Question 1

Which of the following best explains why ethanol has a much higher boiling point than ethane and chloroethane?

Accepted Answer

Ethanol can form hydrogen bonds due to its hydroxyl group, which significantly increases its boiling point.

Question 2

What is the correct IUPAC name for the following compound: CH3CH2CH(OH)CH3?

Accepted Answer

2-Butanol

Question 3

Which of the following statements about the acidity of phenol compared to cyclohexanol is correct?

Accepted Answer

Phenol is more acidic than cyclohexanol because its conjugate base is resonance stabilized.

Question 4

Which reagent would you use to selectively reduce an aldehyde to a primary alcohol without affecting an alkene present in the molecule?

Accepted Answer

$$\mathrm{$$NaBH_4$$}$$

Question 5

A student wants to synthesize 1-phenylethanol from benzaldehyde. Which sequence of reagents would accomplish this transformation?

Accepted Answer

1. $$\mathrm{CH_3MgBr}$$, 2. $$\mathrm{H_3O^+}$$

Question 6

Which of the following best describes the role of a protecting group in the synthesis of alcohols using Grignard reagents, as shown in the second image?

Accepted Answer

It prevents the alcohol from being deprotonated by the Grignard reagent, which would otherwise destroy the reagent.

Question 7

Which of the following alcohols would be most soluble in water?

Accepted Answer

Methanol ($$\mathrm{CH_3OH})$$

Question 8

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

Accepted Answer

Primary alcohols can be oxidized to aldehydes and then to carboxylic acids.

Question 9

Which reagent would you use to convert a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

$$\mathrm{PCC} ($$Pyridinium chlorochromate)

Question 10

Which of the following is a correct statement about the mechanism of the reaction between a Grignard reagent and a carbonyl compound?

Accepted Answer

The Grignard reagent acts as a nucleophile and attacks the electrophilic carbonyl carbon, forming a new C–C bond.

Question 11

Which of the following best explains why tert-butanol is less acidic than ethanol?

Accepted Answer

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

Question 12

Which of the following reagents can be used to convert a secondary alcohol to a ketone?

Accepted Answer

$$\mathrm{PCC}$$

Question 13

Which of the following statements about the physical properties of alcohols is correct?

Accepted Answer

Alcohols have higher boiling points than alkanes of similar molecular weight due to hydrogen bonding.

Question 14

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

Accepted Answer

Phenol is more readily oxidized than primary or secondary alcohols.

Question 15

Which of the following is a correct statement about the use of sodium borohydride ($$\mathrm{$$NaBH_4$$}) $$and lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$}) in $$organic synthesis?

Accepted Answer

$$\mathrm{$$LiAlH_4$$} is $$more reactive and can reduce esters and carboxylic acids, while $$\mathrm{$$NaBH_4$$}$$ generally cannot.

Question 16

Which of the following is a correct statement about the preparation of diols from alkenes?

Accepted Answer

Diols can be prepared from alkenes by syn-dihydroxylation using $$\mathrm{$$OsO_4$$} or$$ $$\mathrm{$$KMnO_4$$}.$$

Question 17

Which of the following is a correct statement about the use of tosylates in alcohol chemistry?

Accepted Answer

Tosylates convert the –OH group into a good leaving group, allowing for SN2 substitution reactions.

Question 18

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

Accepted Answer

Swern oxidation uses DMSO and oxalyl chloride to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.

Alcohols and Phenols: Properties, Preparation, and Reactions

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