Question 1

Which functional group is present in both tetrahydrocannabinol (THC) and dopamine, as shown in the images above?

Accepted Answer

Phenol

Question 2

Which of the following best explains why phenols are more acidic than alcohols?

Accepted Answer

The conjugate base of phenol is stabilized by resonance with the aromatic ring.

Question 3

Which of the following is the correct classification for an alcohol with the structure $$\mathrm{CH_3CH_2CH_2OH}$$?

Accepted Answer

Primary alcohol

Question 4

Which reaction mechanism is most likely for the synthesis of a tertiary alcohol from a tertiary alkyl halide and water?

Accepted Answer

$$S_N1$$

Question 5

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

Accepted Answer

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

Question 6

What is the oxidation state of carbon in methanol ($$\mathrm{CH_3OH}$$)?

Accepted Answer

$$-2$$

Question 7

Which of the following statements about Grignard reagents is TRUE?

Accepted Answer

They form new C–C bonds by acting as nucleophiles.

Question 8

Which of the following best describes the product when a Grignard reagent reacts with an ester?

Accepted Answer

A tertiary alcohol

Question 9

Which of the following is a correct statement about the reduction of carboxylic acids with $$\mathrm{$$LiAlH_4$$}$$?

Accepted Answer

Carboxylic acids are reduced to primary alcohols.

Question 10

Which of the following best explains why Grignard reagents cannot be used in the presence of water?

Accepted Answer

They react with water to form alkanes and lose their nucleophilicity.

Question 11

Which of the following methods would produce a syn diol from an alkene?

Accepted Answer

Catalytic $$\mathrm{$$OsO_4$$}$$ with NMO

Question 12

Which of the following is the correct order of increasing stability for the conjugate bases shown in the stability diagram?

Accepted Answer

$$\mathrm{R:^- \u003c RNH^- \u003c RO^- \u003c X^-}$$

Question 13

Which of the following statements about sodium borohydride ($$\mathrm{$$NaBH_4$$}) is $$correct?

Accepted Answer

It reduces ketones and aldehydes to alcohols.

Question 14

Which of the following is a product of the acid-catalyzed hydration of 1-butene?

Accepted Answer

2-butanol

Question 15

Which of the following best describes the stereochemical outcome when a chiral alcohol is formed by the reduction of a ketone with $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

A racemic mixture of both enantiomers is formed.

Question 16

Which of the following statements about the hydroboration-oxidation of alkenes is correct?

Accepted Answer

It adds water in an anti-Markovnikov fashion.

Question 17

Which of the following is a correct statement about the reaction of a Grignard reagent with a ketone?

Accepted Answer

It produces a tertiary alcohol.

Question 18

Which of the following is a reason why phenols are found in many biologically active molecules such as dopamine and THC?

Accepted Answer

Phenols are more acidic and can participate in hydrogen bonding and electron delocalization.

Alcohols and Phenols: Structure, Properties, and Synthesis

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