Question 1

Which of the following compounds can form hydrogen bonds with itself, resulting in a higher boiling point compared to the others?

Accepted Answer

CH3CH2OH (Ethyl alcohol)

Question 2

Which statement best explains why 1-heptanol is less soluble in water than methanol?

Accepted Answer

The hydrocarbon portion of 1-heptanol is much larger, making it more alkane-like and less able to hydrogen bond with water.

Question 3

Which of the following is the correct IUPAC name for the compound with the structure $$\mathrm{CH_3CH_2OCH_2CH_2OH}$$?

Accepted Answer

2-Ethoxyethanol

Question 4

What is the major product when 2-butanol undergoes dehydration in the presence of $$\mathrm{H_2SO_4}$$ catalyst?

Accepted Answer

2-Butene

Question 5

Which of the following alcohols can be oxidized to a ketone, but not to a carboxylic acid?

Accepted Answer

A secondary alcohol

Question 6

Which of the following best describes the oxidation of 1-butanol?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2OH} \xrightarrow{[O]} \mathrm{CH_3CH_2CH_2CHO} \xrightarrow{[O]} \mathrm{CH_3CH_2CH_2COOH}$$

Question 7

Which of the following statements about ethers is TRUE?

Accepted Answer

Ethers have lower boiling points than alcohols of similar molecular mass because they cannot hydrogen bond with themselves.

Question 8

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

Accepted Answer

The phenoxide ion is stabilized by resonance in the aromatic ring, making phenol more acidic.

Question 9

Which of the following is a correct statement about the chemical reactivity of thiols compared to alcohols?

Accepted Answer

Thiols are more easily oxidized than alcohols, forming disulfides.

Question 10

Which of the following compounds would have the highest boiling point?

Accepted Answer

1,4-Butanediol ($$\mathrm{HOCH_2CH_2CH_2CH_2OH})$$

Question 11

Which of the following best describes the trend in boiling points for straight-chain alcohols as the number of carbons increases?

Accepted Answer

Boiling point increases as the number of carbons increases due to stronger London dispersion forces.

Question 12

Which of the following is the correct classification for the alcohol in the structure $$\mathrm{CH_3CH(OH)CH_3$}$$?

Accepted Answer

Secondary alcohol

Question 13

Which of the following is a correct statement about the combustion of alcohols and ethers?

Accepted Answer

Both alcohols and ethers combust in oxygen to form $$\mathrm{CO_2$}$$ and $$\mathrm{H_2O}.$$

Question 14

Which of the following is the correct product when two molecules of ethanol react under acidic conditions?

Accepted Answer

Diethyl ether and water

Question 15

Which of the following best explains why diethyl ether is a good solvent for many organic reactions?

Accepted Answer

It is relatively unreactive and can dissolve both polar and nonpolar substances.

Question 16

Which of the following is the correct IUPAC name for $$\mathrm{CH_3CH_2SCH_3}$$?

Accepted Answer

Ethyl methyl sulfide

Question 17

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

Accepted Answer

Phenols are more acidic than alcohols because their conjugate base is stabilized by resonance.

Question 18

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

Accepted Answer

Tertiary alcohols do not undergo oxidation under mild conditions.

Question 19

Which of the following best describes the structure of glycerol?

Accepted Answer

A three-carbon chain with an -OH group attached to each carbon

Study Guide: Alcohols, Phenols, Ethers, and Sulfur Compounds (Chapter 14)

Study Guide - Practice Questions