Question 1

Which of the following statements best explains why phenol is more acidic than ethanol?

Accepted Answer

The phenoxide ion formed after deprotonation is stabilized by resonance in phenol.

Question 2

Which reagent is commonly used to reduce a carboxylic acid to a primary alcohol?

Accepted Answer

LiAlH4 (lithium aluminum hydride)

Question 3

What is the major product when 2-methylbutan-2-ol undergoes dehydration in the presence of H2SO4 and heat?

Accepted Answer

2-Methylbut-2-ene

Question 4

Which of the following compounds will NOT undergo oxidation under typical conditions?

Accepted Answer

Tertiary alcohol

Question 5

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

$$\mathrm{HOCH_2CH_2OH}$$

Accepted Answer

Ethylene glycol

Question 6

Why does water have a higher boiling point than diethyl ether?

Accepted Answer

Water forms strong hydrogen bonds, while diethyl ether does not.

Question 7

Which of the following reactions is used to synthesize alcohols from alkenes?

Accepted Answer

Hydration with $$\mathrm{H_2O}$$ and $$\mathrm{H_2SO_4}$$ catalyst

Question 8

Which of the following is a property shared by both alcohols and phenols?

Accepted Answer

Both can form hydrogen bonds due to the presence of an -OH group.

Question 9

What is the product of the reaction between cyclopentanol and sodium hydride ($$\mathrm{NaH}$$), followed by methyl iodide ($$\mathrm{CH_3I}$$)?

Accepted Answer

Cyclopentyl methyl ether

Question 10

Which of the following statements about Grignard reagents is TRUE?

Accepted Answer

Grignard reagents are formed by reacting alkyl halides with magnesium in ether.

Question 11

Which of the following is the correct product when 1-methylcyclohexene reacts with water in the presence of $$\mathrm{H_2SO_4}$$ catalyst?

Accepted Answer

1-Methylcyclohexanol

Question 12

Which of the following best describes the role of hydrogen bonding in the boiling points of alcohols?

Accepted Answer

Hydrogen bonding increases the boiling point by requiring more energy to break intermolecular forces.

Question 13

Which of the following is the major product when tert-butyl cyclohexyl ether reacts with $$\mathrm{CF_3CO_2H} at$$ $$0^\circC$$?

Accepted Answer

Cyclohexanol

Question 14

Which of the following statements about the oxidation of alcohols is correct?

Accepted Answer

Primary alcohols can be oxidized to aldehydes and then to carboxylic acids.

Question 15

Which of the following is a correct statement about the reaction of epoxides with nucleophiles?

Accepted Answer

Nucleophiles attack the less hindered carbon of the epoxide ring in an $$\mathrm{S_N2}$$ reaction.

Question 16

Which of the following ethers is correctly named according to IUPAC rules?

Accepted Answer

Ethyl phenyl ether

Question 17

Which of the following is the correct formula for calculating the acid dissociation constant ($$K_a) of a $$weak acid?

Accepted Answer

$$K_a = \frac{[A^-][H_3O^+]}{[HA]}$$

Question 18

Which of the following statements best explains why nitrophenol is more acidic than phenol?

Accepted Answer

The nitro group withdraws electron density, stabilizing the phenoxide ion.

Question 19

Which of the following is a correct statement about the density of ice compared to liquid water at the melting point?

Accepted Answer

Ice is less dense than liquid water because its hydrogen bonds create an open lattice structure.

Alcohols, Phenols, Ethers, and Their Sulfur Analogs: Structure, Properties, and Reactions

Study Guide - Practice Questions