Question 1

Which of the following best explains why ethanol has a much higher boiling point than ethane and chloroethane?

Accepted Answer

Ethanol can form hydrogen bonds due to its $$-OH$$ group, which significantly increases its boiling point.

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{CH_3CH_2CH_2OH}$$?

Accepted Answer

1-Propanol

Question 3

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

Accepted Answer

PCC (pyridinium chlorochromate)

Question 4

Which of the following statements about the acidity of phenol compared to ethanol is correct?

Accepted Answer

Phenol is more acidic than ethanol due to resonance stabilization of the phenoxide ion.

Question 5

Which of the following is a correct statement about the preparation of alcohols using Grignard reagents?

Accepted Answer

Grignard reagents add to carbonyl compounds to form alcohols after hydrolysis.

Question 6

Why must alcohols be protected before performing a Grignard reaction, as shown in the second image?

Accepted Answer

Alcohols are strong acids and would protonate the Grignard reagent, destroying it.

Question 7

Which of the following reducing agents is strong enough to reduce esters and carboxylic acids to primary alcohols?

Accepted Answer

Lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$})$$

Question 8

Which of the following best describes the effect of electron-withdrawing groups on the acidity of alcohols and phenols?

Accepted Answer

Electron-withdrawing groups increase acidity by stabilizing the conjugate base through induction.

Question 9

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

Accepted Answer

Tertiary alcohols generally do not undergo oxidation because they lack an alpha proton.

Question 10

Which of the following is the correct product when 2-butanone is reduced with $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

2-Butanol

Question 11

Which of the following statements about the physical properties of alcohols is correct?

Accepted Answer

Alcohols have higher boiling points than alkanes due to hydrogen bonding.

Question 12

Which of the following is a correct statement about the Swern oxidation?

Accepted Answer

Swern oxidation uses DMSO and oxalyl chloride to oxidize alcohols without chromium.

Question 13

Which of the following best describes the mechanism by which sodium borohydride ($$\mathrm{$$NaBH_4$$}) $$reduces a carbonyl compound?

Accepted Answer

It delivers a hydride ($$\mathrm{H^-}) to $$the carbonyl carbon, followed by protonation from the solvent.

Question 14

Which of the following is a correct statement about the miscibility of alcohols in water?

Accepted Answer

Alcohols with three carbons or fewer are miscible in water.

Question 15

Which of the following is the correct product when phenol is oxidized?

Accepted Answer

Benzoquinone

Question 16

Which of the following statements about the use of protecting groups in alcohol chemistry is correct?

Accepted Answer

Protecting groups temporarily mask the reactivity of alcohols to allow selective reactions elsewhere in the molecule.

Question 17

Which of the following is a correct statement about the formation of Grignard reagents?

Accepted Answer

Grignard reagents are formed by reacting an alkyl halide with magnesium metal in anhydrous ether.

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

Study Guide - Practice Questions