Question 1

Which of the following best describes the difference between an alcohol, a phenol, and an enol?

Accepted Answer

An alcohol has an –OH group bonded to an sp3 carbon, a phenol has an –OH group bonded to an aromatic ring, and an enol has an –OH group bonded to an sp2 carbon of a double bond.

Question 2

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

Accepted Answer

Phenols are much more acidic than alcohols because the phenoxide ion is resonance-stabilized.

Question 3

Which reagent would you use to reduce a carboxylic acid to a primary alcohol?

Accepted Answer

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

Question 4

What is the major product when 2-methyl-2-propanol is dehydrated with concentrated $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-methylpropene

Question 5

Which of the following alcohols is most acidic?

Accepted Answer

$$\mathrm{CF_3CH_2OH}$$

Question 6

Which of the following best explains why tert-butyl alcohol is less acidic than methanol?

Accepted Answer

The tert-butoxide ion is sterically hindered and less easily solvated, making it less stable.

Question 7

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

(CH3)2CHCH(OH)CH2CH3

Accepted Answer

3-methyl-2-pentanol

Question 8

Which of the following statements about the Grignard reaction is FALSE?

Accepted Answer

Grignard reagents can be prepared from alkyl halides containing alcohol or carboxylic acid groups.

Question 9

Which of the following best describes the effect of an electron-withdrawing group on the acidity of phenol?

Accepted Answer

It increases the acidity by stabilizing the phenoxide ion through resonance and inductive effects.

Question 10

Which of the following is the correct product for the reaction of ethylene with water in the presence of $$\mathrm{H_3PO_4} at 250$$°C?

Accepted Answer

$$\mathrm{CH_3CH_2OH} ($$ethanol)

Question 11

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

Accepted Answer

Primary alcohols can be oxidized to aldehydes or carboxylic acids, while secondary alcohols are oxidized to ketones.

Question 12

Which of the following is a correct description of the IR absorption for an alcohol?

Accepted Answer

A broad O–H stretch at 3300–3400 $$\mathrm{cm$$^{-1}$$}$$ due to hydrogen bonding.

Question 13

Which of the following is the best method to protect an alcohol group during a Grignard reaction?

Accepted Answer

Convert the alcohol to a trialkylsilyl ether using $$\mathrm{Cl–$$SiR_3$$}$$ and a base.

Question 14

Which of the following is the correct product when 1-butanol is oxidized with Dess–Martin periodinane?

Accepted Answer

Butanal

Question 15

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 16

Which of the following is the correct product when cyclohexanol reacts with sodium hydride ($$\mathrm{NaH}$$)?

Accepted Answer

Sodium cyclohexanolate ($$\mathrm{C_6H_{11}O^- Na^+}) $$and hydrogen gas

Question 17

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

A benzene ring with a methyl group at position 1, a bromine at position 2, and a hydroxyl group at position 4.

Accepted Answer

2-bromo-4-methylphenol

Alcohols and Phenols: Structure, Nomenclature, Properties, and Synthesis

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