Q: Which of the following is the correct order of acidity for the following compounds: acetic acid, ethanol, and phenol?

$$ \text{acetic acid} \u003e \text{phenol} \u003e \text{ethanol} $$

Question 1

Which of the following statements best describes the mechanism of the aldol condensation between acetaldehyde and benzaldehyde under basic conditions?

Accepted Answer

The reaction proceeds via nucleophilic addition of the enolate ion of acetaldehyde to the carbonyl carbon of benzaldehyde, followed by dehydration to yield an α,β-unsaturated carbonyl compound.

Question 2

Which reagent would best convert a carboxylic acid to its corresponding acid chloride?

Accepted Answer

$$ 	ext{SOCl}_2 $$

Question 3

A student attempts to synthesize ethyl acetate from ethanol and acetic acid. Which catalyst would most efficiently drive this Fischer esterification reaction to completion?

Accepted Answer

$$ 	ext{H}_2	ext{SO}_4 $$

Question 4

Which of the following compounds will undergo decarboxylation most readily upon heating?

Accepted Answer

$$ \beta -$$Keto acids

Question 5

In the malonic ester synthesis, what is the role of sodium ethoxide ($$ 	ext{NaOEt} $$)?

Accepted Answer

It deprotonates the methylene group between the two carbonyls, generating an enolate ion.

Question 6

Which product is formed when benzaldehyde reacts with acetone in the presence of a base?

Accepted Answer

An α,β-unsaturated ketone via crossed aldol condensation

Question 7

Which of the following best explains why acyl chlorides are more reactive than esters in nucleophilic acyl substitution reactions?

Accepted Answer

The chloride ion is a better leaving group than the alkoxide ion.

Question 8

A chemist wants to synthesize a tertiary alcohol using a Grignard reagent. Which combination would be most effective?

Accepted Answer

Reacting a Grignard reagent with a ketone

Question 9

Which of the following is the correct order of acidity for the following compounds: acetic acid, ethanol, and phenol?

Accepted Answer

$$ 	ext{acetic acid} \u003e 	ext{phenol} \u003e 	ext{ethanol} $$

Question 10

Which of the following statements about the Claisen condensation is correct?

Accepted Answer

It requires two esters, at least one of which has an α-hydrogen.

Question 11

Which of the following best describes the product of the reaction between ethyl acetoacetate and methyl iodide followed by hydrolysis and decarboxylation?

Accepted Answer

A methyl-substituted ketone

Question 12

Which of the following is a correct statement about the mechanism of the Dieckmann condensation?

Accepted Answer

It is an intramolecular Claisen condensation forming a cyclic β-keto ester.

Question 13

Which of the following is the major product when cyclohexanone is treated with bromine in acetic acid?

Accepted Answer

2-bromocyclohexanone

Question 14

Which of the following best explains why the α-hydrogen of a carbonyl compound is more acidic than that of an alkane?

Accepted Answer

The resulting enolate ion is stabilized by resonance with the carbonyl group.

Question 15

Which of the following reactions is used in the industrial synthesis of aspirin (acetylsalicylic acid)?

Accepted Answer

Esterification of salicylic acid with acetic anhydride

Question 16

Which of the following is the correct product when ethyl acetoacetate is treated with excess bromine and sodium acetate?

Accepted Answer

Ethyl 2,4-dibromoacetoacetate

Question 17

Which of the following best describes the outcome of the reaction between benzaldehyde and nitroethane in the presence of a base?

Accepted Answer

A nitroalkene via the Henry (nitroaldol) reaction

Question 18

Which of the following is the best method to distinguish between a primary and a tertiary amine?

Accepted Answer

The Hinsberg test

Question 19

Which of the following is the correct product when acetoacetic ester is treated with hydrazine?

Accepted Answer

A pyrazole derivative

Question 20

Which of the following best explains why the reaction of an ester with ammonia yields a primary amide?

Accepted Answer

Ammonia acts as a nucleophile, attacking the carbonyl carbon and displacing the alkoxy group.

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