Question 1

Which of the following reagents can selectively oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 2

A student treats cyclohexanol with $$\mathrm{NaOCl}$$ and acetic acid. What is the major organic product?

Accepted Answer

Cyclohexanone

Question 3

Which of the following statements best describes the difference between the oxidation of a secondary alcohol and a tertiary alcohol?

Accepted Answer

Secondary alcohols are oxidized to ketones, while tertiary alcohols are resistant to oxidation under normal conditions.

Question 4

What is the role of ZnCl$$_2 in $$the Lucas reagent when reacting with alcohols?

Accepted Answer

It coordinates with the alcohol oxygen, making the hydroxyl group a better leaving group.

Question 5

Which of the following alcohols will react fastest with the Lucas reagent (HCl/ZnCl$$_2$$)?

Accepted Answer

tert-butanol

Question 6

A chemist wants to convert 2-butanol to 2-bromobutane. Which sequence of reagents would be most efficient?

Accepted Answer

HBr

Question 7

Which of the following best explains why tertiary alcohols do not undergo oxidation under mild conditions?

Accepted Answer

They lack a hydrogen atom on the carbon bearing the hydroxyl group.

Question 8

What is the major organic product when (R)-2-butanol is treated with TsCl/pyridine followed by NaI?

Accepted Answer

(S)-2-iodobutane

Question 9

Which of the following is a limitation of using HX (HCl or HBr) to convert alcohols to alkyl halides?

Accepted Answer

Carbocation rearrangements can occur, leading to unexpected products.

Question 10

A vicinal diol is treated with periodic acid ($$\mathrm{$$HIO_4$$}). $$What is the expected outcome?

Accepted Answer

Cleavage to give two carbonyl compounds

Question 11

Which of the following reagents would best convert a primary alcohol to a carboxylic acid in one step?

Accepted Answer

NaOCl (excess) with TEMPO

Question 12

What is the major product when cyclopentanol is treated with 1. NH$$_3 2. CH$_3CH$_2Br$$?

Accepted Answer

N-ethylcyclopentylamine

Question 13

Which of the following best describes the mechanism for the dehydration of a secondary alcohol with concentrated sulfuric acid?

Accepted Answer

E1 elimination involving carbocation rearrangement

Question 14

A student wants to synthesize an ether from ethanol and 1-bromopropane. Which method is most appropriate?

Accepted Answer

Williamson ether synthesis using sodium ethoxide

Question 15

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

Accepted Answer

It uses DMSO and oxalyl chloride to oxidize alcohols to aldehydes or ketones.

Question 16

What is the product when 2-methyl-2-butanol is treated with concentrated HBr?

Accepted Answer

2-bromo-2-methylbutane

Question 17

Which of the following best describes the function of a tosylate group in organic synthesis?

Accepted Answer

It is an excellent leaving group, facilitating substitution and elimination reactions.

Question 18

Which of the following reagents would NOT be suitable for oxidizing a secondary alcohol to a ketone?

Accepted Answer

LiAlH$$_4$$

Question 19

What is the expected product when ethylene glycol (a vicinal diol) is treated with periodic acid ($$\mathrm{$$HIO_4$$}$$)?

Accepted Answer

Two molecules of formaldehyde

Question 20

Which of the following statements about the Fischer esterification is correct?

Accepted Answer

It is an equilibrium reaction between a carboxylic acid and an alcohol.

Reactions of Alcohols – Oxidation, Substitution, and Related Transformations

Study Guide - Practice Questions