity.

Question 14

Which of the following is the strongest acid?

Accepted Answer

Nitro phenol

Question 15

What is the mechanism for the reduction of a carbonyl compound to an alcohol?

Accepted Answer

Addition of a nucleophilic hydride ion to the carbonyl carbon, followed by protonation.

Question 16

Which reagent is best for converting primary and secondary alcohols into alkyl halides?

Accepted Answer

SOCl2 or PCl5

Question 17

Which functional group is responsible for the hydrophilicity of drug molecules containing alcohols?

Accepted Answer

The –OH group

Question 18

What is the product of the oxidation of a secondary alcohol?

Accepted Answer

A ketone

Question 19

Which of the following statements about alcohols and phenols is correct?

Accepted Answer

They are weakly acidic and do not react with weak bases.

Question 20

Which synthetic method is most commonly used to produce alcohols from carbonyl compounds?

Accepted Answer

Reduction

Alcohols and Phenols: Structure, Properties, Synthesis, and Reactions

Study Guide - Practice Questions