Q: Which of the following correctly lists the acidity of the hydroxy hydrogen in phenol, cyclohexanol, and hexanol from least to most acidic?

Hexanol < cyclohexanol < phenol

Q: Which of the following best describes the effect of electron-withdrawing groups on the acidity of phenols?

They increase acidity by stabilizing the negative charge on the oxygen atom.

Q: Which of the following correctly lists methanol, isobutyl alcohol, and propanol in order of decreasing boiling point?

Isobutyl alcohol > propanol > methanol

Question 1

Which of the following best explains why alcohols have higher boiling points than their analogous alkanes?

Accepted Answer

Alcohols can form hydrogen bonds due to the presence of the hydroxyl group.

Question 2

Which of the following statements best explains why tertiary alcohols are resistant to oxidation under mild conditions?

Accepted Answer

There is no hydrogen attached to the carbon bearing the hydroxyl group.

Question 3

Which of the following correctly lists the acidity of the hydroxy hydrogen in phenol, cyclohexanol, and hexanol from least to most acidic?

Accepted Answer

Hexanol < cyclohexanol < phenol

Question 4

A student wants to oxidize 1-butanol to butanal without further oxidation to butanoic acid. Which reagent should they use?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 5

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

Accepted Answer

They increase acidity by stabilizing the negative charge on the oxygen atom.

Question 6

Which of the following is the correct IUPAC name for a molecule with a benzene ring, a hydroxyl group at carbon 1, and a methyl group at carbon 3?

Accepted Answer

m-methylphenol

Question 7

Which of the following correctly lists methanol, isobutyl alcohol, and propanol in order of decreasing boiling point?

Accepted Answer

Isobutyl alcohol > propanol > methanol

Question 8

Which of the following reagents can be used to convert cyclohexanol to cyclohexanone?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 9

A chemist wants to protect a carbonyl group in a molecule before performing a reduction. Which of the following is the most appropriate protecting group strategy?

Accepted Answer

Convert the carbonyl to an acetal or ketal using a diol and acid catalyst.

Question 10

Which of the following best describes the function of mesylates and tosylates in organic synthesis?

Accepted Answer

They are used to convert alcohols into better leaving groups for nucleophilic substitution.

Question 11

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

Accepted Answer

It uses $\mathrm{CrO_3}$ in aqueous sulfuric acid to oxidize primary alcohols to carboxylic acids.

Question 12

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

Accepted Answer

Phenols are more acidic than alcohols because the aromatic ring stabilizes the negative charge on the oxygen atom.

Question 13

Which of the following best describes the role of ubiquinone (coenzyme Q) in the electron transport chain?

Accepted Answer

It acts as an electron carrier, shuttling electrons between Complexes I/II and III.

Question 14

A researcher treats phenol with a strong oxidizing agent, followed by further oxidation with addition of hydroxyl groups. What is the final product?

Accepted Answer

A hydroxyquinone

Question 15

Which of the following is the correct sequence of steps to convert an aldehyde to an acetal?

Accepted Answer

React with two equivalents of an alcohol under acidic conditions

Question 16

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

Accepted Answer

Secondary alcohols can be oxidized to ketones by PCC or Jones reagent.

Question 17

A patient accidentally ingests methanol. Which toxic metabolite is primarily responsible for the resulting blindness?

Accepted Answer

Formic acid

Question 18

Which of the following best explains why primary alcohols are more acidic than tertiary alcohols?

Accepted Answer

Primary alcohols have fewer electron-donating alkyl groups, which stabilizes the alkoxide anion.

Question 19

Which of the following is the correct product when 1-phenylethanone is treated with ethylene glycol and acid?

Accepted Answer

A ketal

Question 20

Which of the following reagents can be used to deprotect an acetal back to a carbonyl compound?

Accepted Answer

Aqueous acid

Kaplan ch 5

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