Question 1

Which of the following best describes a secondary (2°) alcohol?

Accepted Answer

The carbon bearing the —OH group is attached to two other carbon atoms and one hydrogen atom.

Question 2

Which compound is classified as a triol?

Accepted Answer

1,2,3-Propanetriol (Glycerol)

Question 3

What is the primary reason ethanol has a much higher boiling point than dimethyl ether, despite having similar molecular weights?

Accepted Answer

Ethanol can form intermolecular hydrogen bonds due to its O—H group.

Question 4

Arrange the following compounds in order of increasing boiling point: hexane, 1-pentanol, 1,4-butanediol.

Accepted Answer

Hexane \u003c 1-pentanol \u003c 1,4-butanediol

Question 5

Which of the following statements about hydrogen bonding in alcohols is correct?

Accepted Answer

Hydrogen bonding increases the boiling point of alcohols compared to alkanes and ethers.

Question 6

What is the major product when 2-butanol undergoes acid-catalyzed dehydration?

Accepted Answer

$$(E	ext{ and }Z)-2-$$Butene

Question 7

Which reagent is most selective for oxidizing primary alcohols to aldehydes without further oxidation to carboxylic acids?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 8

Which alcohol is resistant to oxidation under typical conditions?

Accepted Answer

Tertiary (3°) alcohol

Question 9

In the SN1 reaction of a tertiary alcohol with HBr, what is the rate-determining step?

Accepted Answer

Formation of the carbocation intermediate

Question 10

Which of the following best describes the Zaitsev rule in the acid-catalyzed dehydration of alcohols?

Accepted Answer

The more substituted alkene is the major product.

Question 11

What is the functional group present in thiols?

Accepted Answer

Sulfhydryl group ($$\mathrm{–SH})$$

Question 12

Which compound is most likely to be oxidized to a disulfide in biological systems?

Accepted Answer

A thiol ($$\mathrm{R–SH})$$

Question 13

Which of the following is a correct IUPAC name for a compound with two hydroxyl groups on adjacent carbons?

Accepted Answer

1,2-Ethanediol

Question 14

What is the product when 1-hexanol is oxidized with chromic acid ($$\mathrm{H_2CrO_4}) in $$aqueous solution?

Accepted Answer

Hexanoic acid

Question 15

Which of the following statements about the solubility of alcohols in water is correct?

Accepted Answer

Alcohols with lower molecular weight are more soluble in water.

Question 16

Which mechanism is most likely for the dehydration of a secondary alcohol under acidic conditions?

Accepted Answer

E1 mechanism involving carbocation formation

Question 17

What is the major product when 3,3-dimethyl-2-butanol is dehydrated with sulfuric acid?

Accepted Answer

2,3-Dimethyl-2-butene

Question 18

Which of the following is true about the oxidation of secondary alcohols with chromic acid?

Accepted Answer

Secondary alcohols are oxidized to ketones.

Question 19

Which of the following best explains why tertiary alcohols are resistant to oxidation?

Accepted Answer

The carbon bearing the —OH group lacks a hydrogen atom necessary for oxidation.

Question 20

Which of the following is the correct product when geraniol is oxidized with PCC?

Accepted Answer

Geranial

Alcohols and Thiols: Structure, Properties, and Reactions

Study Guide - Practice Questions