Question 1

Which of the following carboxylic acid derivatives is the most reactive towards nucleophilic acyl substitution?

Accepted Answer

Acid chloride ($$\mathrm{RCOCl})$$

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{CH_3CONHCH_3}$$?

Accepted Answer

N-methylacetamide

Question 3

Which of the following statements best explains why amides are less reactive than esters in nucleophilic acyl substitution?

Accepted Answer

Amides have greater resonance stabilization, making the carbonyl less electrophilic.

Question 4

Which of the following is the correct product of the hydrolysis of acetic anhydride ($$\mathrm{(CH_3CO)_2O}) $$with water?

Accepted Answer

2 $$\mathrm{CH_3COOH}$$

Question 5

Which of the following is the correct order of leaving group ability (from best to worst) for carboxylic acid derivatives?

Accepted Answer

$$\mathrm{Cl^-} \u003e \mathrm{RCOO^-} \u003e \mathrm{RO^-} \u003e \mathrm{R_2N^-}$$

Question 6

Which of the following reactions is used in the industrial production of soap and involves the hydrolysis of esters under basic conditions?

Accepted Answer

Saponification

Question 7

What is the product of the hydrolysis of benzoyl chloride ($$\mathrm{C_6H_5COCl}) $$with water?

Accepted Answer

$$\mathrm{C_6H_5COOH}$$ + $$\mathrm{HCl}$$

Question 8

Which principle explains why increasing the concentration of water drives the hydrolysis of esters to completion?

Accepted Answer

Le Chatelier's Principle

Question 9

Which of the following is the correct name for $$\mathrm{CH_3COOCH_2CH_3}$$?

Accepted Answer

Ethyl ethanoate

Question 10

Which of the following statements about the hydrolysis of esters is TRUE?

Accepted Answer

Acid-catalyzed hydrolysis of esters is reversible, while base-catalyzed hydrolysis is irreversible.

Question 11

What is the product of the reaction between acetic anhydride and ethanol?

Accepted Answer

Ethyl acetate ($$\mathrm{CH_3COOCH_2CH_3}) + $$acetic acid ($$\mathrm{CH_3COOH})$$

Question 12

Which of the following best describes the resonance in amides?

Accepted Answer

The lone pair on nitrogen delocalizes into the carbonyl, giving partial double bond character to the C-N bond.

Question 13

Which of the following is the correct name for $$\mathrm{CH_3CN}$$?

Accepted Answer

Ethanenitrile (acetonitrile)

Question 14

Which of the following is a cyclic anhydride?

Accepted Answer

Succinic anhydride

Question 15

Which of the following is the correct general reaction for nucleophilic acyl substitution?

Accepted Answer

$$\mathrm{RCOY + HY \rightarrow RCOY' + HX}$$

Question 16

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

Accepted Answer

Conversions from more reactive to less reactive derivatives are generally favorable.

Question 17

Which of the following is the correct product of the saponification of a triglyceride with potassium hydroxide ($$\mathrm{KOH}$$)?

Accepted Answer

Glycerol and potassium carboxylate salts (soap)

Question 18

Which of the following is the correct name for the compound $$\mathrm{C_6H_5CN}$$?

Accepted Answer

Benzonitrile

Question 19

Which of the following is TRUE about the mechanism of acid chloride hydrolysis?

Accepted Answer

The reaction proceeds via nucleophilic attack by water, followed by elimination of chloride ion.

Question 20

Which of the following is the correct product of the reaction between acetic acid and ethanol under acidic conditions?

Accepted Answer

Ethyl acetate ($$\mathrm{CH_3COOCH_2CH_3}) + $$water ($$\mathrm{H_2O})$$

Carboxylic Acid Derivatives: Structures, Nomenclature, Properties, and Reactions

Study Guide - Practice Questions