Question 1

Which of the following best describes the functional group present in all alcohols?

Accepted Answer

A hydroxyl group ($$-OH) $$attached to an $$sp^3$$ hybridized carbon

Question 2

Which of the following alcohols is classified as a secondary alcohol?

Accepted Answer

2-Propanol

Question 3

According to IUPAC nomenclature, what is the correct name for the following compound: $$CH_3CH_2CH(OH)CH_3$?

Accepted Answer

2-Butanol

Question 4

Which of the following statements about the boiling points of alcohols is correct?

Accepted Answer

Alcohols have higher boiling points than alkanes of similar molecular weight due to hydrogen bonding.

Question 5

Which compound is more soluble in water: 1-octanol or ethanol? Why?

Accepted Answer

Ethanol, because it has a shorter hydrocarbon chain and can form more hydrogen bonds with water

Question 6

Which of the following factors increases the acidity of an alcohol?

Accepted Answer

Presence of electron-withdrawing groups such as halogens

Question 7

Why is phenol much more acidic than typical alcohols?

Accepted Answer

Because the phenoxide ion is stabilized by resonance delocalization

Question 8

Which reagent would you use to convert a primary alkyl halide to a primary alcohol via an $$S_N2$$ mechanism?

Accepted Answer

$$NaOH$$

Question 9

Which set of reagents would you use to hydrate an alkene to form an alcohol with anti-Markovnikov regioselectivity?

Accepted Answer

1) $$BH_3$$, THF; 2) $$H_2O_2$$, $$NaOH$$

Question 10

What is the major product when 2-butanol is treated with $$HBr$$?

Accepted Answer

2-Bromobutane via an $$S_N1$$ mechanism

Question 11

Which of the following reagents will convert a secondary alcohol to a ketone without further oxidation?

Accepted Answer

PCC (pyridinium chlorochromate)

Question 12

What is the expected stereochemical outcome when a chiral secondary alcohol is converted to a bromide using $$PBr_3$$?

Accepted Answer

Inversion of configuration

Question 13

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

Accepted Answer

Secondary and tertiary alcohols dehydrate via an $$E1$$ mechanism

Question 14

Which reagent is commonly used to convert a primary alcohol to a tosylate, and what is the advantage of this transformation?

Accepted Answer

$$p-$$Toluenesulfonyl chloride (TsCl); it makes the hydroxyl group a better leaving group

Question 15

A student wants to oxidize 1-butanol to butanal without further oxidation to butanoic acid. Which reagent should they use?

Accepted Answer

PCC (pyridinium chlorochromate)

Question 16

Which of the following alcohols cannot be oxidized under normal laboratory conditions?

Accepted Answer

tert-Butanol

Question 17

What is the product of the reaction of 1-butanol with $$SOCl_2 in $$the presence of pyridine?

Accepted Answer

1-Chlorobutane with inversion of configuration

Question 18

Which of the following best explains why tertiary alcohols react faster with $$HX$$ than primary alcohols?

Accepted Answer

Tertiary alcohols form more stable carbocations, favoring the $$S_N1$$ mechanism

Question 19

Which of the following is the correct order of acidity for alcohols?

Accepted Answer

Methanol \u003e Primary \u003e Secondary \u003e Tertiary

Alcohols: Structure, Properties, Nomenclature, and Reactions

Study Guide - Practice Questions