Question 1

Which of the following statements correctly describes the difference between the two classes of carbonyl compounds shown in the study materials?

Accepted Answer

Carbonyl compounds with groups that can be replaced by a nucleophile include carboxylic acids, esters, acyl chlorides, and amides.

Question 2

Which abbreviated forms are commonly used to represent the carboxyl group in organic chemistry?

Accepted Answer

$$-CO_2H$$ and -COOH

Question 3

In systematic nomenclature for carboxylic acids, which carbon is designated as C1?

Accepted Answer

The carbonyl carbon

Question 4

Which of the following is the correct order of boiling points for the compounds listed below?

Accepted Answer

carboxylic acid \u003e\u003e ester ~ acyl chloride ~ ketone ~ alcohol

Question 5

Which resonance contributor of an ester shows the greatest electron density on the oxygen atom?

Accepted Answer

The contributor with a negative charge on the carbonyl oxygen

Question 6

What is the main reason carboxylic acids and amides have relatively high boiling points compared to esters and acyl chlorides?

Accepted Answer

They can form strong hydrogen bonds.

Question 7

Which of the following statements about nucleophilic acyl substitution is correct?

Accepted Answer

The weakest base is eliminated from the tetrahedral intermediate.

Question 8

Given the following order of leaving group basicity: $$Cl^- \u003c OR^- \approx OH^- \u003c NH_2$^-$$, which carboxylic acid derivative is the most reactive toward nucleophilic acyl substitution?

Accepted Answer

Acyl chloride

Question 9

Which of the following reactions is an example of transesterification?

Accepted Answer

An ester reacts with an alcohol to form a different ester and a different alcohol.

Question 10

Why is acid-catalyzed ester hydrolysis reversible, while hydroxide-ion-promoted ester hydrolysis is irreversible?

Accepted Answer

Hydroxide-ion-promoted hydrolysis produces a negatively charged carboxylate ion that does not react with nucleophiles.

Question 11

Which of the following is true regarding the conversion of carboxylic acid derivatives?

Accepted Answer

A more reactive derivative can be converted into a less reactive derivative.

Question 12

What is the role of the second equivalent of amine (or ammonia) in the reaction with an acyl chloride?

Accepted Answer

It picks up the proton produced in the reaction.

Question 13

Which of the following best explains why the carbonyl carbon is an electrophile?

Accepted Answer

The polarity of the carbonyl group causes the carbonyl carbon to be electron-deficient.

Question 14

Which of the following reactions requires a catalyst because both the ester and the alcohol are poor nucleophiles?

Accepted Answer

Transesterification of an ester with an alcohol

Question 15

Which of the following is the correct product of the reaction between acyl chloride and methanol?

Accepted Answer

$$RCOOCH_3$$

Question 16

What is the effect of protonation of the carbonyl oxygen in an ester during acid-catalyzed hydrolysis?

Accepted Answer

It increases the susceptibility of the carbonyl carbon to nucleophilic attack.

Question 17

Which of the following is true about the resonance contributors of carboxylic acids, esters, and amides?

Accepted Answer

They have two resonance contributors.

Question 18

Which of the following is a correct statement about the mechanism of nucleophilic acyl substitution?

Accepted Answer

The pi bond of the carbonyl group breaks first when a nucleophile attacks.

Question 19

Which of the following is the correct systematic name for the compound with the structure $$C_6H_{11}COOH$$?

Accepted Answer

Cyclohexanecarboxylic acid

Question 20

Which of the following is true about the physical properties of carboxylic acids and amides?

Accepted Answer

They have higher boiling points due to hydrogen bonding.

Reactions and Nomenclature of Carboxylic Acids and Their Derivatives

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