Question 1

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

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 2

What is the major organic product when 2-butanol is treated with $$\mathrm{Na_2Cr_2O_7}$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-Butanone

Question 3

Which of the following alcohols cannot be oxidized by common oxidizing agents such as $$\mathrm{Na_2Cr_2O_7} or$$ $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

tert-Butanol

Question 4

What is the role of tosyl chloride ($$\mathrm{TsCl}) in $$the reaction with alcohols?

Accepted Answer

It converts the alcohol into a better leaving group.

Question 5

Which reagent is commonly used to convert a primary alcohol to a primary alkyl chloride via nucleophilic substitution?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 6

When 1-butanol is treated with $$\mathrm{H_2SO_4}$$ and heat, what is the major product?

Accepted Answer

2-Butene

Question 7

Which of the following statements best describes the Lucas reagent?

Accepted Answer

A mixture of $$\mathrm{HCl}$$ and $$\mathrm{$$ZnCl_2$$}$$ used to convert alcohols to alkyl chlorides.

Question 8

Which of the following is a correct mechanism step in the dehydration of alcohols using $$\mathrm{H_2SO_4}$$?

Accepted Answer

Formation of a carbocation intermediate after loss of water.

Question 9

Which reagent would you use to convert 1-butanol to 1-bromobutane?

Accepted Answer

$$\mathrm{HBr}$$

Question 10

What is the expected product when 1-butanol is treated with $$\mathrm{$$PBr_3$$}$$?

Accepted Answer

1-Bromobutane

Question 11

Which of the following is NOT a common oxidizing agent for alcohols?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 12

A student wants to convert 1-butanol to butanoic acid. Which reagent should they use?

Accepted Answer

$$\mathrm{Na_2Cr_2O_7}$$ / $$\mathrm{H_2SO_4}$$

Question 13

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

Accepted Answer

They are oxidized to ketones.

Question 14

What is the function of $$\mathrm{$$ZnCl_2$$} in $$the Lucas test for alcohols?

Accepted Answer

It coordinates to the OH group, making it a better leaving group.

Question 15

Which of the following alcohols reacts fastest with the Lucas reagent?

Accepted Answer

Tertiary alcohol

Question 16

What is the major product when 2-propanol is treated with $$\mathrm{$$SOCl_2$$}$$?

Accepted Answer

2-Chloropropane

Question 17

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

Accepted Answer

They make the alcohol group a good leaving group for substitution or elimination.

Question 18

A chemist wants to convert 1-butanol to 1-chlorobutane. Which reagent would be most effective?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 19

Which of the following is the correct order of increasing ease of dehydration of alcohols using $$\mathrm{H_2SO_4}$$?

Accepted Answer

Primary \u003c Secondary \u003c Tertiary

Question 20

Which of the following best describes the oxidation of a primary alcohol with $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

It produces a carboxylic acid.

Chapter 11: Reactions of Alcohols – Oxidation, Substitution, and Dehydration

Study Guide - Practice Questions