Question 1

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

Accepted Answer

The phenoxide ion formed from phenol is resonance-stabilized, spreading the negative charge over the aromatic ring.

Question 2

Which reagent is most suitable for the reduction of a ketone to a secondary alcohol?

Accepted Answer

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

Question 3

What is the IUPAC name for the compound with the following structure: $$\mathrm{CH_2OH-CHOH-CH_2OH}$$?

Accepted Answer

1,2,3-propanetriol

Question 4

Which of the following statements about the solubility of alcohols in water is correct?

Accepted Answer

Water solubility decreases as the non-polar hydrocarbon chain length increases.

Question 5

Which of the following alcohols can be oxidized to a ketone?

Accepted Answer

Secondary alcohol

Question 6

Which of the following is the strongest acid?

Accepted Answer

Phenol

Question 7

What is the product when 2-propanol is oxidized with potassium dichromate ($$\mathrm{K_2Cr_2O_7}) in $$acidic solution?

Accepted Answer

Acetone (propanone)

Question 8

Which of the following best describes the reaction mechanism for the reduction of a carbonyl compound to an alcohol using $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

Nucleophilic addition of hydride ion followed by protonation

Question 9

Which of the following compounds is most likely to be found as an ingredient in antiseptic solutions such as Dettol or TCP?

Accepted Answer

Phenol

Question 10

Which of the following statements about the acidity of substituted phenols is correct?

Accepted Answer

Electron-withdrawing groups increase the acidity of phenol.

Question 11

Which of the following is a correct classification for 2-methyl-2-propanol?

Accepted Answer

Tertiary alcohol

Question 12

Which of the following reagents is commonly used to convert a primary or secondary alcohol into an alkyl chloride?

Accepted Answer

$$\mathrm{$$SOCl_2$$} ($$thionyl chloride)

Question 13

Which of the following best describes the effect of converting an alcohol or phenol to its salt?

Accepted Answer

It increases water solubility due to ion-dipole interactions.

Question 14

Which of the following is a product of the reduction of a carboxylic acid with $$\mathrm{$$LiAlH_4$$}$$?

Accepted Answer

A primary alcohol

Question 15

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

Accepted Answer

They have higher boiling points due to hydrogen bonding.

Question 16

Which of the following reactions will NOT occur with a tertiary alcohol under normal conditions?

Accepted Answer

Oxidation to a ketone

Question 17

Which of the following is a correct description of an enol?

Accepted Answer

A compound with an $$-OH$$ group bonded to a vinylic, $$sp^2-$$hybridized$$ $$ carbon

Question 18

Which of the following best explains why methanol is toxic to humans?

Accepted Answer

It is metabolized to formaldehyde and formic acid, which are toxic to the optic nerve and central nervous system.

Question 19

Which of the following is the correct sequence for the oxidation of a primary alcohol using $$\mathrm{K_2Cr_2O_7}$$ and $$\mathrm{H_2SO_4}$$ under reflux?

Accepted Answer

Primary alcohol $$\rightarrow$$ aldehyde $$\rightarrow$$ carboxylic acid

Alcohols and Phenols: Structure, Properties, Synthesis, and Reactions

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