Question 1

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

Accepted Answer

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

Question 2

What is the IUPAC name for the following compound: $$CH_3CH_2CH_2CH_2OH$$?

Accepted Answer

1-Butanol

Question 3

Which of the following alcohols is classified as a tertiary alcohol?

Accepted Answer

$$(CH_3$)_3COH$$

Question 4

Which functional group has the highest priority in IUPAC nomenclature?

Accepted Answer

Acid

Question 5

Why does the solubility of alcohols in water decrease as the size of the alkyl group increases?

Accepted Answer

The hydrophobic (nonpolar) region of the molecule increases, reducing hydrogen bonding with water.

Question 6

Which of the following reagents can be used to synthesize a vicinal diol from an alkene via syn addition?

Accepted Answer

$$OsO_4$$ and $$H_2O_2$$

Question 7

What is the major organic product when 2-propanol reacts with sodium metal?

Accepted Answer

Sodium isopropoxide and hydrogen gas

Question 8

Which of the following statements about phenol is TRUE?

Accepted Answer

Phenol is more acidic than cyclohexanol due to resonance stabilization of the phenoxide ion.

Question 9

Which of the following reactions will produce a secondary alcohol?

Accepted Answer

Reduction of a ketone with $$NaBH_4$$

Question 10

A Grignard reagent is prepared by reacting an alkyl halide with magnesium in dry ether. Which of the following is the correct general formula for a Grignard reagent?

Accepted Answer

$$R-Mg-X$$

Question 11

Which of the following sequences will NOT produce an alcohol or diol from an alkene starting material?

Accepted Answer

$$CH_3CO_2H$$

Question 12

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

Accepted Answer

Halogens and other electron-withdrawing groups increase the acidity of alcohols.

Question 13

What is the product of the reaction between $$CH_3CH_2MgBr$$ and formaldehyde followed by aqueous workup?

Accepted Answer

1-Butanol

Question 14

Which reagent is most selective for reducing aldehydes and ketones but not esters or carboxylic acids?

Accepted Answer

$$NaBH_4$$

Question 15

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

Accepted Answer

Two moles of Grignard reagent react with an ester to give a tertiary alcohol.

Question 16

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

$$\mathrm{CH_3CH(OH)CH_2CH_3}$$

Accepted Answer

2-Butanol

Question 17

Which of the following statements about thiols is TRUE?

Accepted Answer

Thiols are easily oxidized to disulfides.

Question 18

Which of the following best describes the product of the reaction between a Grignard reagent and ethylene oxide followed by aqueous workup?

Accepted Answer

An alcohol with two more carbon atoms than the Grignard reagent

Question 19

Which of the following is a correct statement about the resonance stabilization of the phenoxide ion?

Accepted Answer

The negative charge is delocalized over four atoms in the phenoxide ion.

Question 20

Which of the following sequences would best facilitate the conversion of an alkene to a secondary alcohol?

Accepted Answer

1. $$Hg(OAc)_2$$, $$H_2O$$; 2. $$NaBH_4$$

Structure and Synthesis of Alcohols – Study Notes

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