Question 1

Which of the following statements best explains why alcohols generally have higher boiling points than alkanes of similar molecular weight?

Accepted Answer

Alcohols can form hydrogen bonds between molecules, requiring more energy to separate them.

Question 2

What is the correct IUPAC name for the following compound?

$$\mathrm{CH_3CH_2CH(CH_2I)CH(OH)CH(CH_3$)_2}

($$Refer to the structure in the images above.)

Accepted Answer

3-(Iodomethyl)-2-isopropylpentan-1-ol

Question 3

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

Accepted Answer

tert-butyl alcohol

Question 4

Which of the following best describes the product of the reaction between ethylene oxide and a Grignard reagent ($$\mathrm{R-MgX}) $$followed by acid workup?

Accepted Answer

A primary alcohol with two additional carbon atoms compared to the original Grignard reagent

Question 5

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

Accepted Answer

Phenol is much more acidic than cyclohexanol because the phenoxide ion is resonance stabilized.

Question 6

Which reagent would you use to selectively reduce a ketone to a secondary alcohol without affecting an ester group in the same molecule?

Accepted Answer

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

Question 7

A student wants to synthesize 2-methylpropan-2-ol using a Grignard reagent and a carbonyl compound. Which combination below would achieve this goal?

Accepted Answer

Reacting methylmagnesium bromide with acetone, followed by acid workup

Question 8

Which of the following best describes the mechanism by which sodium borohydride ($$\mathrm{$$NaBH_4$$}) $$reduces a ketone?

Accepted Answer

Hydride transfer to the carbonyl carbon, followed by protonation of the resulting alkoxide

Question 9

Which of the following statements about the reaction of Grignard reagents with esters is correct?

Accepted Answer

Two equivalents of Grignard reagent are required to produce a tertiary alcohol.

Question 10

Which of the following is a correct statement about the physical properties of alcohols?

Accepted Answer

Alcohols can form hydrogen bonds, leading to higher boiling points than alkanes and ethers.

Question 11

Which of the following best explains why tert-butanol reacts faster with potassium metal than with sodium metal?

Accepted Answer

Potassium is a stronger reducing agent and reacts more readily with sterically hindered alcohols.

Question 12

Which of the following is the correct IUPAC name for the compound commonly known as isobutyl alcohol?

Accepted Answer

2-methylpropan-1-ol

Question 13

Which of the following statements about the synthesis of vicinal diols is correct?

Accepted Answer

Syn dihydroxylation of alkenes using $$\mathrm{$$OsO_4$$} or $$cold, dilute $$\mathrm{$$KMnO_4$$}$$ produces vicinal diols.

Question 14

Which of the following is a limitation when using Grignard reagents in organic synthesis?

Accepted Answer

They react with acidic protons such as $$\mathrm{O-H}$$, $$\mathrm{N-H}$$, or $$\mathrm{S-H}$$, which can destroy the reagent.

Question 15

Which of the following best describes the product of the reduction of an ester with lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$}) $$followed by acid workup?

Accepted Answer

A primary alcohol

Question 16

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

$$\mathrm{CH_3CH_2CH(OH)CH_2CH_3}$$

Accepted Answer

pentan-2-ol

Question 17

Which of the following statements about thiols is correct?

Accepted Answer

Thiols can be synthesized by SN2 reaction of alkyl halides with sodium hydrosulfide.

Question 18

Which of the following best explains why phenol is more acidic than cyclohexanol?

Accepted Answer

The negative charge on the phenoxide ion is delocalized by resonance over the aromatic ring.

Question 19

Which of the following is the correct product when a Grignard reagent reacts with formaldehyde followed by acid workup?

Accepted Answer

A primary alcohol

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

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