$\text{methanol} > \text{1-propanol} > \text{2-propanol} > \text{tert-butanol}$

Question 1

Which of the following statements best explains why phenols are more acidic than aliphatic alcohols?

Accepted Answer

The benzene ring in phenols stabilizes the negative charge of the phenoxide ion through resonance.

Question 2

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

Accepted Answer

Pyridinium chlorochromate (PCC) in CH$_2$Cl$_2$

Question 3

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

Accepted Answer

CH$_3$CH$_2$CH$_2$CH$_2$CH$_2$CH$_2$CH$_2$OH

Question 4

What is the major product when 2-butanol is treated with concentrated H$_2$SO$_4$ and heated?

Accepted Answer

2-butene

Question 5

Which of the following statements about Grignard reagents is TRUE?

Accepted Answer

Grignard reagents are incompatible with water and alcohols because they are strong bases.

Question 6

Which of the following best describes the effect of electron-withdrawing substituents on the acidity of phenols?

Accepted Answer

They increase the acidity by stabilizing the negative charge on the phenoxide ion through resonance and inductive effects.

Question 7

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

Accepted Answer

2-methyl-2-propanol

Question 8

What is the product when 1-butanol is treated with PCC in CH$_2$Cl$_2$?

Accepted Answer

Butanal

Question 9

Which of the following is the correct order of acidity for the following alcohols: methanol, 1-propanol, 2-propanol, and tert-butanol?

Accepted Answer

$	ext{methanol} > 	ext{1-propanol} > 	ext{2-propanol} > 	ext{tert-butanol}$

Question 10

Which of the following reactions will convert an alcohol to an alkyl bromide with inversion of stereochemistry?

Accepted Answer

Treatment with PBr$_3$

Question 11

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

Accepted Answer

Hydrogen bonding in alcohols is responsible for their higher boiling points compared to similar alkanes.

Question 12

Which of the following is a correct statement about the SN$_1$ reaction of alcohols with HX?

Accepted Answer

It involves a carbocation intermediate and can lead to rearrangements and racemization.

Question 13

Which of the following is a reason why tosylates are useful in organic synthesis?

Accepted Answer

Formation of tosylates does not affect the stereochemistry of the carbon attached to the alcohol.

Question 14

A student wants to prepare 2-butanol from an aldehyde using a Grignard reagent. Which starting material and reagent should they use?

Accepted Answer

Butanal and CH$_3$MgBr

Question 15

Which of the following functional groups is incompatible with Grignard reagents due to their strong basicity?

Accepted Answer

Carboxylic acid

Question 16

Which of the following best describes the role of a protecting group in alcohol chemistry?

Accepted Answer

It temporarily converts the hydroxyl group into a new functional group compatible with reaction conditions.

Question 17

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

Accepted Answer

Tertiary alcohols are resistant to oxidation under normal conditions.

Question 18

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

CH$_3$CH(OH)CH$_2$CH$_3$

Accepted Answer

2-butanol

Question 19

Which of the following best explains why methanol is more acidic than tert-butanol?

Accepted Answer

Methanol has less steric hindrance, allowing better solvation of the alkoxide ion.

Question 20

Which of the following reagents will reduce a ketone to a secondary alcohol?

Accepted Answer

NaBH$_4$

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

Study Guide - Practice Questions