Question 1

Which of the following alcohols is most soluble in water at 25°C?

Accepted Answer

tert-butyl alcohol

Question 2

Which reagent would you use to selectively reduce an ester to a primary alcohol?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$

Question 3

What is the product of the reaction between cyclohexanone and $$\mathrm{$$NaBH_4$$} in $$methanol?

Accepted Answer

Cyclohexanol

Question 4

Which of the following functional groups is incompatible with Grignard reagents?

Accepted Answer

Alcohol

Question 5

What is the major product when 2-methyl-2-butanol is treated with $$\mathrm{$$POCl_3$$}$$ and pyridine?

Accepted Answer

2-methyl-2-butene

Question 6

Which of the following best describes the product when a Grignard reagent reacts with formaldehyde followed by aqueous workup?

Accepted Answer

A primary alcohol

Question 7

Which protecting group is commonly used for alcohols in Grignard reactions?

Accepted Answer

Trimethylsilyl ether (TMS)

Question 8

What is the product of the oxidation of a primary alcohol with PCC?

Accepted Answer

Aldehyde

Question 9

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

Accepted Answer

Ethanol is more acidic than tert-butanol

Question 10

Which reaction sequence would convert 1-butanol to 1-bromobutane most efficiently?

Accepted Answer

Treat with $$\mathrm{$$PBr_3$$}$$

Question 11

Which of the following is the correct order of reactivity of alkyl halides with Grignard reagent formation?

Accepted Answer

I \u003e Br \u003e Cl \u003e F

Question 12

What is the product of the reaction of 2 equivalents of $$\mathrm{CH_3MgBr}$$ with ethyl acetate followed by aqueous workup?

Accepted Answer

tert-Butyl alcohol

Question 13

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

Accepted Answer

It uses $$\mathrm{DMSO}$$ and $$\mathrm{(COCl)_2} as $$reagents

Question 14

Which of the following best describes the mechanism of alcohol conversion to alkyl chloride using thionyl chloride ($$\mathrm{$$SOCl_2$$}$$)?

Accepted Answer

Nucleophilic substitution with inversion of configuration

Question 15

Which of the following alcohols will undergo the fastest dehydration to an alkene under acidic conditions?

Accepted Answer

tert-butanol

Question 16

What is the product of the reaction of 1,2-ethanediol with $$\mathrm{H_2SO_4} at 100$$°C?

Accepted Answer

Pinacolone (via pinacol rearrangement)

Question 17

Which of the following is a correct statement about the reduction of carboxylic acids with $$\mathrm{$$LiAlH_4$$}$$?

Accepted Answer

It produces primary alcohols

Question 18

Which of the following is the correct product when a Grignard reagent reacts with an epoxide followed by aqueous workup?

Accepted Answer

A primary alcohol with two more carbons than the Grignard reagent

Question 19

Which of the following is the best method to convert a secondary alcohol to a ketone?

Accepted Answer

Oxidation with PCC

Question 20

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

Accepted Answer

Protecting groups prevent unwanted reactions during multi-step synthesis

Alcohols: Structure, Properties, Synthesis, and Reactions

Study Guide - Practice Questions