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, increasing intermolecular forces.

Question 2

Which of the following alcohols is most acidic?

Accepted Answer

$$\mathrm{p{-}NO_2${-}C_6H_4OH} ($$para-nitrophenol)

Question 3

What is the correct IUPAC name for the following compound?

$$\mathrm{CH_3CH_2CH(OH)CH_3$}$$

Accepted Answer

2-butanol

Question 4

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

Accepted Answer

Lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$})$$

Question 5

Which of the following is the correct mechanism for the reaction of a Grignard reagent with a ketone?

Accepted Answer

Nucleophilic addition of $$\mathrm{R^-} to $$the carbonyl carbon, followed by protonation to give a tertiary alcohol.

Question 6

Which of the following statements about phenol is true?

Accepted Answer

Phenol is more acidic than regular alcohols because its conjugate base is stabilized by resonance.

Question 7

What is the product of the following reaction?

$$\mathrm{CH_3CH_2OH + NaH \rightarrow}$$

Accepted Answer

$$\mathrm{CH_3CH_2O^- Na^+}$$ + $$\mathrm{H_2$}$$

Question 8

Which of the following best describes the role of electron-withdrawing groups on the acidity of alcohols?

Accepted Answer

They stabilize the conjugate base by inductive effect, making the alcohol more acidic.

Question 9

Which of the following is NOT a correct statement about Grignard reagents?

Accepted Answer

They are stable in protic solvents such as water.

Question 10

Which of the following compounds is classified as a secondary alcohol?

Accepted Answer

$$\mathrm{CH_3CH(OH)CH_3$}$$

Question 11

Which of the following is the correct product when 2-butanone is reduced with sodium borohydride ($$\mathrm{$$NaBH_4$$}$$)?

Accepted Answer

2-butanol

Question 12

Which of the following statements about thiols is correct?

Accepted Answer

Thiols are more nucleophilic than alkoxides.

Question 13

What is the major product when a Grignard reagent ($$\mathrm{R{-}MgX}) $$reacts with an ester followed by aqueous workup?

Accepted Answer

A tertiary alcohol

Question 14

Which of the following is the correct order of increasing acidity for the following alcohols?

$$\mathrm{CH_3CH_2OH}$$, $$\mathrm{CH_3OH}$$, $$\mathrm{CF_3CH_2OH}$$

Accepted Answer

$$\mathrm{CH_3CH_2OH} \u003c \mathrm{CH_3OH} \u003c \mathrm{CF_3CH_2OH}$$

Question 15

Which of the following is the correct IUPAC name for ethylene glycol?

Accepted Answer

ethane-1,2-diol

Question 16

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 17

Which of the following is the best method to prepare sodium alkoxide ($$\mathrm{RO^-Na^+}) in $$high yield from an alcohol?

Accepted Answer

React the alcohol with sodium metal.

Question 18

Which of the following is a correct statement about the reactivity of sodium borohydride ($$\mathrm{$$NaBH_4$$}) $$compared to lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$}$$)?

Accepted Answer

$$\mathrm{$$NaBH_4$$} is $$milder and can only reduce aldehydes and ketones to alcohols.

Question 19

Which of the following is the correct product when 1-bromopentane reacts with sodium ethanethiolate ($$\mathrm{NaS{-}CH_2CH_3}$$)?

Accepted Answer

1-ethylthio-pentane ($$\mathrm{CH_3CH_2S{-}CH_2CH_2CH_2CH_2CH_3})$$

Structure and Synthesis of Alcohols and Thiols: Chapter 10 Study Notes

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